Cracking the C-Suite Code: What Executives Really Care About in 2025 | Jessica Gilmartin - 1929

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Sep 1, 2025

In this engaging conversation, Jessica Gilmartin, Chief Revenue Officer at Calendly and former Head of Revenue at Asana, shares her insights into C-suite dynamics. She tackles common misconceptions about selling to executives, emphasizing the need for targeting the right team members. Gilmartin discusses the importance of understanding financial priorities and the role of technology in sales strategies. She also delves into the RFP process and the integration of AI, highlighting the challenges executives face in balancing expectations with practical implementations.

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INSIGHT

Executives Aren't Tool-Level Experts

CMOs and other C‑suite leaders cannot know every tool their teams use across 40–100 platforms.
Expect decisions to be driven by team experts, not by C‑suite micromanagement.

ADVICE

Verify Budget And Priority First

Confirm who owns the budget and priorities before escalating to the CMO or CRO.
Ask if the purchase is budgeted and prioritized to avoid wasting executive time.

ADVICE

Respect The Team Relationship

Never bypass a trusted team member by emailing the C‑suite without permission.
Instead, ask discovery questions about the internal process and who is informed.

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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 Studios

Sponsorship Offers

1. This episode is brought to you in part by Hubspot.

With HubSpot sales hubs, your data tools and teams join a single platform to close deals and turn prospects into pipelines. Try it for yourself at hubspot.com/sales.

2. This episode is brought to you in part by LinkedIn.

Are you tired of prospective clients not responding to your emails? Sign up for a free 60-day trial of LinkedIn Sales Navigator at linkedin.com/tse.

3. This episode is brought to you in part by the TSE Sales Foundation.

Improve your connection on LinkedIn and land three or five appointments with our LinkedIn prospecting course. Go to the salesevangelist.com/linkedin.

Credits

As one of our podcast listeners, we value your opinion and always want to improve the quality of our show. Complete our two-minute survey here: thesalesevangelist.com/survey . We’d love for you to join us for our next episodes by tuning in on Apple Podcast, Google Podcast, Stitcher, or Spotify. Audio provided by Free SFX, Soundstripe, and Bensound. Other songs used in the episodes are as follows: The Organ Grinder written by Bradley Jay Hill, performed by Bright Seed, and Produced by Brightseed and Hill.