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.
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