The churn rate in GTM roles is notoriously higher than in any other function. The sophomoric justification for this is to blame it on the hire by saying that “marketing and sales people are great at selling themselves,” and thus “unqualified” candidates get through the process at a higher rate. The reality, and I’ve been through this personally with GTM hires, is that the body often rejects the organ not because the organ is bad, but because the body is sick. 

Senior GTM leaders often join companies under immense pressure to “fix growth” and, in some cases, “save the day.” Many great hires fail not from lack of skill or drive, but from misaligned expectations, unrealistic goals, weak foundations, or lack of alignment and prioritization. Before accepting your next role, take time to truly understand the business, its team, and its backers with the same rigor an investor would. Knowing the right questions to ask during that process can help you navigate the tricky process of getting an offer and ensure it’s one you actually want.

1. Clarify the Growth Thesis and Investor Expectations

Every investor has a narrative. Know it.

• Questions to ask:
  
  
  
  • What’s the investor’s thesis for this company and horizon for exit or liquidity? In the case of multiple investors, are they all aligned?
    
  • What milestones are tied to the next round or valuation step-up?
    
  • How has board pressure changed over the last 12 months?
    
  • Warning signs: The board expects exponential top-line growth without new capital or insists on conflicting goals. For example, “triple growth and improve margins by 20%.” One investor might prioritize profitability at Series A, while another at Series C focuses on top-line growth.

2. Understand the Real Financial Picture

Ask to see the funding history, burn rate, and runway.

• Questions to ask:
  
  
  • What is the company’s current cash position and monthly burn?
    
  • What assumptions underpin the next raise?
    
  • How much control do existing investors have over spending and hiring?
    
  • Warning signs: Leadership dodges questions about cash, delays fundraising discussions, or quotes vanity metrics instead of revenue or contribution margin.
    

3. Map the Org and Power Dynamics

Titles can mask dysfunction. Understand who truly owns decisions and budgets.

• Questions to ask:
  
  
  • Who owns pricing, product roadmap, and customer success?
    
  • How are sales, marketing, and product held accountable, jointly or separately?
    
  • What are the informal power centers?
    
  • Warning signs: C-suite turf wars, unclear authority lines, or a founder still micromanaging GTM after claiming to “hand it off.”
    

4. Ask for Historical and Forward Metrics

Successful companies show their math.

• Metrics to review:
  
  
  • CAC/LTV trends over 12–24 months
    
  • Pipeline source mix and conversion rates
    
  • Net revenue retention (NRR) and churn per cohort
    
  • Gross margin and contribution margin by segment
    
  • Warning signs: Missing cohort data, “trust us” answers, or inconsistent definitions of metrics, such as CAC excluding salaries.
    

5. Run Back-Channel references.

Quiet diligence reveals more than glossy decks.

• Ask current employees: Would you work for this CEO again? What’s the biggest internal challenge the company faces? Are priorities and goals aligned with resources?
• Ask former employees: Why did they leave? What caused friction between GTM and product?
• Ask investors (discreetly): How does this company compare to others in your portfolio at the same stage? What do you see as the single greatest barrier to success?
• Ask customers: What’s the biggest reason you would or wouldn’t recommend them?
• Warning signs: High leadership turnover, poor product-market fit masked by promotions or incentives, or investors unwilling to discuss metrics candidly.
  
  

A senior hire’s failure often traces back to information asymmetry. Great GTM leaders treat the interview process like due diligence, looking not just for opportunity but for risk. Ask the hard questions early. It’s far better to walk away from a role that’s not set up for success than to spend eighteen months trying to fix a business model that was never viable.