Happy Saturday, Alpaca!

Yesterday, the team was wishing Kimberly a happy 4-year anniversary at Alpaca one day early, and Kaitlynn said:

“4 years?! You basically have a bachelor’s degree in Alpaca!”

Kimberly started as Employee #1 at Alpaca four years ago today, which hardly seems possible. Four years of building our brand, our marketing efforts, and our customer base. Four years of shaping our team culture, our revenue strategy, and our presence in the world. Four years of leveling herself up, making changes when we needed them, and truthfully, helping to shape me into a CEO for the first time. Four years in a start-up truly is the equivalent of a full college education, and then some.

So, at a little celebratory lunch, Kimberly and I ran with the college metaphor.

I asked her the following questions, and then we reminisced and giggled about the answers for an hour. With no further ado…

If Kimberly’s time at Alpaca so far was a college education…

Karen: What did you major in?

Kimberly: “Repositioning.”

This is so true — when Kimberly started, Alpaca was a direct-to-consumer subscription box company with approximately 5 customers. Today we’re a software platform selling to schools and districts. Every step that got us there required us to reposition our products, our value, and our company to each changing audience.

Karen: What “intramural sport” have you played?

Kimberly: “Design: I’m the intramural sports player that takes it seriously and tries to win, even if it’s not the sport I actually trained in.”

Most of our team and customers would never know that Kimberly isn’t trained in design — she brings her keen eye and high standard to every piece of work we put out into the world. Definitely winning the intramural championships over there.

Karen: What is your favorite Alpaca “spring break”?

Kimberly: “Camp Wandawega.”

Can’t argue with this one - this is one of my favorite Alpaca retreats, with one of the most epic photo shoots our team had ever seen. Kimberly was in Wes Anderson-inspired photography heaven, and led the team to such a memorable shared experience.

Karen: What has been your favorite Alpaca “college party?”

Kimberly: “Wilson Phillips karaoke after winning the day at NCE.”

Funny enough, this is also what 80% of the team said was their favorite memory of Kimberly from this year. I’m not even going to try to explain this one, but Kimberly said it well: “There’s no celebration like celebrating after a big win.”

Karen: What is your most memorable “all nighter” at Alpaca?

Kimberly: “October 2022 packout“

We had an overly ambitious Alpaca pack, not enough hands, and new customers that we’d promised an on-time delivery. (And I do mean delivery — we delivered all of our packs by hand then). In case you’re on the team and don’t know the provenance of our obsession with Mariah Carey, it is this night. We had one goal after that experience: “no more midnights.”

Karen: What is your go-to “cafeteria meal” at Alpaca?

Kimberly: “Egg Bites, of course.”

I think I’ve seen this woman eat approximately 200 egg bites in the last four years. It’s honestly remarkable.

Karen: Who has been your hardest “professor” at Alpaca?

Kimberly: “Customers who tell us no.”

I love this answer so much. Kimberly went on to explain it: “Listen, I think we’re really amazing. So if someone doesn’t, and they say no to working with us, I really want to know why. Could we have done something different? Did we not create the right relationship? Is our product the wrong fit? Is it really because of budget? Those are the questions that teach me the hardest lessons, and the ones I value the most.” <— May every startup company have early employees who think like this.

Karen: What do you want to get your “masters degree” in at Alpaca?

Kimberly: “Answering the question ‘What should we do next?’”

This answer pretty much sums up exactly where Kimberly is in her world at Alpaca right now: shifting from the purely tactical to the grounded strategic; from the fully experimental to the “we’re starting to understand what our customers truly want and need;” from a die hard member of the squad to the leader of a growing and evolving team.

Kimberly, if the last four years were a college education, I believe you would be graduating with highest honors with all the special lanyards and cords. You bring the highest level of rigor, excellence, joy, and love to every single bit of work you do for this company.

This year alone, we saw you lead our marketing team, run a summer camp for educators, take Alpaca to 34 conferences, roll out our largest presence at an event, and then casually run 2 marathons and earn a literal masters degree.

We’re us because you’re you, and I cannot wait to see what extraordinary work we have in store together in Year Five. Happy Anniversary, and THANK YOU for every single way you shape this company.

Love,

KB

At Alpaca, our #1 core value is Listen to Teachers.

It’s what our entire company was built on. Before we even started the company, I wanted to make sure I wasn’t inventing a solution for a problem I didn’t understand. So before I wrote the plan, I took coffee to dozens and dozens of teachers after school. I toured their classrooms, sat down in their tiny chairs, and said “Tell me about your work as an educator.”

We built our very first teacher recognition program based on what we heard in those classrooms, and we’ve built every product and feature since based on listening, listening, listening to teachers.

Late last year, we realized we had the opportunity as a company to listen in a bigger way. In December, we put out a call to our Little Wins Newsletter list (mostly school and district leaders) to take our School Culture Survey, an in-depth listening survey to understand where leaders feel great about their school culture, where they’re challenged, and what they see changing. We were overwhelmed with the response!

We then realized that we could analyze the leadership survey data alongside the pulse survey data we get throughout the school year from teachers, as well as the in-depth interviews we’ve done through the Little Wins Podcast’s first season, to create an unprecedented look at school culture in the US, right now.

Today, we’re publishing The School Culture Report 2026, and you’ve got the first look at it!

Download The School Culture Report 2026

I’m beyond excited! Here’s what’s inside:

Whose voices are here

There are a lot of voices in this report, friends. Here’s what you’ll find here:

• Pulse responses from 33,144 educator surveys across 280 schools and 34 states, gathered over eight months (August 2025–March 2026).

• A national survey of 155 school and district leaders across 35 states. Every role on campus — classroom teachers, paraeducators, specialists, school staff, administrators — is in there. Every community type, too: rural, suburban, urban. It’s the most representative listening exercise we’ve ever done as a company.

• 38 interviews with school and district leaders from the Little Wins Podcast

What we learned

Where to start!? When we combined these different voices (educators and leaders at the school and district level), we saw a unique look at what’s happening in schools today. Here are some of the biggest things we learned:

For me, there were a few important takeaways:

Health and wellbeing is the big story.

Across ten wellbeing themes we measured, the area where educators expressed more negative sentiment than any other was their own health and wellbeing. And when we asked leaders which area of school culture they find hardest to support right now? The very same thing.

“The pace hasn’t slowed, expectations keep stacking, and people are tired in a deeper, more cumulative way,” said Danae Acker, Instructional Coach at TL Hanna High School in Anderson, S.C.

So we have leaders everywhere who know their teachers’ health is the thing, and that is the thing they feel least confident about how to support. And yet, our leaders do know what does move the needle for school culture: relational leadership that emphasizes connection and personal relationships.

Connection is winning. When leaders told us what’s getting better in their school culture right now, the #1 answer was staff connection and collaboration. 27% of leaders named it as the single biggest improvement in their school culture.

“Relationships are the key — I make a point of touching base with every staff member at least once a day, to ask about something personal or professional, but just to talk to them,” said Julie Pearson, principal at Nathan Hale Elementary School in Whiting, Indiana.

The leadership practices leaders themselves named as most impactful for school culture — presence and visibility, 1:1 management, consistent communication — are the exact practices they wish they were doing more of. Leaders know what works. They are, by their own admission, doing less of it than they want to. “Leaders are stretched, and the relational work is the first thing that gets squeezed” is the way we heard it directly from the leaders.

The work in front of school leaders today is to find opportunities for the connective, relational work that they know builds stronger culture. That’s what the back half of the report is about: ten leadership practices, filled with some of the best practices in school and district leadership we’ve heard. This section has real examples, tips and ideas, and key insights about leadership practices like 1:1 management, communications, meetings & gatherings, and seven more.

I’m so excited for you to read it, share it, and for us as a company to continue to learn from it. I’ve read every single response from leaders in building this report, and I hope you’ll read it with a pen and highlighter in hand and the question in your mind:

“How can we use this listening to build Alpaca to support what leaders need today?”

A massive thank you to the Alpaca team — every one of you put hands on this in some way: on the survey, the writing, the design, the imagery, the editing, and the support to make sure we’re representing each voice with accuracy and care.

I hope you enjoy learning from this report, and finding new ways to connect to our core customers through this resource. Here’s my ask of you:

When you see or meet one of the 155 leaders who answered our questions, the podcast guests whose ideas helped shape the practices, and the thousands of educators whose voices anchor every page of this thing: tell them thank you.

And then buy them a coffee, go visit their classrooms, and listen some more.

With Gratitude,

KB

There’s a famous story by Brad Isaac about meeting the comedian Jerry Seinfeld. Isaac was a software developer and aspiring comedian, and he recalls that at a comedy club one night, he Seinfeld his advice for a young comic. The answer was this:

1. Purchase a large, one-year wall calendar and a thick red marker.

2. Every day that you write (even if it’s just one joke), put a big red ‘X’ over that day’s date.

3. After a few days, you will see a chain of red Xs. The only goal is to not break the chain.

It’s the premise on which a lot of modern productivity advice is based — little habits, done often, create little gains that add up to big change. It’s what our work is based on too — Little Wins, anyone?

So, back in January, you may recall that I asked you the question “What will you do 100 times this year?”

Our company goals are fantastically audacious and I think the best way to achieve them is with great habits — things we do every day. So my personal goals for the year are centered around creating excellent habits that make the work of building a successful company and a healthy personal life feel less like a Big Initiative, and more like muscle memory.

Last week we saw the 100th day of the year (can you believe it!?) so I took a moment to take stock of what I set out to do this year, where I am on those habits, and how I might focus or change for the next 100. Yes, I made a sticker chart. It’s fine.

Here’s what I’ve learned so far, personally:

Mondays are where I shine. I start off the week really strong in my habits and find myself waning by end of week, and sometimes crashing into the weekend on Fridays. I think figuring out how to get a bit of a reset mid-week would help even this out.

Habits really do stack. James Clear taught us this in Atomic Habits and it’s always made sense in theory to me: creating a small habit and then attaching another one to it creates a high impact chain reaction. When you have a habit to see the sunrise, it’s much easier to add a 1-3 mile run each morning, because you’re awake for it! What I found in my data so far this year is that I have days where I knocked out 7 or 8 of my habits, and days where I put up 0. I’m excited to see what I can easily add to my established ones to stack some more, especially in the areas that I’m scoring low today. Like eating breakfast.

