Reachdesk Co-Founder & CRO, Alex Olley, on the brutal investor grilling that exposed his gaps as a CRO, and the coaching relationship that rebuilt how he leads revenue, from operational rigour to AI-powered selling.
What happens when the investor everyone expects to say ‘yes’ tears your Go-To-Market plan apart in front of 15 people?
For Alex Olley, Co-Founder and CRO of Reachdesk, that moment at his Series B in 2021 became the inflexion point of his career as a Revenue Leader.
In this episode, Alex tells us the full story from that shocking investor meeting to the coaching relationship that changed his career and Reachdesk forever. We also touch on how Alex is deploying AI today - from surfacing high-intent accounts to using outbound and business cases and why he believes efficiency without accuracy is a trap.
It's a conversation about the line between the art and the science of selling, and what it actually takes to go from good to great as a CRO.
📚 Episode Chapters
04:00 - The Series B wake-up call
13:00 - Lessons on Sales Rigour
23:30 - Art vs Science in Sales
25:00 - Applying AI without losing creativity
29:00 - The importance of unit economics for CROs
🎧 Continue listening…
Make sure you listen to Season 2 with Sam Jacobs on building for efficient growth