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Here is a list of Content & 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