E46: The RevOps Mind Behind Owner.com’s Billion-Dollar Valuation: Steve Dinner
The RevOps Leader Who Thinks Like a Rep: How Steve Dinner Built Owner's Revenue Infrastructure Differently
Programming note: I’m sure you’ve all noticed that my rate of writing has gone down over the last few months and we’ve missed some weeks with new episodes. To be honest, this summer wasn’t an easy one for me with my dad suddenly passing, a move from Toronto to the Bay area and a few other family emergencies thrown in for good measure. I’m back on my feet now and excited to have more time for the pod and writing. I have some big ideas in my notepad that I’m excited to share and I’ll be publishing a few presentations (GTM25, Vertical Software Summit, etc) to you guys in the next month. Sorry for the intermittent publishing and I’m excited to get back engaged with this amazing community. I love hearing from you guys and I missed all of the thoughtful responses and opinions so keep those coming!
Now onto last week’s episode (8 days late 😬)!
This week's episode is a special one because I interviewed my VP of RevOps, Steve Dinner, who I've worked with hip to hip for almost nine years now. A bunch of people have asked me to do this episode over the last year, but I avoided it because it seemed like shameless Owner self-promotion. Shoutout to Jessica Ashar for the persuasive nudge!
Many revenue leaders think their RevOps function exists to manage technology and enforce process compliance. They hire for technical expertise, optimize for system efficiency, and wonder why their sales teams treat RevOps like the enemy.
This conventional approach misses a crucial psychological element: the moment you start treating reps like metrics on a dashboard rather than humans trying to do their jobs, you've already lost. Your team will live down to those expectations. The validation fields multiply, the friction increases, and suddenly your RevOps team becomes what Steve Dinner calls "the no team" and is completely disconnected from the reality of the rep experience.
Steve Dinner, VP of RevOps at Owner.com, has taken a radically different approach. Starting as a BDR manager who happened to think in systems, he's built a RevOps function that operates from a core belief: people inherently want to do well. Give them the right workflows, reduce cognitive load, and they'll naturally do the revenue-generating activities you want.
The results speak for themselves. Owner has scaled from $5M to $50M+ ARR since Steve’s arrival with a RevOps team that's seen as a strategic partner rather than a roadblock. In our conversation, Steve unpacked the philosophy and frameworks that make this possible.
We explored why his monthly ride-alongs sitting beside reps making cold calls are more valuable than any dashboard, how an Agile transformation turned his team from reactive firefighters into strategic operators, and why the best RevOps leaders might not be the most technical ones. Steve also shared the exact framework he uses to avoid becoming either a "yes team" that takes every request or a "no team" that blocks progress and revealed what CROs consistently get wrong when hiring their first RevOps leader. I hope that more revenue and RevOps leaders in building infrastructure that amplifies human capability rather than constraining it.
1. The Empathy Paradox: Why Former Reps Make Better RevOps Leaders
Here's what most companies get wrong: they hire RevOps leaders for technical proficiency and wonder why there's a disconnect with the sales team. Steve's path was inverted - he was a rep who discovered he thought programmatically.
"I can't imagine how hard it would be to do what I do well without knowing really what it means to be staring at the dial button," Steve told me. This isn't just about understanding the sales process intellectually. It's about visceral memory - the anxiety before a cold call, the cognitive load of context switching, the frustration when systems get in your way.
The practical application: When Steve does ride-alongs (which he does monthly), he's not just observing. He's reconnecting with that emotional reality. "Even just sitting down and looking at the call button... registering the feelings and emotions that you have going through your head. It's enough to rekindle the empathy for how challenging the job is."
This empathy translates into design philosophy. Instead of asking "how do we force compliance?" Steve asks "how do we make the right action the easiest action?" It's behavioral economics applied to revenue operations - what Thaler and Sunstein call "nudge theory" in their seminal work.
2. Trust as Architecture: Building Systems for Smart People
Steve shared a story that crystallized his entire philosophy. Early in his career, he created a simple dashboard showing what percentage of calls went to tier-one accounts. No rules, no enforcement, just visibility.
Day one: 40-45% of calls to tier-one accounts. Day two: 70%. Day three: 80%.
"People inherently, especially if you're hiring well for the correct roles... they want to do well," Steve explained. This runs counter to what Douglas McGregor called "Theory X" management - the assumption that employees are inherently lazy and need constant supervision. Steve operates from Theory Y: people are self-motivated and thrive with autonomy.
