Millions in Runway Burned

Over the last few weeks, I’ve met with a handful of technical founders.  After enough conversations, I’m no longer surprised to meet brilliant engineers who can architect complex systems but struggle with basic GTM execution.  Two patterns keep emerging that are costing these founders millions and months of precious time. 

Mistake #1: The Premature CRO Hire

The Founder: Let’s call him Beau.  He runs a seed-stage FinTech with top-tier VC backers.  He has deep industry experience and is one of the sharpest people I know.  But when we started talking about his “CRO” I had to cut him off mid-sentance.

The Problem: Before closing many deals himself, Beau hired a “seasoned executive” with 20+ years of experience to help land his first enterprise deals…and now he’s feeling the pain.

As Bardia Shahali, VP Sales @ Fireworks, called out in a his recent GTMBA Leadership Spotlight  “companies hiring seasoned execs to run early-stage companies are taking a big risk.”  

Hiring a CRO before you’ve figured out some process yourself is like hiring a head chef before you know how to boil water.  

GTMBA Approach: A few months back, we partnered with guest contributor Dan Oakes who interviewed 41 Founding AEs.  A few takeaways:

• Founders should complete several full sales cycles (ideally 10+) with non-network customers

• Hire a Founding AE first, not a CRO

• Stay involved in early sales cycles for rapid feedback loops

In addition to hiring too early, in my opinion, Beau hired wrong.  I asked Beau, “how does your CRO use AI in deals.”  Beau responded, “he doesn’t.”  

We’re in 2025.  Not testing for AI aptitude in GTM interviews is like hiring an investment banker who doesn’t know Excel.  Your “seasoned executive” risks being seasoned in obsolete methods.

Founder 2: The Champion Who Wasn’t

The Founder: Hugo - runs a customer support AI startup.  Sharp founder, but new to enterprise sales.  He’s been stuck in procurement purgatory for 2 months with no end in sight.  

The Problem: Within 30 seconds of discussing, I diagnosed the problem in this deal - no champion. 

Hugo’s core buyer is Operations, but he’d been working closely with a technical stakeholder who told him on their first call, “I can be your champion for this deal.”  

Red flag.  When a prospect tells you they’re your champion, your spidey sense should be tingling. Self-proclaimed champions are usually just Coaches (helpful), or worse, Faux-Champions (deal killers).  

GTMBA Approach: Champions don’t talk about being champions - they show they are champions through actions.  Four areas to stress test: 

1. Personal Pain: Experiences enough pain to drive change personally

2. Active Advocacy: Actively advocates for your solution over alternatives

3. Organizational Influence: Has influence with economic buyer and cross-functional stakeholders

4. Determination: Demonstrates determination and ability to move deals forward

As Andy Whyte at MEDDICC says, “A Champion without Power and Influence is just a Coach.”  Hugo’s contact proved to be a Coach - he was strong on qualities #1 and #2, but lacking on #3 and #4.   

I suggested that Hugo confront his Coach with a personal story about a deal that went sideways when a “technical stakeholder” tried to drive a deal forward and how it wasted everyone’s time.  His contact’s reaction would determine whether he could unblock through proper introductions or should qualify out.  

Coaches can be extremely valuable if you understand their role.  Yesterday, I met with a self-proclaimed “champion” in a deal who helped build a compelling business case for his business unit, but couldn’t drive the pilot forward.  We had to find a Champion in a different org to get the pilot going, but kept our Coach engaged and activated him for the pilot readout as a Windsurf advocate.  

As an AE, I have the luxury of spending more time investing in Coaches and Champions.  However, as a start-up founder, you need to ruthlessly prioritize time.  If you don’t have a champion, qualify out and spend time on another deal.  While you still might get the deal across the line without a champion, your ROI will take a big hit - deal cycles will drag out and your final contract value will be significantly lower. 

Bottom Line

Technical founders often nail the product but stumble on GTM fundamentals. 

My advice: when hiring, don’t hire seasoned executives to solve problems you haven’t learned to solve yourself. When running a start-up deal cycle, don’t confuse enthusiastic coaches with champions who can actually get deals done.

Disclaimer: Names of the founders referenced in this article have been anonymized to protect their identities