Habits need accountabili-buddies. Well, at least MY habits need friends and family to help me keep them. Every habit I have successfully built up this year so far, I’ve done with at least one other person. I talked to 60 potential customers because our team diligently set meetings for me. I see the sunrise most days because I’ve committed to meeting running friends at the gym. One of the most powerful things I can do going forward is to just ask one person: “Can you help me with this habit?” That’s easy enough for anyone to do. Need a buddy for a goal? Ask me, please! I’m honestly so grateful for those who are helping me with mine.

What I’ve learned has already been helpful. But like all habits and goals, the key is to a) keep working on them with honesty and transparency; and b) edit them based on what you learn. Here’s how my next 100 days of the year is focused:

1. I’m keeping the real goal first. Consistency without quality may be counterproductive, it turns out. I’ve run 108 times this year, but if I’m being honest, sometimes I got out there for 1 dumb mile just to keep the streak alive. It did the job of creating the habit, but it did not improve my running, like at all. On running and strength, I’m shifting my focus to “quality workouts every day,” and working with a coach who can actually help me improve. Running garbage miles wasn’t getting me to my real goal, which is to improve my running and my fitness.
   
   The real goal in the company? Growth. If what we’re doing isn’t working, the answer is not to say “that’s not working” — the answer is to make our own luck. We learned that in Nashville, and we’re bringing it front and center this quarter.

2. I’m asking for more help. More buddies, please. For the next 100 days, I’m looking for ways to engage more people (and more robots?!) in my goals, and to stack them in smart and creative ways. I started this week by asking my friend Claude for help with coming into conversations with potential customers with a greater level of hospitality, and it’s amazing what’s possible.

3. I’m tracking what’s easy. I’ll drive myself nuts if I try to keep track of or write down every time I make dinner for my family or text or call my parents. So, while I’m keeping some of those “hard to track” goals in mind and looking back at them regularly, I’m not tracking it all. I’ll track what’s already being recorded on my watch and my work apps, and “gut check” the rest.

   (Also, using Claude to analyze your goals against your Strava exercise data, Garmin sleep data, NYT Crossword data, and Hubspot sales data? Nice little Saturday morning. Highly recommend.)

I’d love to know where your goals are this year, and how I can support you with them! Let’s grab coffee after sunrise but before customer meetings start and talk about it — it’ll be a stacked habit we’re both proud of.

Let’s go, Alpaca — big things to do!

KB

PS: Were you wanting the actual score card? Here are my current stats on the “hundreds” I set forth.

Work Goal: Our company’s goal is to grow customers, revenue, and team by 100% in 2026. The things I PERSONALLY want to do toward that goal:

• 100 meetings with education leaders: Currently at 55 held meetings with education leaders, 2 podcast recordings, and 3 customer meetings, so I’m counting 60 total. Good start for the year, but we can do more.

• 100 handwritten thank you notes: I’m at 10. This one needs work. Perfect candidate for habit stacking — adding 15 minutes for this practice after interviews, meetings, and demos would be easy enough.

• 100 new customers: So far, we have added a little more than 20 new customers, so we’re sliiiiightly off where I wanted us to be by April. Not to worry, we’ve got a team, a plan, and a great leader to help us get there (and so much more).

• 100 returning customers: It’s renewal season now! So this work is just beginning.

• 100 published posts/articles: Well guys, this one has fallen short, with just 13. Time to fire up the writing a little more often.

• 100 investor conversations (current or future): I’m so lucky that we are at 20 here, but closed our bridge round in record time!

• 100 team 1:1s: If I’m counting correctly, I’m at 38. My favorite ones this year? Hands down, it’s Excel School, the every other week mentoring meeting I do with Kaitlynn to discover how we can be more AI and data conversant in every aspect of our work. (It started off in spreadsheets but we’ve evolved!)

PERSONAL

Personal Goal: Be consistently ready to run a half marathon (healthy, strong, nourished), enjoy excellent relationships with every member of my family, and take care of myself.

• Hit a 100 day running streak: I technically didn’t do it yet. I ran 100 days in the span of 102 days, but I missed 2 days due to international travel.

• 100 breakfasts: I think this number sits at 4? I may need a breakfast streak.

• 100 strength workouts: Started off a little slow, so I’m at about 12. This is a big priority for me this spring!

• 100 pre-10 pm bedtimes: Possibly my worst data point besides breakfasts. I have 12.

• 100 sunrises 🌅 CRUSHING IT! at 78 so far this year. Being up early is the literal best.

• 100 pieces of art made (any size!): Failing it! I’m at 5. Maybe 6, if you count the sticker chart that I made for my goal tracking. Thanks to Marina for making art part of our birthday happy hours, though! Those are 3 of my 5. (Wait Marina did you do that on PURPOSE!?!? You probably did.)

• 100 books read: This is a ridiculously audacious one, but I’m at 13. Did you want my favorites? Thank you for asking! Fiction: Theo of Golden. If anything surpasses it this year, I’ll be shocked. I loved it so much I’ve read it twice already. Non-Fiction: Unreasonable Hospitality. You won’t believe how this changes your mindset at work, honestly.

• 100 NYT crosswords completed: I’m at 62, and I’m quite pleased with this new habit in my life. It helps me feel sharper, it’s a fun thing to do with a friend, and the New York Times games app is just incredibly encouraging.

Thank you for your time last week at All Hands, Mini Hack Day, and Board Meeting — what a week! Q1 was one of our greatest learning quarters as a company. We won fantastic new customers, launched product features that make me smile every time I see them, and grew our leadership team with an eye on the future. There were more than a few moments that reminded me why we’re building this company in the first place, so I wanted to share them here!

Q1 Highlights

Our customers are growing with us, and seeing true positive change

I want to highlight one customer story that captures what we’re building toward. Council Bluffs Community School District is in their third year of partnership with Alpaca. Over time, we’re seeing a correlation of lowered teacher absenteeism with higher levels of positivity in the district. And most importantly: all 11 participating schools improved their positivity year over year. All of them!! We’re learning so much from the Council Bluffs team, and I’m so excited to continue to grow and learn together.

We crossed 500,000 Pulse insights.

This one is a quiet milestone that I think is actually enormous. We’ve now collected over half a million data points from educators across the country — giving Alpaca a true seat at the table educator in the emerging conversation on wellbeing and school culture. That data is the foundation of something big: our first School Culture Report, due out later this month. (More on this soon!)

Shoutouts came to life.

We officially launched Shoutouts — a simple, peer-to-peer recognition system for schools and districts — and educators have already shared more than 4000 shout-outs with their peers. Teachers and school leaders are using it to recognize each other in personal, meaningful ways. These aren’t automated “great jobs” but real, human, specific moments of gratitude.

We showed up big for education’s biggest conference

Our team showed up strong in Nashville for the AASA/NCE Conference! We booked over 100 demos with future customers with our largest presence at a conference ever. The booth was buzzing, the conversations were meaningful, and the energy was incredible. We learned how to talk about our product in new ways, and the “jobs to be done” for school districts.

Sales leadership to grow our future!

Jessica Johnston-Myers joined the Alpaca team as our Chief Sales Officer, full-time in March, and you already know — she is already making a huge impact. She’s hired and built our current SDR team and is bringing a level of rigor and ambition to our go-to-market that we’ve never had before. I cannot wait to see what this growing team is going to do in Q2!

What’s Ahead in Q2

We’ve got a HUGE quarter ahead! Here’s what we’re investing our energy in:

We’re launching major product updates — including the Little Wins Library, some new district tools and views, and improvements to Alpaca Pulse. These are the tools school leaders have been asking for, and I can’t wait to get them into their hands.

We’re publishing the 2026 School Culture Report — our first industry report on school culture and educator wellbeing, powered by 500,000+ teacher voice data points and 155 leader surveys. I am so excited to share what we’re learning by living our #1 company value: Listen to Teachers.

We’re hosting our first Little Wins Workshop — a customer and user conference designed to deepen relationships, gather feedback, and build community among school leaders using Alpaca. The speaker line-up is incredible, and I cannot wait to see leaders come together for this event!

We’re continuing to grow the team (know anyone looking to join an amazing sales org!?), learning from our customers, and building relationships with school and district leaders through events, conversations, and opportunities to build great tools together.

We’ve never been better positioned. And I’ve never been prouder of this team.

Let’s go make Q2 count!!

KB

Today’s a fun day — we’re launching one of our largest single product features we’ve ever built — Shoutouts!

For the last few months, our Alpaca team has been testing out Shoutouts each week when we do our own Alpaca Pulse survey. It’s a simple step at the end of our pulse survey to take one moment to recognize another member of our team. Just write your shout out, see it on our dashboard, and if you want, make a postcard to share.

The recognition is anonymous. There’s no reward attached, no leaderboard, no program. Just an open door to say something kind about someone you work with.

Pun intended: BIG huge shoutout to Maci and Alissa — this feature was part of their Hackday project back in October, and look what it has become!

So far this year, our small team sent 100 shoutouts to one another. So of course I did a little analysis (nerd alert!) on those shoutouts. I wanted to see what the nice things you said to each other could tell us about our year so far.

Here’s what I learned:

We talk about growth the way great teachers do.

When someone on our team is praised for being “open to feedback and willing to take coaching,” or for “pushing herself outside of her comfort zone,” the tone isn’t evaluative — it’s celebratory. Growth at Alpaca is spoken about the way great educators speak about a student’s breakthrough: with warmth, with pride, and with the understanding that the courage to stretch matters more than the outcome.

People here notice when a colleague refines their pitch or learns a new framework — because we’ve built the kind of safety where being a work-in-progress is something to celebrate, not hide.

We notice the work behind the work.

So many of these shoutouts celebrate the invisible labor that holds everything together. Keeping a software platform running 24/7. Coordinating conference logistics down to the last swag bag. Screening candidates with warmth.

