The #1 Question to Ask Yourself Before You Take a CRO/VP Sales Role
Stop overthinking the comp package, the equity split, and the org chart. There’s only one question that matters.
TL;DR: Before you say yes to that VP Sales or CRO role, ask yourself one simple question: “Will I make this a better sales organization than they are now?” If you can’t answer with genuine confidence, walk away. If you can, everything else becomes secondary.
I’ve watched many dozens of sales leaders agonize over CRO and VP Sales opportunities. They’ll spend weeks dissecting the compensation structure, mapping out reporting lines, and calculating their potential upside if the company hits a 3x multiple at exit.
All of that matters, sure. But it’s not what determines success.
The best sales leaders I know—the ones who’ve built legendary teams and driven category-defining growth—all share one trait: they can walk into any sales organization and immediately see how to make it better. Not incrementally better. Significantly better.
You can summarize this all into one question my ex-VP Sales Brendon Cassidy asks: “Can you make this a better sales organization that it is now? Maybe, much better?”
The EchoSign Principle
A former VP of Sales put it perfectly when reflecting on his decision to join Adobe Sign / EchoSign nearly 15 years ago: “The one thing that I always clung to was ‘Will I make this a better sales organization than they are now? Maybe even much better.'”
That was it. Not “Will this make me rich?” Not “Is the CEO someone I want to work for?” Not even “Do I believe in the product?”
Just: “Can I make them a lot better?”
His confidence in that single question led him to join EchoSign. Two and a half years later, Adobe acquired the company for nine figures. The sales organization he built became the foundation for Adobe’s document cloud empire — and went on to be CROs at Rippling, Gong, Brex, Talkdesk, and so many other Cloud leaders.
Why This Question Cuts Through the Noise
When you’re evaluating a senior sales role, you’ll get pulled in a dozen directions:
- The recruiting process will focus on cultural fit and leadership philosophy
- The CEO will pitch you on market opportunity and competitive advantages
- Your network will debate equity percentages and acceleration clauses
- You’ll find yourself lost in spreadsheets modeling different growth scenarios
But here’s what actually happens when you take the job: You walk in on day one, and the sales team looks to you to make things better. The CEO hired you because the current state isn’t working. The board is asking pointed questions about pipeline conversion and sales efficiency.
None of the other stuff matters if you can’t deliver on the core promise: building a better sales machine.
What “Better” Actually Means
This isn’t about tweaking the CRM or running more pipeline reviews. When great sales leaders talk about making an organization “better,” they mean:
Process transformation. Taking a team that’s winging it and giving them a repeatable, scalable methodology that turns prospects into customers predictably.
Talent elevation. Either coaching existing reps to a higher level or bringing in the right people who can execute at the pace and quality the business demands.
System optimization. Building the infrastructure—tools, data flows, compensation plans, forecasting models—that lets good salespeople become great and great salespeople become unstoppable.
Sales velocity amplification. Shortening sales cycles through better qualification, removing friction from the buying process, and increasing average deal sizes by positioning value more effectively.
Learning curve acceleration. Getting new hires to productivity faster and helping existing reps climb the performance curve more quickly through better onboarding, training, and coaching systems.
Cultural shift. Moving from a “hope and hustle” mentality to a professional revenue organization that other departments respect and want to collaborate with.
The Confidence Test
So how do you know if you can deliver this transformation? Ask yourself:
- Have you done this before, or would this be your first attempt at building a sales organization from the ground up?
- When you look at their current process, team, and results, do you see specific, actionable improvements you’d make in your first 90 days?
- Are you excited about the challenge, or are you mostly attracted to the title and compensation?
- Do you have a vision for what this sales team could become, or are you hoping you’ll figure it out once you start?
If you’re hedging on any of these, that’s your answer. Great sales leaders don’t hope they can improve things—they knowthey can, because they’ve seen this movie before and they know how it ends.
Beyond the Binary
The beautiful thing about this framework is that it forces you to think beyond simple success/failure metrics. You’re not asking “Will this company IPO?” or “Will I make enough money to retire?” Those outcomes depend on market conditions, competitive dynamics, and a dozen other variables outside your control.
You’re asking: “Will I do my job exceptionally well?”
If the answer is yes, the rest tends to follow. Great sales organizations attract better talent, close bigger deals, expand faster, and become acquisition targets. CEOs who see their revenue engine transformed become your biggest advocates and references.
If the answer is no, it doesn’t matter what the company does. You’ll struggle, the team will underperform, and you’ll find yourself updating your LinkedIn profile within 18 months.
The EchoSign Lesson
Brendon didn’t join EchoSign because he had inside information about Adobe’s acquisition strategy. He joined because he was confident he could build something better than what existed.
He saw a company with good technology and category white space, but he also saw a sales organization that wasn’t operating at its potential. The gap between current state and possible state was huge—and he knew exactly how to close it.
That confidence turned into execution. The execution turned into results. The results turned into an acquisition that changed the trajectory of everyone involved.
Your Next Move
The next time a recruiter calls about a VP Sales or CRO role, skip the usual dance around comp and equity. Instead, ask for a deep dive into their current sales operation:
- What’s their average deal size and sales cycle?
- How are they generating and qualifying leads?
- What does their sales process look like?
- How do they forecast and manage pipeline?
- What tools and systems are they using?
- What’s the experience level of the current team?
Then ask yourself the only question that matters: “Can I make this significantly better?”
If you can answer with genuine confidence—not hope, not optimism, but earned confidence based on your experience and track record—then you’ve found your next role.
Everything else is just details.
