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 — a product and an industry he knew nothing about — was shipped to Texas to open a new territory from zero, and was running the entire sales team by the age of 27, after his boss set one condition on the promotion: he could not leave the rep job until he had replaced himself. He spent more than a decade at Bank of America leading sales and business development for its small business unit, then ran BD at LendingClub as it went public, and 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. His core argument is that selling is a teachable craft rather than a personality type — and that a leader owes every person on the team four things off the elevator: a shared definition of good performance, fair compensation, respectful treatment, and the resources to actually do the job.
“People are going to roll balls to your feet. Just be careful which ones you pick up.”
“And the challenge was, listen, you can't leave this job until you replace yourself.”
“Once I started doing it I got really excited about almost like writing a recipe to be a sales rep.”
“Capitulation, which is inevitably three or six months in the rep would say: I got it, I know how to do this, but I'm just gonna be myself and I'm gonna do what you told me to do and I'm gonna bring myself to the job. And you're like, good, now we're getting somewhere.”
“I really, really believe that you can teach the craft of selling something to people to roughly anybody.”
“It's a great lesson for hiring, because when you're hiring for people, if you're hiring for a personality, you can fall into that trap.”
“Sales is trying to convince somebody to buy something that you genuinely think is going to be good for them.”
“The idea was, when you leave your job, what will your manager say about you? What will your peers, what will your customers say about you?”