Our culture doesn’t just value the big wins — the booked demos, the closed deals, the shipped features. It values the connective tissue: the person who makes the trip feel effortless, who keeps the data accurate, who makes a new candidate feel excited rather than anxious. I love this about us.

Care is the work, and the work is care.

It’s hard to know where our work stops and our relationships begin. Cooking a team dinner together appears alongside booking four meetings before noon. Airport pilates sits next to conference booth strategy. Someone is celebrated for “cutting the chicken for team dinner” in the same breath as “keeping us close to teachers and leaders in real time.”

The care we extend to each other — a ride home, a bit of encouragement, sticky notes left on a desk — is the same muscle we use when we build products and show up for school leaders at a conference.

Joy is a practice, not a byproduct.

Joy shows up constantly in these shoutouts, but not as something that just happens to this team. It’s something we build. March Madness brackets. Thank you note parties. Collaborative cooking. People aren’t credited for being joyful — they’re credited for creating conditions where joy can exist, even in the middle of a demanding week.

When we build products for educators whose top words include “fatigued” and “exhausted,” this instinct matters. If we know how to create genuine care inside our own team, we’re far more likely to build something that does the same for the people we serve.

Now — what’s missing.

I wouldn’t be doing this analysis justice if I only told you the pretty parts. We can also learn a lot by noticing what we didn’t recognize each other for. So here’s what I noticed in the gaps:

Let’s celebrate the impact, not just the effort

Our shoutouts are almost entirely about effort and presence — rarely about outcomes. We praise each other for working hard and showing up, but almost never for a specific result or a measurable difference made for a customer. Learning to celebrate impact alongside effort is an important edge for us.

More cross-department recognition

Most recognition stays within departments. There isn’t much flowing between, say, Engineering and Customer Success, or Marketing and Sales around shared wins. As we grow, those cross-team connections are the ones we need most.

Let’s say the hard stuff

In our shoutouts so far, nobody is praised for navigating something hard, failing, or recovering. We celebrate stretching — but not resilience through difficulty. No “we hit a wall and you helped us figure it out.” We have safety around learning, but we’re still building comfort around vulnerability in the face of actual failure.

Everyone is a leader

Our shoutouts so far don’t tell much about peer leadership. Shoutouts about leadership qualities cluster around our managers, with very little recognition of peers stepping up to lead a project or hold each other accountable. That distributed leadership muscle is going to matter a lot as we grow. Let’s look for it, recognize it, and encourage it.

Here’s what I know is true: recognizing each other makes a difference.

100 shoutouts so far is a tiny data set, and I cannot wait to see what a full year of shoutouts reveals about our company. But even in 100 little anonymous moments, the picture is vivid: this is a team that celebrates growth over perfection, notices the work that others miss, refuses to separate caring from doing, and treats joy as something worth building on purpose.

Congratulations to the WHOLE team for the launch of shoutouts — let’s keep building positivity together!

KB

Imagine yourself at 80 years old, reflecting on your career. Ask yourself: What in my work life gave me a sense of fulfillment and meaning?

If you’ve ever been a part of a performance review, I’m guessing this question wasn’t a part of the process? What gives you a sense of fulfillment and meaning? What does THAT have to do with how you’re doing at your job?

Your values have everything to do with your job performance, actually.

Because when our work gives us a sense of fulfillment and meaning, we inherently do better work. And performance reviews are about one thing: helping each of us do better work.

I discovered this question, and the Values Exercise, when I read Claire Hughes Johnson’s book Scaling People, and it’s arguably the best leadership book I’ve ever read. She adapted an exercise for the team at Stripe from Stan Slap, a leadership coach for companies all over the world.

The idea is fairly simple: to understand the best work each of us can be doing, we must first identify what our values are in our work.

Why? Because we spend a lot of time at work. And if you’re going to spend a huge amount of your time with Alpaca, you should find your personal values reflected in your day, every day.

Stan Slap says it better than I could:

“To not live your deepest personal values over half your life at work is a crime. Worse, it’s a preventable crime.”

— Stan Slap

If your personal values are around achievement, courage, and mastery, I want your time at work to be spent taking some big risks, learning new skills that support the company’s goals, and winning. If your personal values are around listening, connection, and integrity, I want you to apply your precious hours with Alpaca finding new ways to listen to and connect with educators while creating authentic and genuine experiences and connections.

This week, we’re going to engage in a different kind of “performance review.” Rather than starting with “are you doing a good job at your job as defined by your job description?”, we’re going to engage in an exercise that helps us understand three things:

1. What in your work life gives you a sense of fulfillment and meaning?

2. What are the top core values that are represented in your imagining of your fulfilled life (e.g., excellence, joy, balance, community, impact, learning).

3. What do you need to be doing at work to ensure you’re both supporting the needs of the company while living your deepest personal values at work?

The coolest part? Understanding your values helps your manager support you to be super successful in your role. Many (probably most) of our roles at Alpaca can be accomplished successfully in different ways. In a way, understanding your own values makes every role here completely unique. Think of it this way:

Your personal values + Alpaca’s company goals = Your job description

Finding your way of working that a) accomplishes our company goals and b) honors your values — that’s the work you and your manager have in front of you, and it’s the purpose of this exercise.

It’s not a one way street, either. You’re going to learn a lot about your values (of course), but you’re also going to learn what your manager and what our leadership team values too.

I encourage you to get curious about that question, and understand the values your leader holds most dear. Together, you can work toward the work that helps you both live your values every day at Alpaca. Again, Stan says it really well:

“You cannot live your values without the support of your people.”

— Stan Slap

Alpaca, I can’t wait to learn more about what makes you tick, what gets you out of bed in the morning, and what Future You looks like when you’re living your values while achieving our goals together.

Let’s keep going — it’s going to be a big, fun week!

With Gratitude,

KB

PS: Want to dig in more? Here are some extraordinary talks, books, and resources. Remember, Alpaca will buy you any book that helps you do your job better. Just ask - it’ll show up on your desk in a day or two.

Books:

• Scaling People by Claire Hughes Johnson: Like I said - this is one of the best leadership books I’ve ever read, and it’s a reference guide on my shelf. If you’re interested in leading people, get this book.

• Bury My Heart at Conference Room B by Stan Slap:

Talks & Sites:

• Learning Omnivores: How the Values Exercise is used with school principals

• Stan Slap talks at Google (17:25 is where he talks about this type of values exercise):

PPS: If you’re applying for a job with Alpaca right now, you’ll find the full exercise we’re doing at this link. Feel free to send us your top three values at careers@getalpaca.com.

The first day that I met Jessica Johnston-Myers, I knew there was something about her work that would become essential to our work at Alpaca.

It was in the very early days at Alpaca when I was invited to visit Apptegy, a company we all know is an aspirational leader in the education space. I was hosted by their Marketing leader (another of Alpaca’s great mentors!) and Outbound Sales leader — Jessica Johnston-Myers.

I am not exaggerating when I say I filled a notebook with learning about how she approached district level sales, events, and outbound sales — their approach was focused on both the relentless pursuit of growth, and extraordinary hospitality.

I wrote all about it in a Team Letter more than 3 years ago — you can check it out here if you haven’t read that one:

In many ways, Jessica was “working” at Alpaca long before she was working with Alpaca.

Last year, when we got the opportunity to work with Jessica as a consultant to help us build our sales team, I didn’t hesitate. I asked her to design and hire the first official sales team, set the expectations for how we do work, and question everything about how we’ve done things to date.

Well, she did. And on some days, it was terrifying.

She handed me hiring plans I couldn’t even imagine being able to accomplish. She gave us new scripts and strategies for our booth at conferences that we were scared to try. And she set expectations for sales activity that we’d never once come close to hitting before. And when I told her I was nervous about those plans, she asked me one question:

“Do you want to win, or don’t you?”

Well, after that, we did what she said. And we started winning. As a leader of a start-up, it’s both the most terrifying thing in the world and the greatest gift to have a leader who is much better than you at something step in and show you how it’s done.

That’s why I am so excited to welcome Jessica to the Alpaca team full time today, as our first Chief Sales Officer. Jessica will lead the sales effort at Alpaca, working closely alongside our VP of Marketing and myself, and together, we have BIG dreams ahead for the future of growth at Alpaca. (oh, and we’re hiring!)

It’s because of watching joyful SDRs make videos for superintendents that I knew that with Jessica, we could bring our silliest, craziest ideas to the world of school district sales.

It’s because of watching Jessica’s high expectations of the professionals who work on her teams that I knew our ambitions would match up. (And that Jessica could level ME up too!)

And it’s because of the effusive praise I heard from the members of her team (who did not know that I knew her) that I found confidence that Jessica would be a sales leader I would trust with this company’s most prized asset — our team.

Please help me welcome Jessica to the team full time — let’s go WIN TOGETHER!

KB

Do you remember our Post-Day 1 conversation in Nashville? Of course you do — it was a big moment of honesty and trust about work that was going better, but still wasn’t going quite the way we wanted. We listened, we offered ideas, and then we went out and made Day 2 amazing.

In a way, what you experienced there was a very informal, but high trust, project retrospective. And that’s what we’re talking about today — Project Retrospectives!

Going forward, we’re going to build a regular practice of Project Retrospectives at Alpaca — simple, brief conversations where the team that worked on something comes together to talk about what happened, what we learned, and what we want to do differently next time.

We’ll be starting with Event Retros this week, and Kimberly will be showing you a simple template for these at this week’s All Hands meeting. So before we jump into that today, let’s get everyone on the same page about what these are, and why we do them!

What is a project retrospective?

A project retrospective (retro!) is a regularly occurring meeting that happens at the completion of a project or event. The attendees should include all active project participants and all project stakeholders and decision-makers.

A retro should occur as quickly after the completion of a project as possible, so as to maximize learning while it’s fresh.

Why do a project retro?

The goal of a project retrospective is to get the participants of a project together to build a common understanding of the successes and challenges of that work, so that everyone can learn and improve upon the next one.

To be succinct: the goals of project retros are twofold:

1. Shared ownership of a project’s result and

2. Shared understanding of how to improve future performance.

A good retro is a high trust engagement

To accomplish these two primary goals, retros need to be high-trust engagements.

