For decades, sales trainers have preached the gospel of “get to the decision-maker” or “sell to VITO, the very important top officer.” But does selling to the C-suite really unlock deals the way we’ve been told? On today’s episode, I sit down with Jessica Gilmartin, former CMO and CRO, now board member and advisor, to uncover the truth about executive decision-making. Jessica shares what salespeople misunderstand about the C-suite, why skipping over her team is a huge mistake, and how sellers can actually win executive support the right way.
Meet Jessica Gilmartin
Jessica has led marketing and revenue functions at fast-growing tech companies like Asana and Calendly. With years of experience as a CMO, CRO, and now board member, she’s been on the receiving end of countless sales pitches. Today, she advises companies on go-to-market strategy and knows firsthand how buying decisions really get made at the executive level.
Stop Believing the “C-Suite Myth”
Most sellers think if they can just land a meeting with the C-suite, the deal is theirs. Jessica says that couldn’t be further from the truth.
· Executives don’t manage the day-to-day tech stack or tools their teams use.
· For purchases under ~$50K, the decision almost never makes it to her desk.
· When sellers bypass her team and go directly to her, it creates friction, wastes time, and makes everyone look bad.
Where Decisions Actually Happen
Jessica explains how most buying decisions flow:
1. Team-driven research – Department leaders and managers identify priorities, evaluate vendors, and compare solutions.
2. Executive oversight – CMOs, CROs, or CFOs step in only for large purchases, final budget approvals, or to present to the CEO/board.
3. Headcount limits – Even with budget, implementation resources are scarce. Most companies can only onboard a few tools per quarter, regardless of ROI.
Discovery With Executives? Don’t Do It.
Executives don’t want to sit through basic discovery calls. By the time Jessica is looped in:
· Sellers should already know the pain points and budget from her team.
· Her role is to see a tailored demo, ask a few high-level questions, and give a final yes/no.
“No executive likes to be disco’d. We hate it.” – Jessica Gilmartin
Lessons for Sellers
· Respect the chain of command. Build credibility with the people who will actually use the tool because they’re the ones who influence Jessica’s final decision.
· Ask about budget and priorities early. If it’s not budgeted or prioritized, it’s unlikely to move forward, no matter how flashy your demo is.
· Understand the headcount reality. Implementation capacity is often more limiting than money.
· Tailor your message to priorities. Especially now, AI is top-of-mind for every executive team.
Lessons for Sales Leaders
· Train your team to identify the real decision-making process inside accounts.
· Help reps build business acumen so they don’t embarrass themselves (or their prospects) by pushing too soon to the C-suite.
· Coach reps to champion the “Darrens” inside organizations, the VPs and directors whose recommendations executives rely on.
Resources
· Connect with Jessica Gilmartin on LinkedIn
· Learn more about executive decision-making by joining our Sales Mastermind Class
· Thinking of starting a podcast? Check out Blue Mango...