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

It’s the Cheat Code Christmas Special! Join the hosts for an always colorful, yet never without value, conversation with Craig Rosenberg and Scott Albro on what actually works in go-to-market right now and why most founders are getting it wrong.

If you’re trying to break through buyer apathy, build a brand from scratch, or rethink how you go to market in 2026, this episode will challenge a lot of assumptions. In a world defined by the attention economy, economic uncertainty, and buyer skepticism, Craig and Scott break down why traditional GTM playbooks are failing and what’s replacing them.

The conversation goes deep into why founders, especially technical ones, tend to dismiss go-to-market, how ABM has evolved (and why it’s far from dead), and what differentiated outreach really looks like today. They also explore where AI actually adds value, why productivity gains aren’t enough on their own, and how strong points of view and charismatic leadership can cut through noise in even the most crowded markets.

Chapters

00:00 Introduction and Holiday Cheer

02:59 Understanding Go-To-Market Strategies

06:02 The Attention Economy and Market Dynamics

08:55 Differentiated Marketing Tactics

12:10 Navigating Economic Uncertainty

15:09 Building a Brand in a Crowded Market

18:01 The Role of Founders in Go-To-Market

20:50 Unscalable Tactics for Scalable Success

23:56 The Importance of Brand Recognition

26:23 Understanding Dismissiveness in Founders

28:09 The Role of Charismatic Leadership in Go-to-Market Strategies

30:06 Risk-Taking in Brand Building

32:10 The Evolution of Account-Based Marketing (ABM)

34:44 Leveraging Vertical SaaS for Targeted Marketing

36:10 Innovative Outreach Strategies in Sales

39:01 The Importance of Understanding Your Buyer

41:43 Transforming Sales Teams for Success

44:19 Addressing Buyer Apprehension in SaaS

45:54 Navigating AI in Go-to-Market Strategies

References in the Show:

https://www.forbes.com/sites/forrester/2025/11/05/navigating-2026-key-predictions-for-b2b-leaders/

https://synapticincorporated.com/all/customer-acquisition-strategies-for-2025-the-latest-trends/

Quote of the Show:

"I think the crazy observation for me around what I'm seeing in the market is that buyers are really apprehensive. There's two things that drive that. One, is SaaS over the last 10, 15 years, I think, burned a lot of people with a lot of promises and not a lot of results that they could point to. And it may have put them on the hot seat to a certain extent. Then the other side of it is this massive acceleration of AI that they don't even understand. They can't wrap their head around it.” - Josh Wagner

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

Tune in for a conversation with Kyle Norton, Chief Revenue Officer at Owner.com, on how modern revenue teams are using AI, data, and systems thinking to do more with less. Kyle breaks down how Owner built a highly efficient go-to-market engine by combining deep customer understanding with proprietary data, machine learning models, and relentless operational rigor.

The hosts dig into why today’s CRO must think like a systems engineer, how to evaluate AI tools without chasing silver bullets, and what founders get wrong when they expect AI to fix broken sales motions. They also explore the future of CRMs, agentic workflows, and why disciplined execution, not flashy tools, is the real competitive advantage in an AI-powered sales world.

Chapters

00:00 Introduction to AI in Revenue Generation

03:54 Leveraging Data for Targeting in Vertical SaaS

10:16 Building an Outbound Engine: Strategies and Results

13:13 Attention to Detail: The Key to Sales Efficiency

18:00 The Evolving Role of Sales Leadership

22:04 AI Integration: Balancing Top-Down and Bottom-Up Approaches

24:52 AI in Sales: Understanding Market Dynamics

28:12 Evaluating AI Tools: Testing and Implementation Strategies

32:53 The Future of CRM: Disruption and Integration

39:57 Architecting AI Solutions: Master Agents and Context Management

43:03 Organizational Design for AI: Building Effective Teams

References in the Show:

https://www.revenuebrew.com/stories/2025/10/06/why-cros-are-rising-in-popularity

https://www.hansonsearch.com/articles/sales-marketing-chief-revenue-officer/

Quote of the Show:

"You have to combine art and science. Like you can't just tell a model, hey, tell me what my ICP is. You have to bring nuance to it. And you have to have a very in-depth and intimate understanding of the types of customers that you feel like you can win and serve really well and try to get hyper-targeted with it. And all the AI tools can help tremendously to do that refinement and then eventually do the scraping, enrichment, scoring and targeting. But it all starts with a really clear understanding of ICP.” - Kyle Norton

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