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

Join the hosts for a conversation with Jon Miller, co-founder of Marketo and one of the most influential minds in modern marketing, on how AI, tactic fatigue, and buyer anonymity are forcing marketers to evolve faster than ever. Together they explore the cracks forming in legacy marketing automation and the rise of signal-based journeys. Jon breaks down why the next decade of marketing won’t look anything like the last.

This episode explains why marketers must shift from tactics to context, how AI can streamline operations without sacrificing creativity, and why sales and marketing alignment is still so painfully hard (and what might finally fix it). Jon also digs into the innovator’s dilemma facing big MarTech vendors, the resurgence of niche vertical plays, and the new skills marketers will need to thrive.

If you’ve ever felt like your marketing is losing its edge, this episode will redefine how you think about innovation, AI, and the future of go-to-market.

Chapters

00:00 Thanksgiving Reflections and Family Dynamics

02:59 The Evolution of Marketing Technology

06:01 The Impact of AI on Marketing Strategies

09:06 Tactic Fatigue and the Tragedy of the Commons

11:59 The Role of Specialization in Marketing

15:00 Training AI: The New Marketing Operations

19:59 Future of Marketing Jobs and Operations

20:34 The Role of AI in Marketing Operations

23:08 Evolving Skills in Marketing Operations

24:52 Sales and Marketing Alignment Challenges

27:05 Leveraging AI for Content Creation

30:19 Insights from Market Mapping

31:41 The Future of AI in B2B Marketing

34:27 Innovator's Dilemma in MarTech

39:22 Pricing Innovations in the AI Era

42:09 Personalizing Buyer Journeys with AI

References in the Show:

https://chiefmartec.com/2025/05/beyond-ai-assistants-how-ai-is-being-more-deeply-embedded-in-marketing-and-martech-stacks/

https://martech.org/the-three-forces-that-shaped-martech-in-2025/

Quote of the Show:

"Can your average field marketer now come along and just say, hey, AI, go make me a new webinar for this audience and for this segment? And it actually does it the right way.” - Jon Miller

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

If you’ve ever underestimated the power of hiring, this episode will change the way you think about growth.

Join the hosts for a conversation with Dr. Heidi Ojha, Founder and CEO of Aware Health, on how no-nonsense hiring can make or break your growth story. From identifying organizational gaps to building scalable hiring processes, Heidi shares what it takes to grow a team in one of the toughest sectors: healthcare. She explains why founders should approach hiring like a marketing campaign, the traits that define true high performers, and how onboarding and culture influence long-term success.

Listen in as they discuss startup realities, flexibility, career pathing, and why founders should spend nearly half their time recruiting.

Chapters

00:00 Introduction and Energy Check

01:57 The Importance of Hiring in Growth

06:10 Identifying Gaps and Roles

09:51 Hiring for Clinical and Non-Clinical Roles

13:56 Qualities of High Performers

17:53 The Hiring Process as a Marketing Campaign

21:52 Onboarding and Setting Up for Success

23:24 Revamping Onboarding Processes

27:15 The Importance of Team Integration

30:31 Flexibility in Roles and Responsibilities

32:45 Career Pathing and Growth Opportunities

39:11 Vision and Future Planning in Startups

References in the Show:

https://www.forbes.com/advisor/business/recruitment-strategies/

https://vettio.com/blog/startup-hiring-practices-the-ultimate-guide-for-founders/

Quote of the Show:

"If they're lukewarm in the beginning, that's probably not a good recipe for them working out and being a really strong team fit. So, I think it's a bummer sometimes because I'm like, oh my gosh, this is a perfect candidate, and they're like, eh. So I'm like, nope, I'm going to be eh and pass on them because I want somebody who's like, this is what I want to do with my life.” - Dr. Heidi Ojha

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 the man, the myth, the legend, Bill Binch, Operating Partner at Battery Ventures and former sales executive at Marketo, on what it really takes to build high-performing sales teams in today’s AI-driven world.

From hiring for the right sales mindset to building customer-focused teams and scalable sales processes, Bill shares hard-earned lessons from decades of leading and advising top SaaS companies. He breaks down how founders can make smarter sales hires, why continuous learning separates great leaders from the rest, and how AI is reshaping the future of selling.