Everyone in the room should feel able to talk candidly about what went well, and tell the truth about what happened. And everyone means everyone.

That means:

• No blame games.

• No defensiveness.

• No pretending everything went perfectly.

At the same time, this doesn’t mean retros are soft or vague. They should be honest, thoughtful conversations about real work.

There should be room for celebration. There should also be room for accountability. Trust is what allows both to exist at the same time.

Guidelines for a high trust retro

Creating an atmosphere of high trust isn’t about holding hands and doing trust falls.

A “high trust” retro should be a rigorous review of the project, with participants taking clear ownership for execution that needed improvement, and with stakeholders taking clear ownership for changes to scope or expectations. There should be room for celebration, as well as accountability; learning, as well as clear planning for future success.

Here are a few things that will help everyone take the best next step.

#1: Always do them, and use the same exact format every time.

One of the best ways to create trust is to ensure that everyone knows what they’re getting into every time they walk into a retro. So, starting this week, we will do a retro for every event we attend and use the exact same format every time (you’ll find our event retro format on Alpaca Notion in the link).

It’s important to not just do retros when the result is less-than-ideal. Doing retros only if we missed a goal would have two results:

1. People will be afraid when a retro is called; and

2. Successful projects will not get proper celebration and learning, which is demotivating for everyone.

When it comes to asking the same questions every time, some of those questions will feel difficult at your first retro. But if you set it up as “hey, so some of these are hard questions, but they’ll get easier every time!”, you’ll see trust in the process.

#2: Say what you said!

In a retro, make sure there’s no revisionist history — like “we said we’d launch these 3 features, not all 5 of them — those other two were nice-to-haves.”

Clearly say what you said you’d do, and on what timeline, and how you objectively performed against those commitments. Try these three discussion questions:

1. What exactly did we say we would do?

2. What are our results against those commitments and timelines?

3. Did we accomplish anything NOT on our list of commitments?

#3: We’ll celebrate and improve at the same time

A retro shouldn’t be divided into a “celebration section” and a “problem section.”

The real story of any project is always mixed.

Great teamwork might exist alongside a confusing timeline.
A strong launch might happen despite some messy coordination.

So instead of separating those things, we’ll talk about them together.

We want to notice:

• Who helped make something difficult easier

• What we’re proud of

• What we’d approach differently next time

#4: Retros are about the work - not individual performance

Retrospectives focus on how the project unfolded, not on evaluating someone’s job performance.

If someone on the team needs a performance conversation, that should happen privately and directly — not in a group retro.

The retro is about understanding the system around the work:

• priorities

• communication

• timelines

• expectations

• resources

When we improve those things, everyone does better work.

#5: Listening matters as much as talking

People who were deeply involved in the project will naturally have more context to share.

People who were less directly involved may have a different role — often to listen, ask thoughtful questions, and help the team reflect.

One way to think about it is a talk-to-listen ratio.

If you were close to the work, you’ll probably share more.
If you were more removed, listening is often the most valuable contribution.

Ready to try it yourself? Here’s how.

I encourage you to try out a retro for an event, product release, Alpaca resource set, a team event, or sales campaign soon. You don’t need permission - just give it a try. To get started on building a retro for a project you own, here are some frameworks and questions you can try:

Five Great Retro Frameworks

• Start, Stop, Continue: A straightforward method asking what actions to begin, cease, or maintain.

• 4 Ls (Liked, Learned, Lacked, Longed For): Promotes nuance by exploring what team members enjoyed, discovered, missed, or desired.

• Sailboat (Speedboat): Uses a metaphor to identify what propelled the team (wind), what slowed them down (anchors), and risks ahead (rocks/pirates).

• Glad, Sad, Mad: Encourages emotional reflection by categorized feedback into what made the team happy, disappointed, or frustrated.

• ORID (Objective, Reflective, Interpretive, Decisional): A structured approach for facilitators to guide the team from facts to decisions.

8 Questions for Retros

1. What problem were we trying to solve with this project?

2. Do you think we set the right goals with this project, why or why not?

3. What are you most proud of in this project?

4. What is one thing you wish you’d known before this project started?

5. Who is someone who helped you during a challenging part of this project?

6. What is one thing you’ll ALWAYS do on future projects, and one thing you’ll NEVER do on future projects?

7. What is a resource you wish we had to help our projects work better?

8. Active project participants, what do you need from stakeholders? Stakeholders, what do you need from project participants?

One last thing

Occasionally, we’ll want to step back and retro the retros. So if you’re participating in some over the coming weeks, think about these questions:

• Are they helpful?

• Are the questions useful?

• Is the format working for the team?

If something could make them better, say so and let’s adjust!

Like everything else we build at Alpaca, the goal is steady improvement.

Every project is a chance to create something valuable, but it’s also a chance to learn together. Retrospectives are simply our way of making sure we don’t leave that learning on the table.

Let’s get out there this week, Alpaca! 🦙

KB

And when you’re planning a retrospective for a project, an initiative, an event, or a campaign, it can be helpful to use the same format each time, so that people understand what to expect and feel safe sharing it. I’m a big fan of Miro — they create collaborative software for teams. Their blog focuses on great strategies to create more shared decision making and collaboration among teams. Their article on retrospectives is a fantastic read with great retro frameworks. Here are five that I think would work well for our team (and so many others!)

Top Retrospective Frameworks

• Start, Stop, Continue: A straightforward method asking what actions to begin, cease, or maintain.

• 4 Ls (Liked, Learned, Lacked, Longed For): Promotes nuance by exploring what team members enjoyed, discovered, missed, or desired.

• Sailboat (Speedboat): Uses a metaphor to identify what propelled the team (wind), what slowed them down (anchors), and risks ahead (rocks/pirates).

• Glad, Sad, Mad: Encourages emotional reflection by categorized feedback into what made the team happy, disappointed, or frustrated.

• ORID (Objective, Reflective, Interpretive, Decisional): A structured approach for facilitators to guide the team from facts to decisions.

As you may know, we’re working right now on the Alpaca School Culture Report, a deep dive into the state of school culture, according to the leaders and educators experiencing and building culture today.

As part of that work this weekend, I revisited my favorite learning on culture — the HubSpot Culture Code.

I love learning about how great companies build their cultures. A few years ago, I heard Dharmesh Shah, cofounder of HubSpot, talk about the hundreds of hours he has spent on an internal project — and product — called the HubSpot Culture Code.

Why would HubSpot’s Chief Technology Officer put such a huge focus on company culture, something usually owned by People Operations or “HR?” Because it’s that important, and Dharmesh makes a point of spending his time on the most important work of the company.

The result — The HubSpot Culture Code — is not just a manifesto or handbook — it’s a product, built for HubSpot’s employees. They’ve published the entire thing online, they’ve revised it 41 times (seriously!), and it’s worth reading once a year.

They call it the “operating system powering Hubspot” and I love that concept — that culture is the operating system that powers our organizations and teams.

Here are my favorite takeaways:

• “We’re building two products: one for our customers, and one for our employees. Culture is the product we build for ourselves.” YES, and this is true for schools, too. What is the culture product that teachers and principals are building for themselves? This has my brain going!

• “Culture exists whether it’s intentional or not.” Every company has a culture. Whether you’re intentional about designing the one you love is up to you.

• SFTC: “Solve for the Customer.” I love that the first tenet of an internal culture document is all about a relentless focus on the customer.

• Courage over comfort. Boldness over hesitation. Simply put, and a clear directive — HubSpot does such a service to its employees by being so clear with expectations of how to approach problem solving.

  

• “It’s not an open door policy. It’s a no door policy.” The idea that every employee has access to every other; that “debates should be won by better insights, not bigger job titles;” and that “transparency ≠ democracy” hits all the things employees desire in transparency, while addressing all of the things that create concern for company leaders.

• Use Good Judgment. This three word policy replaces most policies in the company. If you’re wondering where I get my opinions about having a lot of “policies,” it’s here.

• Customer > Company > Individual: HubSpot calls this the “cheat sheet on good judgment.” Don’t solve for your personal interests over that of the team, and when in doubt, solve for the best interests of the customer. If you remember one thing from the Culture Code, make it this.

• “Humility isn’t about thinking less of yourself. It’s about thinking of yourself less.” That’s the best definition of humility that I’ve heard.

• “We like learn-it-alls, not know-it-alls.” Stealing this.

• Free Books Program. “Request a book, it magically shows up in your inbox. No expense reports required.” What better way to encourage learning than that. Again, now you know where I got this practice!

Overall, one of my favorite things about this product is its simplicity: it’s an openly published slide deck, with a total of 58 slides, many of which have fewer than 10 words on the slide. That’s intentional too — because nobody has time for a 100 page manifesto, and if they did have time to read it, they wouldn’t remember it.

And culture is only as strong as the choices and values you remember and repeat.

Need a fun challenge this week? Spend a little time thinking about what values or choices YOU would put in a Culture Code product for Alpaca. If you do, let me know so we can grab a coffee so you can tell me about it!

On the flight home from our time together at the National Conference on Education in Nashville on Saturday, I had to take a minute to write down what we learned and did together this week. It’s why I write Team Letter — to not forget the little moments of the company that I feel we’ll look back on one day and say “that was a turning point.”

Last Friday was one of those turning point days.

I try not to lean into hyperbole, so you know it’s genuine when I say — I feel like the ground shifted underneath this company last week, in the best possible way.

I have always believed that our product has important work to do for schools and districts. And I have always believed in our brand, our mission, our values, and the opportunity ahead of us. But this week, I watched something new emerge in the company:

I watched our team go from being a group of people who work together to a true team of owners.

I will say, it didn’t happen in a glamorous way. It actually happened because we struggled and sweated through some things. Early in the week, we struggled to get our presence set up at the conference — it took us hours longer than we expected, and included a trip to a production studio, several emergency Amazon orders, splitting up the team for dinner, and making some last minute changes to make everything work. Thank goodness for portable steamers.

We struggled, too, the first day of the conference. We watched the companies whose success we aspire to fill up their booths with conversations and connections and booked meetings, while ours floundered a bit. We took a stutter step. We didn’t engage. We got scared out there and then we got in our own way.