The framework in practice:
Make the golden path the lowest friction path - Use tools like Momentum to pull information automatically rather than forcing manual entry
Add friction only where absolutely necessary - Reserve validation fields for true deal-breakers
Provide visibility, not surveillance - Show reps their metrics in context of success, not punishment
As Steve puts it: "If you give them the right workflow and it actually solves for the challenge that prevents them from doing the next best action... you're going to get the result you're looking for."
3. The Agile Transformation: From Ad Hoc to Systematic Excellence
About a year ago, Steve's team underwent an Agile transformation that fundamentally changed how they operate. This wasn't about following a textbook - it was about creating what he calls "turning variables into constants."
The framework involves:
Product Owners for each function (Marketing, Sales, Launch, CS)
Two-week sprints with clear definitions of "ready" and "done"
Systematic retrospectives that generate 5-15 improvements each cycle
A working contract that defines exactly how the team interfaces with the business
"Without that, it's super easy for things to fall through the cracks," Steve noted. But more importantly, it gives RevOps the ability to say "here's what we're working on, here's when you can expect it, and here's what needs to wait."
This addresses what researchers at MIT's Center for Collective Intelligence call "collaborative intelligence" - the ability of groups to work together effectively. By creating clear processes and communication channels, Steve's team can handle multiple strategic initiatives simultaneously rather than lurching from fire to fire.
4. The Yes/No Trap: Finding the Middle Path
RevOps teams typically fall into one of two dysfunctional patterns. They either become the "no team" (overwhelmed, defensive, disconnected) or the "yes team" (people-pleasing ticket-takers who never address root causes).
Steve's approach transcends this binary through what he calls "collaborative solution design":
Instead of saying no: "Let me understand what you're trying to achieve and what happens if it doesn't get done."
Instead of saying yes to everything: "Here's how this fits into our broader priorities. If we do this, here's what we're trading off."
This requires what Amy Edmondson calls "psychological safety" - the belief that you won't be punished for disagreement or asking questions. Steve builds this by being radically transparent about trade-offs and inviting stakeholders into the prioritization process.
"Every individual contributor, you have to be able to trust the people around you... they're inherently reasonable," Steve explained. "If you're hiring well, these are people who are focused on the company outcome."
5. The CRO-RevOps Mind Meld: Why Philosophical Alignment Matters More Than Technical Skills
When I asked Steve what CROs should look for in a RevOps leader, his answer surprised me: "You have to define the constraints that your business has. It's going to tell you exactly what kind of leader you need."
For Owner, operating in high-velocity SMB with hundreds of thousands of accounts means RevOps needs to be about workflow optimization and business strategy. The data science complexity lives in a separate function. In an enterprise environment with long sales cycles, the requirements would be completely different.
The hiring framework:
Define your constraints - What kind of business are you? What problems need solving?
Look for philosophical alignment - Can this person think like you think? Can they make decisions in your absence?
Prioritize revenue leadership capability over technical prowess - "There are ways to fill technical gaps. There's not really an easy way to fill a revenue leadership capacity gap."
Test for empathy - Have they been in the trenches? Do they understand the human side of sales?
As Steve puts it: "If you can't see this person as somebody who you're going to give a seat at the table... then you're still looking."
The Owner RevOps Playbook: Bringing It All Together
What makes Steve's approach revolutionary isn't any single innovation - it's the philosophical coherence of the entire system. Every decision flows from the core belief that people want to succeed and systems should enable rather than constrain them.
The practical implications cascade through everything:
Monthly ride-alongs maintain empathy and catch friction early
Agile processes create predictability without rigidity
Philosophical alignment enables distributed decision-making
Trust-based design reduces cognitive load and increases adoption
This isn't just feel-good management theory. It's grounded in decades of research on human motivation, from Herzberg's Two-Factor Theory to Deci and Ryan's Self-Determination Theory. When you treat people as competent agents rather than compliance problems, they rise to meet expectations.
Additional Considerations
Related frameworks to explore:
OODA Loop (Boyd): Steve's rapid iteration cycles mirror this military decision-making framework
Cynefin Framework (Snowden): Helps categorize problems as simple, complicated, complex, or chaotic - useful for RevOps prioritization
Theory of Constraints (Goldratt): Steve's focus on removing bottlenecks aligns with this operations management approach
Further reading:
Working Backwards by Colin Bryar and Bill Carr - Amazon's operational excellence playbook
The Hour Between Dog and Wolf by John Coates - neuroscience of performance under pressure
Thinking in Systems by Donella Meadows - foundational systems thinking