Chapters

00:00 Introduction and Overview of the Conversation

03:05 A Day in the Life of an Operating Partner

05:57 Sales Hiring Challenges and Strategies

11:37 Identifying the Right Sales DNA

17:50 The Importance of Value Selling

23:52 Building a Sales Process in Early-Stage Companies

29:47 Adapting to AI in Sales

35:42 Success Signals for New Sales Hires

41:37 Navigating Stale Deals and Customer Relationships

References in the Show:

https://www.businessinsider.com/microsoft-layoffs-salespeople-relationship-guy-ai-solution-engineer-investor-2025-7

https://hbr.org/2025/09/how-successful-sales-teams-are-embracing-agentic-ai

Quote of the Show:

"I wish I could write the one-size-fits-all book on your first sales hire or your first five sales hires and what order they should be. Should it be a sales rep? Should it be a sales leader? Should you have sales engineers? What should you have? What shouldn't you have? But I don't think that exists because it really depends on a number of different factors.” - Bill Binch

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

The world of sales is changing fast and the playbooks that fueled growth a few years ago aren’t enough anymore.

In this special hosts-only episode, Justin, Josh and Sean break down what today’s shifting startup and sales environment really means for go-to-market teams. From evolving buyer expectations to the rise of AI-driven strategies, they explore how top performers are adapting to meet customers where they are and where they’re going next. You’ll hear insights on the new role of full-cycle AEs, why post-sale engagement is the key to long-term growth, and how marketing and thought leadership can drive meaningful differentiation in a crowded market.

They also zoom out with an investor’s view of the market: why Series B and C rounds are getting squeezed, how bridge-to-profitability funding is on the rise, and where private equity rollups in verticals are reshaping go-to-market. Tune in to get an inside look at their perspectives and how modern sales leaders are redefining growth in a more complex, connected, and customer-centric world.

Chapters

00:00 Introduction and Market Landscape Overview

02:47 Startup Growth and Benchmarking Insights

05:44 Challenges in Sales and Buyer Expectations

08:38 The Evolution of Sales Models

11:40 The Role of AI in Sales Dynamics

14:30 Consolidation Trends in Various Industries

17:39 Navigating the New Buyer Landscape

20:31 Reimagining Sales Strategies for Success

23:13 The Evolution of Information Access

25:34 Marketing Strategies in a Changing Landscape

27:23 The Role of Executives in Sales

29:38 Sales Hiring Trends and AI Impact

32:34 Building Strategic Relationships

35:38 The Importance of Post-Sale Relationships

38:34 Navigating the Investment Landscape

41:29 The Future of Sales and Marketing

References in the Show:

https://jurassiccapital.us19.list-manage.com/track/click?u=e3cbd001231a704e4826ed17e&id=28024b7e6d&e=781361f180

https://www.inc.com/brian-contreras/inc-5000-companies-ceo-survey-growing-sales-teams/91222802

Quote of the Show:

"It's hard to hire salespeople because everyone says they're great at relationships. ‘Tell me where you've done that and show me what those results have been,’ should be the follow-up question to that. And then go talk to the parties that are involved within that story or that analogy, and you'll find out really quickly who did what.” - Justin Gray

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 Mark Schopmeyer, Co-Founder and Co-CEO of CaptivateIQ, on how incentive compensation can make or break the success of an early-stage company.

From the critical role of founding AEs to the delicate balance between keeping plans simple and aligning them with big-picture goals, Mark explains why no single model works for every business. They dig into the importance of trust and transparency in compensation plans, how leadership choices shape performance, and why cultural alignment is just as powerful as equity when it comes to motivating teams. You’ll also hear highlights from CaptivateIQ’s latest State of Incentive Compensation report, filled with trends and best practices that modern companies can’t afford to ignore.

Chapters

00:00 Introduction and Team Dynamics

02:51 Incentive Compensation Overview

05:49 Founding AE Concept and Compensation Strategies

08:49 The Importance of Simplicity in Compensation Plans

11:44 Leadership and Organizational Culture in Compensation

14:47 Equity Packages and Early Stage Hiring

17:28 Balancing Risk and Reward in Startups

20:30 The Role of Accountability in Startup Success

27:40 Building a Long-Term Vision

30:42 Incentivizing Performance: Equity vs. Compensation

32:20 Understanding the Bigger Picture in Startups

32:54 Unlocking Outsized Performance through Trust

34:25 The Role of Culture in Compensation

36:07 The Relationship Between Ops and Frontlines

39:02 Building Trust in Compensation Plans

42:21 The Value of High Performers

43:48 Behavioral Insights in Sales Performance

45:20 Integrating Performance Culture Post-M&A

46:28 Incentivizing Beyond Traditional Roles

51:25 The State of Compensation Report

References in the Show:

https://www.captivateiq.com/resources/captivateiq-2025-sales-compensation-benchmarks-report?

https://www.hrdive.com/news/2026-raises-to-hold-steady-compensation/759671/?

Quote of the Show:

"If there's anything I've learned working with startups and early stage companies and early stage founders, there's no correct way to do [things]. There's just a lot of methods to the madness. And I think founding AEs is no different.” - Mark Schopmeyer

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