The LeanScale Podcast with Anthony Enrico
You Can't Get Promoted Until You Replace Yourself | Cole Gillespie, CRO at Branch
Cole Gillespie's boss told him he could have the sales leadership job — right after he replaced himself. So he sat down and tried to write out what he actually did all day. He expected to find charisma. He found a recipe. Cole is the Chief Revenue Officer at Branch, the workforce payments platform. He started out selling commercial loans to dentists, opened a Texas territory from zero, and was running the sales team by 27. He spent more than a decade leading sales and BD for Bank of America's small business unit, ran BD at LendingClub as it went public, and took Beam Benefits from under $10M to $120M in revenue as CRO. He has guest lectured at MIT Sloan and still teaches Ohio State sales majors, because he thinks every college should have a sales program. In this conversation with LeanScale co-founder Anthony Enrico, Cole makes the case that sales is a teachable craft — and gets specific about what that means for the people you manage. The three-hour callback SLA. The career obituary. Why the leader who has to be asked for the raise already lost. And the lesson he wishes someone had told him at 30: once your basic needs are met, every promotion stops being a step and starts being a trade. WHAT YOU'LL LEARN How to replace yourself on paper — the exercise that turns a top rep into a repeatable playbook CHAPTERS 00:00 — Cold open + intro 01:52 — "You can't leave this job until you replace yourself" 03:12 — Writing the recipe for a sales rep 05:16 — How much of sales is process versus personality 05:44 — Capitulation: when a rep stops copying and starts owning 08:08 — The trap of hiring for personality 14:33 — The career obituary 18:00 — Turning "responsive" into a three-hour SLA 21:36 — The four things you should expect off the elevator 25:01 — OKRs at the VP level, activity at the rep level 29:36 — Paying fairly when your best rep joined at the bottom of the band 36:39 — The raise nobody asked for 42:10 — Resourcing the job — the fourth thing, and the one leaders skip 49:30 — Respect, friction, and the "no assholes policy" problem 57:18 — Dad Wisdom 1:00:09 — When a career stops being survival and becomes a choice 1:04:00 — The cocktail: comp, title, industry, people, impact 1:12:00 — "Why do you want to be a CRO?" 1:13:39 — Wrap ABOUT THE GUEST Cole Gillespie is the Chief Revenue Officer at Branch, the workforce payments platform powering fast, flexible pay for W-2 and 1099 workforces. He started out selling commercial loans to dentists, opened a Texas territory from zero, and was running the sales team by 27. He spent more than a decade at Bank of America leading sales and BD for its small business unit, then ran BD at LendingClub as it went public. He later served as CRO at Beam Benefits, helping take it from under $10M to $120M in revenue. He has guest lectured at MIT Sloan and still teaches sales majors at Ohio State, because he believes every college should have a sales program. ABOUT THE LEANSCALE PODCAST The LeanScale Podcast is the show for GTM operators building the next generation of revenue infrastructure. Hosted by Anthony Enrico, co-founder of LeanScale, we go deep with the operators, founders, and executives shaping how modern go-to-market teams are designed, scaled, and led. ▶ Subscribe for new episodes ▶ Learn more about LeanScale: https://www.leanscale.team ▶ Follow Anthony on LinkedIn ▶ Follow Cole on LinkedIn KEYWORDS / TAGS Sales Leadership, Sales Management, Chief Revenue Officer, CRO, RevOps, GTM, Sales Enablement, Sales Playbook, Sales Coaching, Sales Hiring, Sales Compensation, People Management, B2B SaaS, Fintech, Workforce Payments, Branch, Beam Benefits, MIT Sloan, Ohio State, LeanScale, Anthony Enrico, Cole Gillespie HASHTAGS #SalesLeadership #RevOps #GTM #CRO #SalesManagement #SalesEnablement #SalesCompensation #B2BSaaS #Fintech #Leadership #PeopleManagement #SalesCoaching #CareerAdvice #LeanScale #LeanScalePodcast
