Jessica Johnston-Myers has one question for you: Do you want to win?
Alpaca welcomes our new sales leader to the team, and she's here to win.
March 9, 2026
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