The 5 Biggest Pitfalls in Vertical SaaS GTM
(and How to Avoid Them) — Ryan Heaphy
About the Speaker
Ryan Heaphy has built and scaled 100+ vertical SaaS go-to-market teams. Over the years, Ryan has led growth strategies — from early-stage SDR models to enterprise expansion — helping companies navigate the common pitfalls that trip up founders. In this episode, he shares actionable lessons from real-world experience: how to hire, when to scale, and how not to fall into the most dangerous GTM traps.
Sneak Peak
Summary
In this kickoff episode of The Vertical SaaS GTM Playbook, Riley Soward sits down with Ryan Heaphy to uncover the Top 5 go-to-market mistakes founders make when scaling vertical SaaS. They dive into why many early hires fail, how “free pilots” sabotage momentum, the nuances of SDR deployment, and how to approach enterprise deals without blowing your growth plan. Whether you're pre-product-market fit or scaling toward $10M+, this conversation is packed with lessons you can act on now.
Key Takeaways
Hire only when your playbook exists - Without a documented and repeatable sales process, new hires flounder. Ryan underscores that hiring early without structure is a top mistake.
Beware “free pilots” - While tempting, free pilots often attract uncommitted customers. They waste time and create false expectations.
SDR models aren’t universally good - The SDR approach can be powerful — but only when it fits the stage and business model. Misapplication drives dysfunction.
Don’t over-index on industry experience - Ryan challenges the notion that only industry veterans can sell in vertical SaaS. Grit, coachability, and sales instincts matter more.
Enterprise sales needs guardrails - Chasing big deals without a plan or clarity invites scope creep. He discusses how to de-risk enterprise moves and how a single well-executed deal can change your business trajectory.
Clarity and expectations are non-negotiable - Communication and alignment with enterprise buyers on scope, security, and commitment is critical to avoiding deal failure.
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