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:
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:
What is The Cheat Code & Friends?
Serial entrepreneurs and operators Justin Gray, Josh Wagner & Sean Kester combine decades of B2B and GTM expertise with unwavering honesty to unpack the latest news (fake or otherwise) on The Cheat Code & Friends Podcast. Combined with a rotating guest list of founders, practitioners and investors, the no-nonsense forum gathers fortnightly, holding court to translate headlines into reality and discuss the impact for early-stage businesses. The Cheat Code is just that, the trusted folks we look to for advice and insight, and we hope to bring the same to you.
Game over.