This article comes from Chuck Marcouiller’s insightful talk at our Las Vegas 2024 Sales Enablement Summit. Check out his full presentation and our wealth of OnDemand resources. 

Let me start with a confession: I’ve built my career by tumbling backward. Most people start small and work their way up to bigger companies. I did the opposite. I spent 20 years at ADP, working in sales and sales leadership. Then, I discovered this thing called sales enablement, and my career took a turn.

Working at a massive organization like ADP has its perks. You get to dive deep into processes and learn how things work at scale. But at the 20-year mark, one of my mentors gave me a nudge: “Chuck, you’ve already proven yourself here. If you’re ever going to try your hand at a pre-IPO company, now’s the time.”

So I made the leap. I joined Avalara, a startup aiming to bring sexy back to sales tax (yes, sexy sales tax—it’s possible!). We grew from 40 to 500 salespeople, went public, and kept scaling. 

From there, I moved to other startups, taking on the challenge of being the first enablement leader through the door. Let me tell you, that first-person-in role? It’s no joke. Another enablement leader once called it a “woodchipper” job, and she wasn’t wrong.

Today, I work as a fractional enablement leader, helping startups navigate the transition to scale-up. If you’re considering taking the plunge into a startup, buckle up—it’s a rocky ride but it’s also incredibly rewarding if you know how to tackle the challenges head-on. 

Here’s what I’ve learned along the way.

The startup reality check

Let me paint you a picture of what typically happens when you join a startup. The founders will tell you, "Hey, join the rocket ship! We're taking off! This is phenomenal! We've got the next big thing!" They'll probably even compare themselves to Elon Musk. 

But when you get there, reality hits – often in the form of unrealistic growth targets (anyone else been handed that casual 97% year-over-year growth expectation?) and minimal infrastructure.

So, why do it? Because the chaos is also an opportunity. You get to build something from scratch, define how things should work, and make an impact that would be impossible in a more structured, established organization. If you’re the kind of person who thrives in that environment, it can be a career-defining experience.

This is where the Revenue Triangle Framework comes in – an approach I've developed through years of hands-on experience in building revenue engines from scratch.

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