Worst of all, we attempted to rewrite the narrative. We briefly decided that because our results were “better than last year,” that meant that we were winning, even though we were clearly short of our goal. So when we talked about it, we were proud of our day, and proud of the improvement over last year.

But we all knew it…we weren’t winning.

It took until the last moment of our first conference day for someone to say it. But then, thankfully, someone said it: “I’m really disappointed about where we are against our goal right now.”

And little by little, the truth came out — “there’s a part of our product that isn’t resonating with this audience.” “I don’t have a way to show someone what we actually do.” “I’m afraid to strike up a conversation.” “I got discouraged, and then I ran away.”

And right then, sitting around and feeling realllllly tired in our VRBO after a big day of conference (and before an even bigger one), I watched something in our company change. I watched us listen to the hard truth that we weren’t on track to hit our goal, and then I watched us mobilize, re-organize, and make a new plan.

I watched us give and receive feedback — and nobody died or threw up.

I watched us ask “What’s my exact number for tomorrow? I’m ready.”

I watched us say “Let’s go earlier than we said tomorrow, to give ourselves the best chance.”

It was so cool to see it. I had goosebumps. And on Friday, it all clicked.

I watched you wake up and get in front of our customers 5 hours before everyone else, in the most creative, hospitable, totally-us-kinda-way. It was so fun.

I watched you get brave and help each other get brave, too. You helped me!

I watched you teach each other things, and teach me things. Thank you for that.

I watched you make great use of our company’s resources, and then I watched you take risks when you believed there was an outsized reward available to us. (I’ve never purchased more lattes in my life!)

I watched you never take a single moment of the day for granted. THANK YOU.

Your hospitality for our customer was genuine and perfect. Your focus on asking people for the opportunity to work together was hard work, and you did an extraordinary job of getting comfortable and going for it.

And yet — none of that is the transformational part. The thing that was different — that IS different about our company now is that you didn’t do any of this because someone asked you to or said you had to.

Nobody got in the minivan at 5:45 am because it was in your job description. Nobody on our software team booked sales meetings because you were told to. You did it because you figured out what it would take for the company to win, and what part of that you could play, and then you did that thing.

And we won — we started Friday 35% to our goal, and ended the day 102% to goal. We were talking to customers before 7 am, and we were the absolute last team on the floor to shut down the booth, and it paid off. Our calendars are full from start to finish for the foreseeable future. We added more pipeline, booked more demos, and had more meaningful conversations than we ever have in a single day in the company.

At a start-up company where teams are small and resources are limited, taking ownership matters. A team of owners has 10x the impact over a team of employees, no matter the size of the team.

The reward for taking ownership is more time with customers. Because we decided to own our luck and win the day, we got the opportunity for more conversations, with more current and future customers, than ever would have been possible. We owe them our gratitude for that opportunity, and I know we will all show that in the weeks to come.

I cannot wait to see what each of us will own and transform in the weeks to come. I hope you’ll look back on our week and see the kind of impact we have when we say the hard thing, take ownership, and own our future together. I’ve truly, actually, never been more proud of our company — and that’s really saying something.

Gratitude x A Million,

KB

Happy Q1 Retreat Week! Happy NCE Week! WOW this is a big week!

I figured you might want some airplane reading/thinking topics today as we travel, so I wanted to introduce a concept that we’ll be talking about as part of retreat. Tomorrow, we’ll talk about how we’re going to grow as a company this year, and central to that conversation is leadership.

One of my favorite leadership tools I’ve ever learned about is the Leader ReadMe. It’s a simple way to start speaking the same language with leaders in your company, understand the best way to communicate with your manager, and build expectations for your teams.

So what IS a Leader ReadMe? Well, thank you for asking.

First, a History Lesson.

A long long time ago when personal computers were rather new to most of us, many pieces of software were purchased in an actual store (yes and software came in an actual box) which you then installed on your computer. Once installed, you would very often find a simple text file in the software named “README.”

That file contained the operating instructions for the software. How to use it, which commands you’d need, the rules of play for a game. So whether it was business software like Microsoft Excel or a game (Oregon Trail? Anyone?), you’d have a simple way to know how to use the software as soon as you’d installed it.

I promise I’m going somewhere with this, and now you all know JUST how truly old I am.

Years ago, I learned about a leadership practice called the “Leader ReadMe.” The practice originated in the tech industry and was made particularly popular by the then leader of Netflix, back when Netflix still shipped DVDs to people in the actual mail. (Yes, I was around for that too).

Leader ReadMe: An operating guide for working together

The idea of a Leader ReadMe follows the same principle as a software “ReadMe” file, but for leaders and managers. Essentially, it’s a guide to how to work with a leader, setting up expectations and norms from the very beginning. A leader’s ReadMe can evolve and change, and can adapt to the company or team.

A ReadMe It isn’t a sales pitch or a resume but rather a simple set of things to know about working with someone as a leader. What they expects, what they care about, how they works, when they works, and how they help each team member be successful in their role.

At my former company, our Director of Engineering led off his very first day of work by sharing his Leader ReadMe — an operating guide to working for him — with every one of his direct reports. Right from the start, they knew how best to work with him. After reading his, I immediately wrote mine.

Every company and team is different, and my own leadership style has changed with time, so last week while I had the gift of a bit more time on my hands, I took a moment to write a new ReadMe. I now primarily lead other leaders, so mine is oriented in that way, but you can write a Leader ReadMe for any type of team.

You’ll find my Leader ReadMe here in a new space for them on Notion. (If you’re reading this and you aren’t on the Alpaca team, but you want to read my README, email me at karen at getalpaca.com and I’ll happily share it with you).

Why to write a Leader ReadMe

The simple answer is: clear is kind. To spend the time thinking about and writing about how you work, and sharing that with your coworkers is to give your coworkers a gift. It’s also a gift to you as the leader.

If you manage a team and they don’t know that you work best early in the morning or that you live and die by your google calendar, you risk misunderstandings, miscommunication, and a lack of alignment in expectations. But when everyone is on the same page (and it’s literally written down on the page), you can operate with the same understanding, even if you don’t work in exactly the same way.

We are all leaders here. Yes, you!

If you’re wondering how this applies to you if you don’t lead a team at Alpaca, worry not. You can also write a Leader ReadMe about the kind of manager or leader you WANT to become — it may help you identify the skill sets that you need to build or refine in order to earn a leadership role.

Also, don’t forget that there are more ways to be a leader than managing a team. If you lead a product, an office, a team, a key effort, or our culture, you’re a leader. So in a company of our size, we need everyone to be a leader, actually.

As part of our time together as a team this week, we’re going to talk about leadership and how we’ll grow as a team in 2026, and as part of that, we’ll help each person on the team develop the beginnings of your own “ReadMe.” Start thinking about what might go into yours, and do some exercises to help us each write our own this week.

Everyone buckle up — this is going to be a GREAT week together! See you in Nashville!

KB

Here’s my favorite question of the season: “Do you have any New Years Resolutions?”

Thank you for asking! Of course I do.

If you’ve worked with me for more than a week, you know that goals are my love language.

To be precise: setting out to achieve big things with a team of people I care about and respect is my love language. It’s why I run marathons with The Beeps. It’s why I travel to new places with my family. And it’s why I love coming to work with each of you every day.

But New Years Resolutions run the risk of being contrite, or worse, of being over and dead by January 19th. And if we’re going to set the goals, let’s also set ourselves up for success, yes? Yes.

Last week, we spent a great afternoon on our OKRs and goals for the year. So you already know it:

Alpaca’s word of the year is MOMENTUM.

This year is all about taking the big strides we made in 2025, building upon them, and putting that “mass in motion” to achieve the milestones that transform our business.

Alpaca’s milestones have never been more audacious, AND we know they’re within reach. So, how do we do achieve that momentum?

Friends, we achieve it with unglamorous, one-foot-after-the-next, highly-focused, highly intentional EFFORT.

I know. I know. You’re positively brimming with inspiration at the idea that we are going to achieve our goals this year with “highly focused very hard work.” But it is how we’re going to do this.

And we’re going to make it pure joy, because we’re going to do it together.

Coming into the year, I wanted my own personal goals to align to our company goals, since a lot of my hours and days and weeks are centered on Alpaca (as they should be!). So I built myself a little program to make that consistent effort fun, and to celebrate some Little Wins.

I’m sharing here my plan for 2026 — anyone want to join me!?

KB’s 2026 Goal: 💯 Little Wins

My goal is to build greater consistency and mastery across my life by prioritizing repetition of the practices that serve me best. To do that, I’ll accomplish and celebrate things in 100s — because 100 of any good practice (like running or talking to customers or being awake for the sunrise) is enough to either make it a habit or decide it’s not serving me best and let go of it.

How it works

My intention is to design the day and week to accomplish some activities in Work, Wellbeing, and Personal categories, and then celebrate (just a little!) when I hit 100 of one of them!

Will I make it to 100 of all of these things!? No way!

Will I do some of them 200 or 300 times? Yes.

It’s less about how many get done, and more about what I can learn and build from consistent work toward practices that are good for me. The effort toward them will show me which ones are more important, which ones I can achieve, and which ones it’s time to leave behind.

Here are the efforts I’m focusing on to start:

WORK

Goal: Grow customers, revenue, and team by 100% in 2026.

• 100 meetings with education leaders

• 100 handwritten thank you notes

• 100 new customers

• 100 returning customers

• 100 published posts/articles

• 100 investor conversations (current or future)

• 100 team 1:1s

WELLBEING

Goal: Be consistently ready to run a half marathon (healthy, strong, nourished) and run four good ones.

• Hit a 100 day running streak

• Run 100 miles in a month

• 100 days with 100g protein

• 100 breakfasts

• 100 strength workouts

• 100 pre-10 pm bedtimes

PERSONAL

Goal: Enjoy excellent relationships with every member of my family and take care of myself.

• 100 family meals

• 100 sunrises 🌅

• 100 pieces of art made (any size!)

• 100 family individual check-in texts

• 100 books read (Yikes, honestly?)

• 100 NYT crosswords completed

The Rules

A few things I’m doing to help me keep track and stay on track!

