Cracking Outbound Why Curiosity, Not Cold Calls, Drives Pipeline Today with Harry Monkhouse
Harry Monkhouse runs global outbound at LastPass, where most people still know them as a password manager. But with 35M+ users and a brand-new B2B product, his team is building a pipeline from scratch, without a strong outbound history to lean on.
In this episode, Harry breaks down how he’s using trigger-based plays, website signals, and old-school cold calls to drive meetings. We talk about why he left AE life to return to SDR leadership, what he learned from 6sense and Terminus, and why AI agents will change the game way sooner than most people think.
If you care about pipeline, hiring, or where outbound is headed, this one’s worth your time.
In this episode, you’ll learn:
- Why AI agents might replace parts of the BDR role in 3 years and what to do about it now
- How to run outbound with a massive B2C user base and minimal historical motion
- Why the best reps and managers focus on trigger-based selling and consistent playbooks
Things to listen for:
(00:00) Introduction
(01:19) Why outbound leaders should think more like operators
(02:32) Lessons from working at 6sense and Terminus
(04:58) Trigger-based outbound plays that still work in 2025
(06:38) How stepping back into BDR leadership changed Harry’s career
(09:13) The one skill Harry hires across every region
(11:40) What AI is already doing well in outbound
(13:25) How reps should think about AI agents in the near future
(15:32) What selling looks like at a company with 35M B2C users
(18:19) Turning personal users into a B2B pipeline
(20:06) Using BDRs to drive customer expansion—not just net new
(22:28) Coaching reps to work both expansion and outbound motions
(24:41) The case for warmth: why outbound doesn’t have to be cold
(25:57) Where Harry sees the next big outbound opportunity
(27:44) Why most companies promote the wrong people into BDR leadership