Hiring marketing talent is one of the biggest blind spots for early-stage founders, and Jessica Gilmartin has seen the same mistakes play out over and over again.

In this episode, Jessica (former CMO/CRO at Calendly) shares why “marketing” is actually multiple jobs, how to decide whether you need demand gen, product marketing, or brand, and why most founders hire the right person for the wrong stage. She shares real frameworks for setting clear expectations, building trust through communication, and avoiding the toxic ripple effects of a bad hire.

The conversation also covers what the best early marketing leaders have in common (including the underrated value of entrepreneurial experience), why duct-tape marketing eventually collapses at scale, and why marketing needs a real seat at the executive table… not tucked under sales.

Chapters

00:00 Introduction and Guest Background

02:53 The Challenge of Hiring Marketing Talent

04:04 Understanding Marketing Roles

05:44 Evaluating Marketing Needs

07:40 The Importance of Experience in Marketing

10:48 Hiring for the Right Stage

12:55 Setting Expectations and Goals

22:29 Red Flags in Hiring

24:46 Communication and Trust in Marketing

30:09 The Distinction Between CMO and CRO

34:12 The Importance of Marketing at the Executive Table

References in the Show:

https://www.entrepreneur.com/starting-a-business/the-5-mistakes-that-kill-startups/499868

https://hbr.org/podcast/2024/10/why-founders-need-to-focus-more-on-sales-and-marketing

https://www.linkedin.com/pulse/12-most-common-mistakes-made-building-your-first-sales-lemkin-ucw7c/

Quote of the Show:

"I've never been sad that I have fired too early. I've only been upset with myself if I have fired too late. I think a bad hire or a bad employee is absolutely toxic to everybody else in the organization.” - Jessica Gilmartin

Ways to Tune In:

• Spotify: https://open.spotify.com/show/5GpM8myxsUinc5bfLIbjJz?si=0af576adfb8e49f8
• Apple Podcasts: https://podcasts.apple.com/us/podcast/the-cheat-code/id1692445190
• Amazon Music: https://music.amazon.com/podcasts/cb0b3afa-063f-4f3b-96be-b98214c74912
• YouTube: https://www.youtube.com/@CheatCodePodcast