• I’ll keep track to see what I can accomplish during the year. When I hit a 100 Milestone, I’ll celebrate it as a “little win.” (Stickers and a bingo card might be part of this equation).

• Any item can be repeated as many times as time allows (for instance, if I ran 100 miles per month in 3 different months, that would count as 3 wins).

• Habits can be added throughout the year if something makes sense. But only add habits that contribute to overall goals and intentions — no vanity metrics here (aka no one is impressed by making 100 spreadsheets unless they help us reach the actual goal).

Early Results

Alright, it’s early, but here are a few things I’ve prioritized in the first 12 days of the year, and how those things are going:

WORK:

• New Customers: 3

• Returning Customers: 2

• Handwritten Thank You Notes: 10

• Investor Conversations: 4

• Team 1:1s: 2

HEALTH:

• Days Run: 12

• Current Running Streak: 42 Days (started in December)

• Breakfasts: Like 2 (it’s so bad!)

• Pre-10pm-Bedtimes: 7

PERSONAL:

• New York Times Crosswords: 8

• Books Read: 3.5

• Sunrises: 8

So, it’s going. It’ll have ups and downs, I know. And I realize that this little system/program/thing I made is a wee bit complex.

But in a way, the system is complex but the goal is not. The goal is not some mountain-top achievement that happens on one day. The goal is to consistently put one foot after the next.

The goal is reps. At bats. And other sports analogies.

In all its unglamorous glory, the goal is simply to stay focused on the work it takes to achieve big things. Because every marathon is accomplished by 100 training runs (right, Mark!?) — it literally has almost nothing to do with race day.

Now Is When I Ask You to Join Me 😬

So Alpaca…what will you do 100 times this year? Want to pick one thing? If you do, I want to hear about it and I want to encourage you along the way and I want to celebrate that win for you when you hit 100.

Because doing something 100 times is worth celebrating, and it’ll be a lot more fun if we celebrate together. Let’s GO, Alpaca — the momentum is building and the wins are ours to earn.

❤️ x 💯,

KB

Before we jump into our BIG new 2026 on Monday, I wanted to take a moment to look back on what made 2025 great, and what we’ve learned.

I think my favorite moment of our entire 2025 was when got on the phone with our customer Eric Filardi after their school signed the contract that took us over our long-held growth goal (you know what it is!). When I talked to Eric, he said this:

“I’m so excited to be part of your growth story. Teaching me how to better listen to my team has been a game changer for my work as an educator and a a leader.”

Meeting big goals is incredible. But meeting them alongside customers, investors, team members, and friends who see what we’re doing and where we’re going? That’s next level good.

2025 was Next Level Good.

So, what changed in 2025? I think this is the year we learned to listen better.

This year at Alpaca, listening showed up in new software, in new ideas for teacher recognition, in thousands of handwritten notes, in stories shared, and in the stories big and small that educators trusted us enough to tell.

I can’t believe how much we’ve learned from listening this year. Shall we take a look? Here are my highlights.

1. The new Alpaca Pulse helped us listen at scale.

This year, educators completed over 30,000 Pulse check-ins, selecting more than 85,000 sentiments to describe how they feel at work.

The two most common feelings they shared? Exhausted — and Committed.

That pairing says everything about the moment education is in — and why tools to both listen and support is the work we’re focused on delivering.

We also launched the Positivity Pulse, a measure of total positivity in a school building at any moment in time. In our first year with that tool, educators showed an average positivity score of 71% — and we’ll keep learning from that measure over time.

2. We asked one new question that helps leaders celebrate in new ways.

Listening to those sentiments has always been key to our work, but this year, we also started asking a simple but key question:

“What’s going well right now?”

We wanted to find the bright spots so leaders could celebrate them better. So far, we’ve collected 31,000+ Bright Spots, and here’s what educators told us what’s keeping them grounded:

• Feeling anchored to purpose

• Leaders who follow through

• Trust to make decisions

• Feedback that leads to real change

• Communities that show up for one another

3. We got better at delivering on what teachers need.

We’ve always asked “What helps the most right now?” but this year, we built better ways to connect those needs to real action. This year, educators told us 28,000+ things they need, so their leaders could understand what support looks like right now. Then, we connected those needs to more than 250 actionable resources, available right in our dashboard.

Here are the top things they said:

• Recognition in staff meetings

• Opportunities to grow and share strategies

• Small, weekly feel-good moments

• Check-ins around impact and goals

• Surprise treats that simply say, “We see you”

4. We had real, in-depth conversations with more than 1,000 school leaders.

This year, we launched the Little Wins Podcast, introducing us to some incredible school leaders doing extraordinary things to build school culture, little by little. I can’t tell you how many times I took my headphones off after a recording and said “You guys have to hear what this principal is doing.”

That happened everywhere — in the Podcast of course, but also at conferences, in sales and partnership conversations, and in the conversations we’ve had with our customers about how they’re using Alpaca and how they’re building culture in real time.

5. We fell in love with 23 educators when we hosted a summer camp for school culture.

You know how I felt about Camp Alpaca!

Our first ever conference/workshop for educators and culture leaders was a BIG experiment, it was so much work for our teams, and it was my favorite two weeks in the company’s history. Not just because of what our educators built (30+ school culture resources!? YES holy moly). Not just because we gained so much insight and feedback into our product, making it an even better launch for the fall. But above all, because listening to what teachers are looking for at work, and watching them take charge and build those creative ideas out to support their fellow teachers everywhere showed us all the genius of the profession.

6. Care You Can Hold: Packs

We cannot NOT mention the celebrations! Through Alpaca’s unique teacher celebration and recognition care packages, we delivered 27,000 Alpaca Packs into schools across the country.

Each one included:

• One of our 23 custom products, designed and built just for educators, BY educators.

• A handwritten thank-you note — 27,000 of them, written and delivered by educators, retired educators, community members, and friends all over.

Packs are simple by design, but powerful in practice. They turn appreciation into something tangible, timely, and human.

Alpaca’s care packages add a moment of celebration to the hard work of teaching, and a little bit of surprise to a school building each month. I love them, because they remind us to have a little fun, while listening to our teams.

7. Greater impact through listening

By year’s end, Alpaca supported more than 14,000 teachers and school staff members, across 120 district partners and 300 schools, 35 states and two countries, all with one simple idea: that when you listen to teachers, the world can change. That happened because of each of your hard work and support.

Thank You

WOW, y’all — we have a lot to be grateful for. Thank you, Alpaca team, for building with care, curiosity, and integrity — even when the work was complex and the path wasn’t obvious (and I was asking for just ONE MORE THING but on the same deadline).

Partners and investors, thank you for believing in Alpaca’s evolution, and for backing a long-term vision rooted in trust and impact.

And to the educators who invite us into their schools, stories, and signals every day: we’re grateful beyond words, but we’re going to keep telling you, in every way we can.

We’re ending the year more clear, more focused, and more committed than ever to helping schools become places where people feel seen, supported, and celebrated.

Onward — and thank you for being part of this journey.

With gratitude,
KB

Have you ever woken up on Thanksgiving Day and realized your work is your dream job?

That’s an extraordinary feeling. I’ve been thinking a lot about the community of people that surrounds our mission and work and how it’s grown this year. Without fail, every single person who touches this company does so with great care for educators and for our work. I wanted to take a moment to acknowledge a few who have become a big part of Alpaca this year.

I’m grateful for our educator team. You build and create such beautiful, fun, and helpful resources for our customers and educators everywhere, and you do it with such joy.

I’m grateful for our investors. I am beyond grateful that you believe in our team, our mission, and our company. Thanks for all of the encouraging notes, all of the good questions, and all of the offers to help us. We couldn’t be doing this without you.

I’m grateful for our Little Wins Leaders community. I have learned so much from school and districts leaders in every single podcast interview. Sharing even one hour with us has helped me build a new understanding of how to grow our company. Your little wins, culture moments, and practices you bring to your schools and district are inspiring. Thanks for helping us learn every day.

I’m grateful for our customers. Every school and district leader that trusts us to help them listen to, support, and celebrate their educators is at the top of my gratitude list. Our customers give us amazing feedback and ideas. You share the impact that Alpaca is making at your schools. And you are simply some of the most thoughtful and delightful humans I know.

I’m grateful for every member of the Alpaca team. It is not lost on me that you are investing your time, talent, and career growth with this little start-up. You roll with the punches when the unexpected shows up (and it always does!). You take extraordinary care of one another, personally and professionally. You are the world’s best hype squad. You’re hilarious. And beyond all of that, you are working your tails off, running through brick walls to see Alpaca succeed. I’m grateful for you every time I walk in the door of our office and see a workplace filled with hard work, creativity, laughter, and true friends.

Our little idea has shifted and grown. It has felt like the wheels are falling off at times, and it has felt like we’re on a rocket ship at others. (I prefer the rocket ship, thank you!) We are only just getting started, and our company has so much to learn, so much to do, and far to go.

But the community of educators, leaders, customers, investors, and team members that surrounds our company is how I know we’re going the right direction. I love it here, because of you.

Thank you, thank you, thank you for giving me my dream job.

KB

I knew I was going to like Molly Cormier the first time she bounced into a fulfillment day at the office and took over the music playlist. Energetic, audacious, and deeply joyful, Molly immediately found her place on the team, and played Broadway soundtracks from day one.

That first day, the Hamilton Original Broadway cast album was her pick. If you know me, you know that Hamilton is my favorite musical. What you might not know is that it’s because that musical changed my life 9 years ago. (Molly, I promise this is a story about you. Roll with me a moment.)

In 2016, I went for a run one morning up in Minnesota. We were there on vacation and I was glad that day to not be at work, because honestly, I was in a job I didn’t love. Nothing wrong with the company or the work — it just wasn’t the right level of challenge or the day-to-day experience I was seeking.

I was looking for a playlist for the run and my brother said “you have to listen to this new Broadway musical. It’s about the life of Alexander Hamilton.” My eyes rolled. This felt like it could only go the direction of a cool-history-lesson-Schoolhouse-Rock type of show and I wasn’t into it. Charlie said “trust me, it’s different.”

So I set off running to the opening song of the show. And about 5 minutes later, I stopped dead in my tracks to figure out what in the heck I was hearing.

