At last year’s RevOpsAF keynote in San Diego, Manny Medina—ex-CEO of Outreach and current CEO of Paid—kicked things off with a line that got a lot of laughs and knowing nods:
“Early in my career, my boss kept telling me to be more strategic. I had no idea what that meant.”
Same, Manny. Same.
For those of us who lean logical and data-driven, that phrase can feel incredibly vague. I spent years trying to decode it. So here’s my best take—hopefully saving you some of the confusion and heartache I had to slog through.
Most of us in RevOps start out taking orders—and that makes sense. Nobody walks into a company knowing what to do. But by the time we’ve figured things out, we’ve lost the fresh perspective of a new hire and the language to describe what’s broken.
Because our entry point is so often grounded in execution—systems, metrics, workflows—it’s hard to make the leap to “strategy.”
Being strategic doesn’t mean you’re suddenly designing GTM strategy or building capacity models from scratch.
It means:
And the most strategic operators? They don’t just execute on a roadmap. They shape it.
Here’s the good news: the goal of every for-profit business is the same—make money, spend less.
Your job in RevOps is to find the friction points that slow that down, calculate the cost of doing nothing, and recommend the right fixes at the right time.
When you frame your work around business outcomes—not tools, not vanity metrics—you get noticed. And you get trusted.
AI can summarize Gong calls and normalize CSVs, but it can’t read a room, sense team dynamics, or figure out what’s actually blocking pipeline. Strategic thinking is about context. You still have job security.
Great operators have range. You need the systems chops and the ability to:
That’s the difference between an IC forever… and a future COO.
Some things feel obviously broken. But not everyone sees what you see—especially if they’re removed from the data or too close to the fire.
Early in my career, I’d throw a chart on the screen, point wildly, and exclaim, “We’re going to miss the quarter!”
Crickets.
No one made changes. Then came the end-of-quarter panic.
Later, I’d walk in with:
That’s when things started to move.
Humans are… human. They have blind spots, biases, and hangups that no amount of dashboarding will fix.
The trick? Don’t take it personally. Learn when to push—and when to stop banging your head against the wall. You won’t win every battle, and that’s okay.
If someone trusts you, they’re more likely to listen when you bring tough feedback.
That doesn’t mean sugarcoating. It means:
That marketing leader with the garbage lead conversion rate? Don’t let sales ambush them in a board meeting. Tell them first. Help them fix it. If they don’t listen? That’s on them.
But you’ll still be someone they want to work with next time.
Let’s say your CFO storms into a meeting and says, “The data is garbage. Fix it.”
Most of us have been there.
You could scramble and start cleaning random fields. Or…
If it’s impacting deals or customer logins? You’ve got a revenue case, too.
Bring your findings back to the CFO with clear trade-offs:
“This will cost $X/month in wasted time. Fixing it pushes back Y project. Worth it?”
That’s strategy in action.
If you can make a data cleanup project strategic, you can make anything strategic.
It’s not about grand visions or perfect roadmaps. It’s about showing how your work fits into the company’s goals—and communicating that in a way others understand.
If leadership doesn’t know why something matters, they won’t know how strategic you really are.
So show them. And then keep going. You've got this.
