November 8, 2025

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.

Team Letter

All hail the QUEEN.