SaaS Sales: The Playbook Every Founder Needs to Scale

When a sales team isn’t hitting its numbers, the instinct is almost always the same: more calls, more emails, more activity.

Tom Stearns and Peter Cleary have spent decades watching that instinct backfire. The real issue, they argue, is rarely effort. It’s the absence of a repeatable, data-driven playbook that translates what a founder knows into something a growing team can actually execute.

In this episode of SaaS That App – Building Tech-Enabled Businesses, Tom and Peter join hosts Aaron Marchbanks and Justin Edwards to break down the most common go-to-market mistakes they see across startups and enterprises alike, and what to do instead.

 

The Founder Knows Everything and That’s the Problem

When a company is young, the founder is the sales team. They built the product because they lived the problem. They know the customer deeply. And that works beautifully…until it doesn’t.

The trouble starts when the company scales. New reps come on board, but the founder’s intuitive knowledge of the customer never gets properly extracted and documented. As Tom put it, “What was intrinsic to what the founder knew. They’re missing the science of deconstructing that.” Instead of building a repeatable system, companies just tell new hires to “go sell” and wonder why results crater.

This is where the playbook comes in. It’s a living framework that captures the four or five data-driven attributes that make a company an ideal customer, and then uses those attributes to focus the entire sales motion.

 

Stop Demoing Every Feature

If you’ve ever watched a founder run a demo, you know the scene: 45 minutes of clicking through every button, every integration, every clever thing the product can do. The prospect’s eyes glaze over somewhere around minute twelve.

Tom sees this constantly. He described walking into companies where reps were trained to showcase every single feature in an hour-long meeting, leaving almost no time for the customer to talk. His fix? Find three problems, demonstrate three solutions. That’s it.

Peter drove the point home with a story from his days at Level 3 Communications. A CTO came into a meeting with Fidelity and spent the entire time waxing poetic about building fiber networks.

The Fidelity team sat there confused, wondering what any of it had to do with their actual needs. “He just wanted to talk about what he loved about what he did with the company, and it had no relevance for what this customer wants.”

 

AI Will Amplify Whatever You Already Have

“AI will accelerate your bad habits.”

Shocking? Probably yes. Yet the reason behind it is quite simple. If your ideal customer profile is vague, AI will help you target the wrong companies faster. If your outbound messaging is generic, AI will blast it to more inboxes at higher volume, torching your domain reputation in the process. Powerful tools, powerful mistakes.

But flip the script, and AI becomes genuinely transformative. Tom described pointing AI tools at CRM data to surface patterns no human would catch: deals stall when the CFO isn’t looped in by a certain stage, or they accelerate when an end user joins an early demo.

Peter added a practical angle that anyone can act on today. Before AI, getting a custom report meant filing a ticket with IT and waiting two months. Now, he tells his teams to define the outcome they want and build a quick script or prompt to pull exactly the data they need.

 

The Playbook Is the Foundation

Sales is a science, not a gift you’re born with. As Peter put it, “Sales is one of the easiest, hardest jobs you can do. What you need to do is pretty simple. It’s just doing it that’s hard.”

The playbook is what makes the doing possible at scale. Without it, you’re just adding headcount to a broken system and wondering why the graph won’t go up and to the right.

So before you post that next sales rep job listing, ask yourself: do I actually have a playbook? Or am I just hoping the next hire figures it out the way the founder did?

 

Tom and Peter’s Backgrounds

Tom Stearns is the founder of Stearns Consulting, specializing in helping SaaS companies deconstruct and rebuild their go-to-market strategies from the ground up. With a background in fine arts and three decades of experience spanning graphic design, marketing, and sales, Stearns brings a unique perspective to sales process optimization.

Peter Cleary is the Senior Manager at Akamai Technologies, bringing decades of enterprise sales and sales engineering expertise to complex B2B environments. With a background in history and extensive experience managing large-scale sales teams, Peter advocates for treating sales as a teachable science rather than an art form.

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