Around the table: Over the past few months, I’ve really enjoyed hosting a new series of small-group roundtables with CROs and CMOs who are part of our memoryBlue Inner Circle. These sessions are open, candid and focused on one big challenge at a time… the kind that shapes modern revenue leadership.
Our first discussion zeroed in on a classic scaling dilemma: how to hire a VP of sales who truly fits the stage you’re in.
It’s a topic that ties directly to a recent blog from Richard Fifield, our chairman, on what organizations look like at every stage of growth. His piece makes an important point: structure and scale go hand in hand. You can’t hire a VP who’s used to flying a 747 and expect them to thrive while you’re still building the runway. (Read Richard’s post.)
Grit over glamour: Right-sizing leadership hires based on where your organization was our starting theme. For example, during the early stages of a company, there’s a seductive logic to hiring someone who’s “done it at scale.” Big brand, big title, big numbers. But the stories that ended well in our Inner Circle roundtable had a different pattern.
They started with someone who understood the specific mess your stage brings: thin brand, inconsistent pipeline and a CRM held together by duct tape… and who got to work immediately.
As Dan Panesar, CRO at Certes, put it: “No one writes that they’re rubbish.” He doesn’t start with CVs. He probes for stage-fit: same chaos, same resource constraints. “I want to hear how you diagnosed real problems, built from scratch, and got back up in an hour when things went sideways.” His filter? Bounce-back-ability and the willingness to build playbooks without brand air cover.
Forecasting reality: Early in a new VP’s tenure, forecasting misses happen because optimism outruns rigor. “People are like puppies. They get excited about the deal,” one participant said.
That’s why methodology and discipline have to arrive fast: MEDDIC or MEDPIC to enforce discovery quality, exit criteria to prevent stage inflation, and weighted forecasts to keep optimism honest. Some leaders are even layering in AI-assisted deal velocity, not to replace judgment, but to illuminate it: who’s really engaged, who’s gone dark, where the last meaningful touch happened.
Context beats credentials: Compensation came up too, and it’s another example of why reflexes must match stage. Designing plans that reward long-term, value-anchored selling without torching cash is hard. Get it wrong and you either burn runway or teach the wrong behavior.
The best VPs navigate those trade-offs clearly… with finance…not against it.
Bottom line
The right VP of sales for your stage won’t always have the flashiest résumé. Look for grit over glamour: the builder who thrives in ambiguity, installs discipline quickly, and lifts the team’s performance measurably.