Lin Manuel Miranda’s work blew my mind. It was more words than I’d ever heard crammed into a musical. It was energetic and audacious, and deeply joyful. I stood still in the middle of County Road 11, marveling at this thing that an extraordinary team of talented individuals created together.

And that’s when I knew I had to quit my job.

Hamilton made me realize that I wasn’t doing the work that I longed to do. I remember thinking “I only have this one career and life. I need to work with a great team and build something I’m proud of, something that makes impact, something to marvel at.”

So I made a plan, I quit my job 3 months later, and on the day I left, I took my brother to Chicago to see Hamilton on the stage. (We marveled at it.) When I got back, I set out to find the teams that made impact, that created extraordinary work together, and that made us proud.

I’ve ‘been lucky enough to get to do that kind of work every day since then, whether it’s with the companies I joined, the organizations I’m a part of, or Alpaca — the company we’re creating together.

Which is why I knew what to do when, exactly one year ago, a spitfire redhead part-time packout assistant with a penchant for Broadway said to me “I think it’s time for me to stop waitressing at the Cracker Barrel, and I’d like you to take a chance on me in a full time sales role.”

Molly was ready to create something to marvel at.

Molly has never worked in sales, but she was willing to pick up the phone and call 100 strangers every day. She’s the first one in the office every morning, so that she can call the East coast before school starts.

Molly has never been part of a start-up, but she jumped in, and now asks amazing questions and comes up with ideas that continue to shape our work each day. She’s unafraid of feedback and she improves every day because of it.

In just her first year, Molly has instilled our company with energy, audacity, and deep joy, and we’ve watched her grow a lot in the process. She also has a strange magnetism for birds and other wildlife, which is entertaining for all of us.

What I see in Molly is pure potential. Because when you’re willing to raise your hand and ask someone to take a chance on you, and then you’re willing to follow it up with BIG work, big opportunities have a way of showing up.

A team with people like Molly, building something extraordinary together, is exactly the thing I knew was missing from my life the first time I listened to Hamilton 9 years ago. So it’s even more amazing that last weekend, by a stroke of pure serendipity, Molly and I got to see Hamilton in the very same New York theater, on the very same day. And we marveled at it.

Happy FIRST Alpaca anniversary, Molly. Now let’s GO — gotta go, gotta get the job done!

KB

Something crazy happens every time I take a road trip with Kaitlynn Kool.

On a drive delivering packs back in 2022, I learned that Kaitlynn was an accomplished graphic designer. On our drive home from Wisconsin for Fall Retreat, we came up with an idea for Alpaca that led to today’s resource library. And on a very snowy drive through the state of Michigan last year, we built a roadmap for Kaitlynn in sales at Alpaca. It’s a kind of alchemy, the way hunches become ideas and those ideas transform into clear plans and goals.

That drive in Michigan is the one prominent in my mind today, on Kaitlynn’s THIRD anniversary with Alpaca.

It was a drive that required a pickup truck and great focus, owing to the snowstorm that hit us halfway through, and the flight out that evening that required us to get there as quickly as we could.

On that drive, we talked about Kaitlynn’s future at Alpaca. She had just begun trying out sales, and finding some success. But she also had some ideas about email marketing and about social media. And maybe some design.

So, she came to me with an idea for a hybrid role that dabbled in a bit of everything. And I said no.

Perhaps it was the white-knuckled focus required to drive through that snowstorm, but our conversation turned to the topic of focus; of getting really good at the thing you’re doing, and staying relentlessly focused on building mastery in that thing. I asked Kaitlynn to consider going “all in” on learning the craft and practice of sales. To become a student of it, to practice it relentlessly, and to build an early career in it. And you all know what happened next — Kaitlynn didn’t just rise to the occasion, she raised the bar.

In the past year, Kaitlynn has grown into our sales QUEEN. Since she started in sales, Kaitlynn has closed 136 deals, resulting in more than 100 new customers for our company. Her work accounts for more than a third of the total revenue for our company. She has been doing this for ONE year, folks.

Her colleagues describe her this way:

“Kaitlynn takes our customers from being interested in getting to know Alpaca to wanting to be on their school culture journey with Alpaca. She is always up to take on a big challenge and makes it look easy.”

And this, which I couldn’t say any better if I tried:

“Kaitlynn sharpens everything she touches. She listens closely, spots what matters, and is relatable every step of the way. She gives customers a sense of trust and gives our team an incredible image of work ethic and growth mindset.”

I’ve never seen anything like this woman on a mission to be the most extraordinary version of herself. Thanks for building your career here, Kaitlynn — to be a part of your rise makes every one of us better, myself included. I cannot wait to see what we’ll do together in the year ahead.

♥️,

KB

PS: To Kaitlynn’s mom, if you’re reading this: you raised a superstar. Thank you for sending her our way.

“A novice is easily spotted because they do too much. Too many ingredients, too many movements, too much explanation. A master uses the fewest motions required to fulfill their intention.”

— Jiro Ono

I love it when you all bring me little bits of truth and wisdom from the books you’re reading, the podcasts you’re learning from, and the work you’re doing. Last week, a team member dropped this quote into my life after hearing it on The Founders podcast (by the way, this episode is great), and I can’t stop thinking about it. So of course, I went ahead and did a little research.

The quote itself comes from master chef Jiro Ono, and if you haven’t watched the documentary Jiro, Dreams of Sushi, add it to your list. Master chef Jiro Ono’s story of how he has dedicated his life to the craft of sushi making, in a tiny nondescript restaurant in Japan is an absolutely beautiful depiction of the creation of a business, a tradition, and legacy. I didn’t know I could love an entire documentary about sushi, but I did. Because it’s not about sushi — it’s about craftsmanship.

Upon a little further research, I learned that the dedication to simplicity and mastery embodied in the movie, and certainly in that quote, is part of a Japanese concept called shokunin (職人), which literally translates to “a person of their craft.” Shokunin are people who have dedicated their life to their craft, from agriculture to utilitarian folk craft to sushi.1 The practice of this is referred to as shokunin kishitsu (職人気質) or “a craftsman spirit.”

Something here felt so resonant to our work — to the craft of teaching and to profession of education overall. So I kept reading. And what I found is that shokunin kishitsu is built of a few core tenets. I’ve seen these listed different ways, so I’m doing my best here. If you have a great source for this, please let me know! Here they are:

1. Perfection through repetition. Any craft is perfected through doing it over and over and over, sometimes for generations.

2. Moral obligation to the community. That because the craft contributes positively to society, it must be practiced with the utmost respect and integrity.

3. Self-effacement. That the work itself is greater than the person doing it. Operate with humility, in recognition of the work itself.

4. Continuous improvement. There is no finish line, only refinement. The moment someone stops working on their craft is the moment they stop being shokunin.

(OMG I love learning new things so much!) While I was reading — all the work and education parts of my brain lit up with the resonance of our mission and work ahead, and why I believe teaching is such an important profession.

Part of why I have so much respect for the craft of teaching is that to be a teacher is to commit to this craftsman’s spirit. Let’s look at the role of educator against those four tenets:

1. Perfection through repetition? Yes. Educators show up every single morning, often arriving at work in the dark, to start their day. They greet those kids every single morning. They create and refine their work spaces month over month and year over year. They often refine their lessons on the same book or concept or lesson year after year. That consistent repetition makes their students feel safe while continually improving the craft.

2. Community mindset? Of course. It’s why the role never stops at the bell and why educators often fill so many roles — educator, mentor, counselor, advocate, coach, wrangler-of-winter-clothes. Teachers know their craft matters to the collective health of our communities.

3. Self-effacement? Oh buddy! No one knows humility in work more than educators. It’s all I can do to convince some school leaders to come talk about their leadership strategies on the Little Wins podcast, because they insist they’re “not doing anything special.” (Truly, I bet 50% of guests say this to me. Then we find out they're actually school culture geniuses.) Educators are the first to keep the focus on the work, the kids, and their team.

4. Continuous Improvement? Oh yes. “Every day, a little better” is a refrain I hear often with school leaders. And it’s why our veteran teachers (long-standing educators) are so key to school culture — they’ve been refining and practicing their craft with repetition for years, and their work is wiser and more refined because of it.

We have the joy and opportunity to support a profession that defines craftsmanship, and I was so happy to be reminded of that with Jiro Ono’s quote and my little deep dive into this topic.

As you know, I often ask our team to “think like an educator” in our approach to work, and my ask of you this week is to consider the lessons we can learn from this commitment to craftsmanship.

As you’re getting a coffee or preparing for the day, ask yourself these questions:

1. How might I accomplish my work this week with the fewest movements and the simplest path?

2. How might I stay focused on getting better and better and better, not seeking something new, but refining the work in front of me now?

3. How might we lift up the work itself and the celebrate the impact it has on our communities?

If you use these questions, or make a tiny little change in your work this week in this direction, I’d love to hear about it! And if you know more about this topic in general, I’d love for you to share it with me.

It’s the last week of the month,
In an extraordinary year,
With nothing but opportunity ahead of us.

Let’s go, Alpaca!
KB

WOW — what a fun milestone today — our 20th Little Wins Podcast episode is live!

We started this podcast as an experiment, with a goal of connecting to more school and district leaders across the country, building a community of culture-focused educators, and getting the positive narrative of education out into the world. I’m going to be honest here — I wasn’t sure if it would work, if we’d be good at it, or if it was the right move for us as a company. After all, I thought, “it’s not our core business.”

Well, as it turns out — listening to teachers IS our core business.

From Alpaca Pulse to our resource library, to the celebrations we design for schools, it all starts with listening to educators to understand how they’re doing, what’s going well, and what they need.

What I’ve found from every single interview for the podcast is that I learn something new, build new datapoints, understand the role of principal or superintendent more closely, and see new ways to connect the dots.

So! I put together a list of my top lessons from the first 20 episodes. Ready!? Here we go:

Here are twenty lessons these incredible leaders have reminded me.

1. Culture is every choice.

“In a small school, culture isn’t a side project—it’s part of how we do everything.”
— Sarah Harless: Joy is Contagious

Culture isn’t something we manage on Fridays or as part of the Sunshine Committee—it’s woven into every hallway conversation, every smile, every morning greeting.

