Sales Hacker

JULY 8, 2025

06:33 Why Sales Nav was a $250M business with a “crappy product” — and how Doug turned it around. 13:26 The speed dating hack that landed Coffee’s first sales leader. 17:36 What Doug learned running Sales Cloud at Salesforce — and why he left. 24:37 Why sales tech stacks are bloated — and how AI-native CRMs solve it.

Sales Recruiting

SaaStr

JULY 5, 2019

But I started to learn what it took to recruit, inspire, and yes fail a team. Luckily, she worked in the same company and had co-invented the technology. And I learned to recruit. To hire our CTO, our first VPE, etc. And to close $6m in customer contracts through founder-led sales. I’m still learning.

Part-Time VPE

Outseta

MAY 8, 2020

The world of technology start-ups has been good to me—it’s provided for my family, it’s given me a wonderful amount of freedom to live my best life outside of work, and it’s been intellectually engaging and challenging throughout. Today I can look back across a full decade that’s been spent building SaaS start-ups.

Part-Time VPE