Sales Operator Series Ep 7. Mark Kosoglow, Chief Revenue Officer at Docebo

Mark Kosoglow, the sales leader behind Outreach's legendary early GTM culture, joins Brian Trautschold on the Sales Operator Series to break down how fast revenue leadership is changing, and what actually still matters. Mark shares why AI is splitting sellers into two diverging worlds: the "normal people" figuring out prompts as they go, and the "dark arts" technical operators building an edge most reps can't see coming. He explains his framework for project-based vs. people-based work, why AI is opening external influence to people who could never sell before, and why real sales chops matter more than ever in a world of infinite options. Then he goes deep on leadership: the trust-driven culture that had 25–30 reps in the Outreach office by 6 AM, why the "bad manager" who drives reps out of a company usually isn't the real problem, how AI-driven coaching can rebuild rep–manager trust, and why your best rep might make a terrible manager (and might not even want the job). Finally, Mark reveals the first thing he fixes in any new org (process, always) plus "10 Labs," the program he runs to give his top 35 GTM performers direct access to the CFO, CPO, and CEO, and how it builds the "canaries in the coal mine" every leader needs. What you'll learn: The two diverging worlds of AI adoption in sales, and which side wins Project-based vs. people-based work, and how AI blurs the line How Mark built the high-trust, high-energy culture at Outreach The real reason reps quit "bad managers" (hint: it starts with the rep) Using AI to spot coaching gaps managers used to miss entirely Why great reps often shouldn't become managers Why process beats everything when Mark joins a new org Inside "10 Labs": giving top performers a direct line to the exec team Chapters: 00:00 – Intro: a friendship since 2015 02:08 – The two diverging worlds of AI in sales 05:30 – Project-based vs. people-based work 08:37 – The consumerification of B2B buying 10:48 – Why human selling skills matter more than ever 12:08 – Building the legendary Outreach culture 17:00 – Merging great people leadership with AI automation 17:23 – Hot take: why reps (not managers) break trust first 19:50 – Best rep ≠ best manager 23:43 – Where Mark starts in every new org: process 26:39 – Inside "10 Labs" and building canaries in the coal mine 30:07 – Where to find Mark Connect with Mark: Find him on LinkedIn. He posts a few times a week and responds to DMs.  / mkosoglow   #Sales #SalesLeadership #RevOps #AI #GTM #SalesCoaching #B2BSales