Alex Wakefield is Chief Revenue Officer of AcuityMD, the commercial platform for the med-tech industry, which recently raised $80M at a near-billion-dollar valuation. He joined when the company had fewer than 20 customers and roughly $2M in ARR; today it serves more than 500 customers and has scaled past $50M in ARR. His path to CRO is anything but typical: he began in the Navy's supply corps, moved into global supply-chain and logistics operations at IBM, got pulled into enterprise technology on an early SAP R/3 rollout in the late 1990s, and discovered selling through SPIN — eventually running the Americas business at Model N and leading commercial teams at JDA and Longbow Advantage before stepping into a CEO seat and, ultimately, choosing to return to a CRO role on purpose. His through-line: an operations background is a superpower in sales, because once you see that managing a deal is like managing a project, selling takes on a whole different meaning.
“Before I made the leap, I talked to no fewer than 25 people — fathers and mentors and advisors and CEOs — and said, 'Is this kind of crazy, to do this move from CEO to CRO?'”
“The compensation, equity, and how-you-feel-about-yourself math just kind of makes sense when you're in a good build and a high-growth mode with a great culture.”
“The consistent OKR that I had promoted to the organization that I did not deliver was data completeness and accuracy in CRM.”
“The sooner you can start to measure those things, the better decisions you can make. And I think you'll make fewer mistakes down the line in hiring, enablement, process efficiency.”
“If you have A-player sales reps start leaving, that's pretty noticeable to the outside world. That's not a great thing.”
“I always like to try to mirror and emulate your customer base.”
“Work ethic, passion for an altruistic mission, and believing in what we do is a really interesting common denominator. There's so many things you can teach — those are things that are hard to teach.”
“I definitely want RevOps ultimately to at least have a look at it and a say in it, to make sure it's applicable to multiple parts of the organization.”