2. Relationships are the real work

“Our school is a place where people want to be.”
— Jeff Dock, The Win is in the Relationship

Ah! I love this. Imagine what happens when students, staff, and families want to be in your building each and every day. Belonging isn’t a by-product; it’s the heartbeat of a healthy school.

3. Lead with purpose, not position

“So long as I am working in service to other people, I am exactly where I need to be.”
— Gus Carter: Culture isn’t a poster on the wall

The best leaders don’t chase titles—they center themselves in service. I love Gus’s focus on working in service to his teams. It came through in absolutely every part of the interview.

4. Every day is a chance to win with kids

“I look to win the day with kids. It’s more of a mindset than a checklist.”
— Evan Hecker: “Passion shapes the team”

Little celebrations compound. Joy is the most renewable energy source in education.

5. Build trust before systems

“We started what we called Wing Pals… that’s how we built connection again.”
— Alison Canter: Culture that outlasts the leader

People commit to each other before they commit to initiatives. I loved Alison’s example of how she used a simple program to build connection among her staff.

6. Invite families into the story

“We want parents to feel like they can come in and have real conversations with us.”
— Jennifer Rosenbloom: Leading with Purpose and Positivity

Families don’t just visit strong schools—they help build them. Jennifer’s approach to building her new school involves families every step of the way. I can’t wait to see how her school emerges.

7. Recognition rituals fuel joy

“We have a crystal apple the staff selects weekly. It’s our way of saying, ‘We see you.’”
— Samantha Sebestik: Little things make a big difference

A few heartfelt words of recognition can move a whole team forward, and a little ritual goes a long way! I love to hear each of the rituals and traditions our guests have in their buildings.

8. Wellbeing starts with honesty

“We don’t realize how much emotional labor we’re carrying until we stop long enough to breathe.”
— Dr. Luke Beall: Give Teams the Opportunity to Flourish

Sometimes, guests will say things that just floor me! Naming the hard things gives educators permission to rest, reset, and utlimately… stay.

9. Community connection multiplies impact

“The doors are open. We love coming to school—and that makes parents love coming too.”
— Alison Canter: Culture that outlasts the leader

When schools feel like homes, families become partners in culture.

10. Never lose sight of what it means to be a learner.

“I took the Africa geography quiz with students. I went to class, I learned the material, and I took it seriously.”
— Troy Hopkins: “Is there a better way?”

When purpose is clear, the noise quiets.

11. Positivity is contagious

“We have a lot of positive people. It’s kind of contagious.”
— Sheila Taylor: “We Built a Family, Not Just a School”

Positivity isn’t naïve—it’s strategic. Gratitude multiplies the momentum of that positivity!

12. Student voice matters

“Phones away, bell to bell. Once we embraced it, our students started embracing it. Now, we’re seeing the benefits as a school community.”
— Dr. Jessica Sonntag: “Calm, Safe, Enthusiastic.”

I have LOVED hearing the ways that schools and districts engage their students in the work of building their culture. Countless examples — and each of them a repeatable little win. When students help create the environment, they protect it fiercely.

13. Stay connected to why you lead

“I’m coming back to teaching [from being a principal] because I truly believe in what we’re building here. I moved across the country for it.”
— Lindsay Pietrzak: Joy is the strategy

Sustaining culture takes belief—not just in students, but in the mission and the leader. Hearing Lindsay’s story about returning to the classroom was one of my favorite days — and when I got to meet Lindsay’s new principal a couple of weeks later, I GOT IT — great leaders and great cultures can make all the difference.

14. Go to the teams you don’t know!

“My tendency is to hang out with the science department because I love them—but leadership means showing up for everyone.”
— Jeff Dock, The Win is in the Relationship

Jeff illuminated for me a great lesson in going beyond your comfort zone to know and meet the people on your team that you might not have as much in common with.

15. Clear is Kind

“I think Brene Brown said it best: Clear is Kind.”
— Dr. Jeffrey Collier: “We call it Saginawesome.”

Clarity is everything when it comes to feedback, culture, and team dynamics. Jeffrey reminded me how much I love this concept, and SO many other leaders echoed their favorite leadership tips from their favorite books, podcast, and mentors. I have a running list of the books they’re reading, and I’m working my way through it.

16. Communities of leaders creates strength in numbers

“Principals need circles too. You can’t hold all that weight alone—it will crush you.”
— Amber Henderson: You Can’t Pour from an Empty Cup

We all need the communities and circles that build us up. Amber’s lessons on taking care of your self and each other resonated with me deeply.

17. Anchor culture in inclusion

“In our first year, we tried to embed multicultural books in every classroom.”
— Samantha Sebestik: Little things make a big difference

Simple ideas to change culture — it’s what this thing is all about. Representation tells every student, you belong here.

18. Leadership takes curiosity

“One of the things you learn as a building leader is to ask more questions than you answer.”
— Jordan Stuhan: Connection is the Curriculum

YES!! Curiosity opens doors that authority alone never could.

19. Mindset > Checklists

“I look to win the day with kids. It’s more of a mindset than a checklist.”
— Evan Hecker: “Passion shapes the team”

I love the way our guests think less about WHAT they should do and more about HOW they should work. Mindsets over checklists, every day.

20. Love you all.

“I end every email, every announcement, and every chance I get to speak to our school with three words: Love you all. I used to get a lot of pushback for it. But it’s how I feel and I think that matters.”
— Gus Carter: Culture isn’t a poster on the wall

This was the first (and not last) moment in a Little Wins interview when I cried! I loved this story so much, and I think about it every day.

That’s the full list! Please take an opportunity to listen to these amazing leaders — I promise you will learn so much.

I went in to this podcast experiment hoping to better understand our customers. The unexpected result is that I think it’s changing me — in ALL the best ways — as a leader.

LET’S KEEP GOING!

Happy Retreat Time, Alpaca!'

Next week, we’ll spend a couple of days together thinking BIG about Alpaca and our future. Since a few of us are new (or recently returned!), I thought I’d offer a sneak peek of what we’ll be talking about, how to prepare, and how to build a GREAT experience for yourself. (And if you aren’t coming but you read team letter and you’re an investor/ friend/ supporter — hey! Here’s what we’re thinking about as a company right now!)

First, THANK YOU for your input. In my 1:1s with each one of you last week, I heard so much about what you want to learn, talk about, and understand better at retreat. It’s a tall order, because we have a short time! Here’s the game plan:

What We’ll Be Working On: Alpaca’s Next Chapter

My goal in Q4 is to end the year strong and clear, with cadence and focus. For me, that means:

1. We achieve our 2025 revenue goal

2. We have happy, engaged customers

3. We know what the next chapter looks like for Alpaca, and have 2026 goals set

4. We have put into place the practices, work experiences, and team to achieve those goals

That’s how I want to end the year, so that we can hit the ground running on January 1 with some new goals in place! But in order to do that, we’ll need to spend Q4 doing two things: staying incredibly focused on ending the year with great success, and putting time, thought, and work into defining our next chapter. And it starts at retreat!

We’ll be focusing some discussion, ideation, and strategy sessions on how we build a company that’s bigger and more successful than we could imagine, focusing primarily on what’s possible with our software product and how we’ll position and sell that product.

But in addition to envisioning Alpaca’s next chapter, we’ll also focus some time and discussion on how we can each build habits and practices that make our success scalable, reliable, and repeatable. What are the practices that you would like to be habits in our company? Give it a little thought or use it as a topic for your car ride down!

How to Make Retreat GREAT

We each have a role to play in making retreat a great experience for everyone! Here are some things to keep in mind:

1. Ideas over Roles: In these conversations, you are not constrained by the work you do today, but are asked to think about our company as one effort forward. Bring your BEST ideas, feedback, dreams, and willingness to do work for any part of the company — that’s how we build something extraordinary.

2. Bring your “we” mindset: We’re building this company together. Yes, I personally will come with updates, plans, vision, and strategies. But we need each person to bring your best ideas, feedback, and thoughts to this table. If any of us come into retreat with thoughts like “you all in sales should consider doing _____” or “you all building the product could evolve to accomplish ____”, we miss an opportunity to be us. Everything you suggest or comment on or commit to is something we each own a little bit — bring a one-team mindset, and our discussions will go far!

3. Build experiences together: I will NEVER forget cheering Kaitlynn on to get her first bullseye with a bow and arrow in Wisconsin two years ago. I would never have chosen that activity, but she invited me and now, I wouldn’t trade it for anything. Retreat is a GREAT moment to get to know someone a little better. Say yes to trying something new, going for a walk, getting a bit uncomfortable, having a new conversation, connecting with anyone/everyone on the team. When we’re connected we can create great things. Shared experiences are the #1 reason we do retreats!

4. Practice gratitude! We are so lucky to get to spend a day or two together. I’m grateful for your families, your willingness to give up an evening, your excitement and thoughtfulness, all of it. Let’s remember to write thank you notes, show gratitude for our customers, and consider where we can build moments of gratitude and joy around us. It’s our top value and what we’re here to do, and I can’t wait to see how we bring that gratitude forward next week.

Oh and one more thing…

Lightning Talks Are Back!

(Read this one — there’s homework!)

“Do I need to prepare anything?” Thank you for asking!

On Monday night, we will be having our second annual Lightning Talks Happy Hour. The goal here is to simply to get to know each other a little bit, have some fun, and kick off our time together.

So...please prepare a 3 minute talk on the topic of your choosing. Yes, any topic!

Here are the rules:

1. It can be any topic, professional or personal.

2. You may use slides but they are not required.

3. The 3 minute rule will be strictly enforced (but with a cute bell or something!)

4. You may involve the audience in any way you wish but again, 3 minutes.

5. DO NOT overthink this. (In fact last year, everyone had less than 24 hours to prepare!)

Questions? Thoughts? Ideas? Requests? Hit me up! I will be in Alaska at the Principals Conference Friday and Saturday, traveling home on Sunday with LOTS of airplane time. I’d love to hear from you.

Let’s go, Alpaca — see you at retreat!

KB