What are the key takeaways from this The Sales Evangelist episode?

Key insights include: **Decision Authority Reality:** C-suite executives rarely make tool purchasing decisions directly. CMOs and CROs at companies with $50M+ revenue delegate budget and decision-making power to team leads who understand technical requirements, integrations, and day-to-day implementation needs far better than executives do.; **Going Over Heads Backfires:** Contacting executives after speaking with their team members creates embarrassment for everyone involved. The executive forwards the message to their team member asking why the salesperson went around them, damaging trust and making the vendor look desperate and unprofessional in the process.; **Implementation Bottleneck:** Budget is not the primary constraint for technology purchases. Companies can only implement two to four new tools per quarter because they have just one or two people handling all implementations, plus every tool must pass through security, privacy, legal, and finance review processes.

What did Jessica Gilmartin discuss on The Sales Evangelist?

Jessica Gilmartin, former CRO at Calendly and CMO at multiple companies, reveals why traditional executive selling strategies fail and explains how C-suite buying decisions actually work in 2025. Key topics include: **Decision Authority Reality:** C-suite executives rarely make tool purchasing decisions directly. CMOs and CROs at companies with $50M+ revenue delegate budget and decision-making power to team leads who understand technical requirements, integrations, and day-to-day implementation needs far better than executives do.; **Going Over Heads Backfires:** Contacting executives after speaking with their team members creates embarrassment for everyone involved. The executive forwards the message to their team member asking why the salesperson went around them, damaging trust and making the vendor look desperate and unprofessional in the process..

How long is this episode of The Sales Evangelist?

This episode is 34 minutes long. SignalCast provides an AI-generated summary so you can get the key insights in about 3 minutes.

The Sales Evangelist

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

September 1, 2025

34 min episode · 2 min read

Jessica Gilmartin

Episode

34 min

Read time

2 min

Topics

Investing, Fundraising & VC, Leadership

AI-Generated Summary

Published Dec 25, 2025

Key Takeaways

✓Decision Authority Reality: C-suite executives rarely make tool purchasing decisions directly. CMOs and CROs at companies with $50M+ revenue delegate budget and decision-making power to team leads who understand technical requirements, integrations, and day-to-day implementation needs far better than executives do.
✓Going Over Heads Backfires: Contacting executives after speaking with their team members creates embarrassment for everyone involved. The executive forwards the message to their team member asking why the salesperson went around them, damaging trust and making the vendor look desperate and unprofessional in the process.
✓Implementation Bottleneck: Budget is not the primary constraint for technology purchases. Companies can only implement two to four new tools per quarter because they have just one or two people handling all implementations, plus every tool must pass through security, privacy, legal, and finance review processes.
✓AI Budget Exception: Every company maintains a separate AI budget even when freezing other spending. Expect short-term contracts, proof-of-concept requests, and simultaneous evaluation of three to four competing AI tools as organizations test solutions without clear success blueprints or established evaluation criteria.

What It Covers

Jessica Gilmartin, former CRO at Calendly and CMO at multiple companies, reveals why traditional executive selling strategies fail and explains how C-suite buying decisions actually work in 2025.

Key Questions Answered

•Decision Authority Reality: C-suite executives rarely make tool purchasing decisions directly. CMOs and CROs at companies with $50M+ revenue delegate budget and decision-making power to team leads who understand technical requirements, integrations, and day-to-day implementation needs far better than executives do.
•Going Over Heads Backfires: Contacting executives after speaking with their team members creates embarrassment for everyone involved. The executive forwards the message to their team member asking why the salesperson went around them, damaging trust and making the vendor look desperate and unprofessional in the process.
•Implementation Bottleneck: Budget is not the primary constraint for technology purchases. Companies can only implement two to four new tools per quarter because they have just one or two people handling all implementations, plus every tool must pass through security, privacy, legal, and finance review processes.
•AI Budget Exception: Every company maintains a separate AI budget even when freezing other spending. Expect short-term contracts, proof-of-concept requests, and simultaneous evaluation of three to four competing AI tools as organizations test solutions without clear success blueprints or established evaluation criteria.

Notable Moment

Gilmartin admits she has no idea what her marketing team's tech stack or data infrastructure looks like, cannot answer questions about reporting tools, and would be murdered in her sleep if she mandated specific technology choices without understanding integration requirements.

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Episode Transcript

This episode is brought to you in part by the following TSC sponsors. It takes a lot to grow your business, a lot of audience attraction, a lot of lead scoring, and all the channel managing you can manage. Plus, a lot of long days, late nights, and weekends, a lot of wishing there was an easier way. But with Breeze, HubSpot new collection of AI tool, it's easier than ever for marketers to attract audiences, increase leads and score customers fast, which means pretty soon your company will have a lot to celebrate. Visit hubspot.com/marketers to learn more. This episode is brought to you in part by Blue Mango Studios. Imagine using a podcast as a lead generation source, not only attracting your ideal customer, but entertaining them and getting qualified leads. To find out more, go to bluemangostudios.com. If you're struggling to close deals, you need to try LinkedIn Sales Navigator. Get a sixty day free trial all on the house. Go to linkedin.com/tse. Again, linkedin.com for a sixty day free trial of LinkedIn Sales Navigator. Everyone wants to sell to the c suite, but almost everyone is doing it wrong. Here's the truth about what executives actually want in 2025. Check it out. Hey. Hey. Hey, everyone. Welcome to another great episode of the Sales Evangelist Podcast. I'm your host, Donald c Kelly, the sales evangelist. And I'm so excited for another great episode. I'm so excited to be here with you today. And on this episode, I have a powerhouse guest, one of my favorite episodes all year so far. This is Jessica Kilmartin, and here's why I am a big fan of Jessica and why you should be as well. So let me just give you a background. Jessica not she only has a cool name. That's my sister's name as well. Jessica was the the chief revenue officer and the CMO at Calendly. Jessica was the head of revenue at Asana. Jessica was the chief marketing officer at Honor. And Jessica right now works on and sits on several different boards in boardrooms when it comes towards helping teams of many different size, these executives, to be able to make decision. She knows what it is that executives want. And in this episode, we break down some of the simple like, some of the most annoying things that we do, and I'm gonna confess that I've done some of these things thinking that this was the right thing. But executives are telling us what we should do to sell to them nowadays. The games change. And if you follow these things, I personally know you're gonna see a difference because it's what they're sharing, and it's what my experience have led me to believe and to come to know. If this is your first time listening to our podcast, you better subscribe because I'm gonna tell you every single time we go and drop a GM like this, you're gonna love it. If you …

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