PEN Profile: Kristen Habacht

We established the Primary Expert Network - a select group of NYC Tech’s leading operators and functional experts - to help us support our portfolio companies through the inevitable challenges of the startup lifecycle. The PEN is such an impressive bunch that we created the PEN Profile Series to introduce them to the community at large, and to provide insights into how these influencers think and lead today’s most exciting startups.

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On the heels of this month’s news of Trello’s acquisition by Atlassian, we’re thrilled to be profiling one of the amazing sales resources in the PEN: Kristen Habacht, VP of Sales at Trello. As the first sales hire at Trello, Kristen’s work ethic, innovative spirit and strategic prowess have paid off handsomely, with Trello now widely regarded as the fastest-growing project management and productivity tool on the market.  Kristen credits much of her success to her direct and honest approach, and we admire the way she’s been able to build an open, collaborative and team-oriented sales force that eschews the competitive, cutthroat mentality of so many organizations.  

From a business standpoint, we, as a firm, are jumping for joy at the Trello news. Known for our bullishness in the NYC enterprise tech scene, this deal is a big SaaS win for our city, and its hefty $425 million price tag is testament to the truly innovative solution the company has built - one that we see in use not only across our portfolio, but in organizations of all shapes and sizes. Trello has become a prime example of how great SaaS products can be grown from the bottom up of enterprise organizations through superior user-experience design and building network effects natively into the product. As Trello continues to grow and develop, we look forward to a future Trello Diaspora that promises to spawn a next generation of winning SaaS products.

@kristenhaba | @trello

Hometown: Atlanta, GA

What brought me to New York: I’ve been in New York for 12 years. I went to college in PA, and moved here when my husband got a job in CT. As an English and Theater major, I’m thrilled with the direction my career has taken!

Why I love the NYC tech scene right now: My first job in New York was at Fog Creek Software (which spun off Trello two-and-a-half years ago). At the time, Fog Creek was one of the first startups here, and it felt a little lonely. Now, there are so many communities and opportunities within NYC Tech, and people are so supportive. It’s been amazing to have witnessed that transformation over the last decade.

Hidden talent: I’ve become known around here for coming up with quirky ice-breakers. On one occasion, our team was kicking off a meeting and I came up with the idea of having the team tell a story by only saying one word at a time. It ended up going in a very weird direction, but it’s became a total bonding moment for our team and an ongoing inside joke.

Last thing I Googled: The train schedule from Connecticut to the city. Turns out, trains do not run on regular schedules on MLK Day.

Biggest challenge I’ve overcome at Trello: The biggest challenge has been figuring out effective sales strategies. Trello’s is not a traditional sale because we’re running a prosumer/freemium model, so a lot of the sales tactics we’d learned and executed in previous jobs had to be tossed aside. Instead, we learned by experimenting and created our own rule book. Part of this challenge also involves finding people for our team who are flexible and creative thinkers who can adapt to a new paradigm, not people who are stuck in the traditional sales models they’re used to.  

Business apps I can’t live without: Trello, obviously, and DocuSign. Also, because we’re a remote company, we rely heavily on Zoom for all of our internal and external calls. I’ve had only positive experiences with Zoom.

What I’m best at: I’m really good at being direct and honest with people. I don’t beat around the bush. This can take some people by surprise, but once they get used to it they realize that I want what’s best for my team and I want my colleagues to succeed.

Thing that drives me most crazy: I am not a professional Googler. If there’s something you can Google and find the answer yourself, just do it.

Proudest accomplishment: I’m really proud of the sales organization I’ve built at Trello. We’ve grown from 0 to 30 people; built out an entire sales model; and developed a clear progression path for our employees. And we did that all while maintaining our values and the vision for the team we initially set out to build - that is, really open, honest, team-based, collaborative and not cutthroat.

How I keep my team engaged: One of the benefits of being at a startup is that every team member we bring on is still helping us build out the product and company in a very hands-on way. Even as we’ve grown, people really feel a sense of ownership in knowing that their suggestions will be seriously considered and often implemented. That spirit keeps everyone engaged and motivated.

My first job: I was a bus girl at a 1950s-themed diner. I started working there when I was 15. My parents would come by to see me working; they made friends with the owner and ultimately wound up buying the place!  

My key mentors: I’ve learned a ton from our CEO Michael Pryor in the way he built Fog Creek and, since then, Trello, and he’s a huge contributor to the NYC Tech scene. Also, my first sales manager, Kathleen Roberge at Perimeter eSecurity (which has since been wrapped up into BAE Systems). At the time, banking was a very male-dominated space. Kathleen was often the only woman in the room, and I think about how good she was at holding her own and successfully running her team. She was very straightforward, and she also did everything she could to make sure everyone on her team was successful. If someone showed they could do more, she pushed them forward. I’ve followed a lot of her examples here.

Other than Trello, NYC Tech company I most admire:StackExchange is doing a lot of cool stuff in terms of how they  run their sales team and develop their culture. For instance, they don’t have sales quotas and they let their reps set their own targets. They’re also very transparent with regard to rep performance, which has resulted in a very collaborative and supportive culture. When we were building our team initially, I looked at StackExchange’s successes and failures and learned a lot from them.