On a recent episode of Revenue Mavericks, I asked Mike Ogden, VP of Revenue Operations at Cloudflare, about the experience that shaped him as a professional.

He got quiet for a moment, then told me about his childhood.

"I was raised by a single mom. No dad around, no brothers, no sisters. It was me and Mom. At a very young age, I started throwing newspapers because I sort of had to do it. I had a job when I was 10 years old throwing newspapers. I've had a job ever since."

When I asked what inspired a 10-year-old to get a paper route, his answer surprised me:

"Selfishness, really. I knew that as a teenager, I was going to want a car, and that wasn't going to happen unless I bought it. So I started saving money—$100 a month if I was lucky. And so did my mom. She saved for it too."

But here's what stuck with me most. Mike didn't talk about winning. He talked about something deeper:

"Success for me has almost been embarrassing at times. If I won a track meet in high school and I was on the podium, it was almost embarrassing. The winning wasn't the motivator. The motivator for me was that I just hate to lose."

That mentality—the refusal to fail in an environment where there was no safety net—shaped everything about how Mike operates today. And it explains why he's built one of the most thoughtful approaches to revenue operations I've encountered.

Because when you can't afford to lose, you don't organize teams in ways that create unnecessary failure points.

1. When You Can't Afford to Lose, You Don't Build Silos

Most companies structure themselves around what people do: marketers market, sellers sell, customer success manages accounts. It feels logical. It's clean on an org chart.

But here's what Mike recognized through years of operating in high-stakes environments: when you organize around functions, you create unnecessary failure points.

Marketing celebrates qualified leads while the forecast call reveals you're missing your number. Sales hits activity targets while conversion rates crater. Customer success maintains high satisfaction scores while expansion revenue stalls.

The symptoms are everywhere:

  • Different teams tracking different metrics
  • Handoffs that feel like throwing deals over a wall
  • Meetings organized by function, not mission
  • Nobody actually owns the end-to-end revenue outcome

Mike's lived experience—where failure wasn't an option, where he had to "figure out a way" from age 10—gave him a different lens. He couldn't build systems with that many points of failure.

His solution? Map revenue end-to-end first. Then organize teams around that reality.

2. The Revenue Map: Designing Cross-Functional Ownership

At Cloudflare, Mike is implementing what he calls a "Revenue Map"—a framework that maps every touchpoint in the customer journey to the teams responsible for driving it forward, with clear handoff points and shared accountability for outcomes.

The key principles:

Everyone owns pipeline.

Not just marketing. Not just sales. RevOps owns pipeline. Customer success owns pipeline. When everyone owns the same goal, they start measuring success the same way.

One dashboard, different drill-ins.

Everyone looks at the same top-line metrics—pipeline, conversion rates, revenue. Then each function drills into the activities they control that drive those shared outcomes. Marketing doesn't report on MQLs; they report on how their activities contribute to pipeline velocity.

Organize meetings around missions, not functions.

Instead of separate pipeline reviews for marketing, SDRs, and AEs, have one pipeline review where everyone who touches that motion is in the room solving the same problem together. The question shifts from "how's your function doing?" to "how are we collectively moving this forward?"

As Mike put it: "If the outcome is to deliver revenue, we need all the people associated with that process in the room together. We don't need a meeting for marketing, a meeting for SDRs, and a meeting for sales. We're all working to post numbers."

3. The Technology Trap: Too Many Tools Reinforcing the Wrong Structure

Mike also diagnosed why most tech stacks fail to enable cross-functional collaboration: they were bought to solve functional problems, not business problems.

When teams mature independently, they buy tools independently. Marketing gets its stack. Sales gets its stack. CS gets its stack. Before long, you have three tools doing the same thing in different parts of the org—and none of them talking to each other.

His philosophy? "Tools are meant to reinforce the process. That's all they really are. Let's talk about how the business should work, then tools sit on top of it."

The litmus test: Can your dashboards span functions? If marketing, sales, and CS are looking at fundamentally different dashboards, your tech stack is reinforcing silos, not breaking them down.

Why This Matters for Revenue Leaders

Mike's Revenue Map isn't just an operational framework—it's what happens when someone who couldn't afford to lose designs a revenue system.

The best revenue leaders understand this:

  • Design around outcomes before adding functional complexity
  • Create shared visibility so everyone sees the same reality
  • Align incentives across the full revenue lifecycle
  • Build systems that don't create unnecessary failure points

Mike was transparent about the work: "We're better now than we were a year ago, and next year we'll be better than now."

That's the mentality of someone who started saving $100/month at age 10 for a car. Progress compounds. You figure it out. You don't lose.

The companies that adopt this mindset will scale without the constant organizational firefighting. The ones that don't will keep adding functional layers—more tools, more processes, more headcount—and wondering why nothing holds together under pressure.

If you want to hear how Mike is bringing this to life at one of the world's most complex GTM organizations, his full episode is worth your time.