An Interview With Trello’s VP Sales, Kristen Habacht
Behind every great company, there’s a great sales team and behind every sales team, there’s a great sales leader. Last month I had the opportunity to talk to Kristen Habacht, VP Sales at Trello.
The interview was recorded in the last week of December 2016, just days before Atlassian announced they were acquiring Trello for a whooping $425 million. During our conversation Kristen describes what the Sales team at Trello looks like and how that has changed during the two and a half years since she’s been there. We also discuss their sales compensation, their recent growth and future plans as well as the challenges and opportunities they have faced selling a freemium product.
Content and Timings:
- 0:54–4:20 — Kristen talks about her sales career, how she met Joel Spolsky & Michael Pryor, the FogCreek days and how she eventually ended up as VP Sales at Trello
- 5:00–6:50 — Selling Trello in the early days and how the pitch has changed
- 7:20–12:10 — Kristen talks about Trello’s sales team, their culture, the importance of team cohesion, how they are structured and why
- 12:10–18: 50 — The evolution of Trello’s sales team — how and why the team transitioned from a “full-stack” sales model to role specialisation, and how that helped with scaling
- 18:53–21:00 — Kristen talks about “experiments” that did not work and lessons learned
- 21:00–22:45 — The importance of Sales Ops
- 23:00–24:15 — Kristen talks about recent growth and projections for the future
- 24:25–27:35 — Trello’s commission structure — from, simple to simpler — and why Kristen changed their initial commission structure
- 27:40–34:40 — The challenges of selling freemium products — why traditional qualification models such as BANT don’t work, what can reps do to create urgency and why there’s no sales “playbook” at Trello
- 34:50–38:45 — SMB vs Enterprise sales at Trello — sales cycle duration and how the process differs
- 39:00–42:15 — The challenges of managing a remote sales team and tips, and tools to make it work
- 42:15–45:00 — Lessons learned at Trello & Kristen’s best sales advice — the importance of being able to walk away
