Matt Benelli sat down with Mark Roberge last year, former CRO at HubSpot, Harvard Business School professor, and co-founder of Stage 2 Capital, to challenge some of the most persistent myths in sales leadership. From debunking the idea that top reps make the best managers to exposing why shadowing high performers can actually backfire, this conversation delivers a candid look at why most coaching programs fail to scale and what to do instead.
Mark lays out a structured, repeatable approach to frontline coaching that not only boosts individual rep performance but transforms how entire sales organizations operate. He shares why focusing on team attainment is less useful than tracking the percentage of reps hitting quota, how managers can move from reactive fire drills to proactive coaching cycles, and why self-diagnosis is the new sales superpower. If you’re a sales leader still stuck on the hamster wheel, this episode offers a way off.
Most sales organizations are stuck in the same pattern: a few top performers carry the number, frontline managers run from fire to fire, and reps sit through 1:1s that feel more like pipeline triage than performance development. We call it the hamster wheel. Everyone’s moving fast, but not many are actually getting better.
That’s exactly what we unpacked with Mark Roberge, former HubSpot CRO, HBS professor, and co-founder at Stage 2 Capital, in this episode of Coach2Scale. Mark’s built and studied hundreds of sales teams and came to one simple conclusion: coaching is the lever, but almost no one is pulling it right.
Here’s what stood out.
1. Star Reps Make Lousy Managers
Mark didn’t mince words. Promoting your top rep to a management role is usually a mistake. The characteristics that make someone a strong individual contributor, competitiveness, independence, instinct,rarely translate into effective coaching behaviors. Leadership requires a different skill set: patience, the ability to tailor feedback, and an eye for diagnosing skills gaps. Most star reps haven’t developed those muscles.
If you’ve promoted someone because they “crushed quota,” take a second look at how they’re developing their team. If they aren’t, you might be eroding performance from the inside.
2. Stop Telling Reps to Shadow Top Performers
Letting new reps shadow your best AE feels intuitive, but it’s lazy enablement. Top performers often bend the process to their strengths and those strengths are rarely replicable. That’s how bad habits spread. Instead, onboarding should be built around a clearly defined sales process, so reps can internalize the fundamentals before adapting them.
Coaching starts by giving everyone the same sheet of music. Mastery happens later. Consistency first, creativity second.
3. Coaching Can Scale, But Only If It’s Operationalized
This was the core of our conversation. Mark shared a simple but powerful approach: each manager meets monthly with their director, and each director meets with their VP, to discuss every rep’s skill diagnosis, the plan to improve, and the metric that proves progress. It cascades from rep to CRO.
This isn’t theoretical. It’s how HubSpot grew from zero to $100M. Coaching becomes part of the operating cadence, not something managers “try to make time for.”
If your managers aren’t doing this today, they’re reacting. And reaction doesn’t scale.
4. You Can’t Improve What You Misdiagnose
Reps often don’t know why they’re struggling. And truthfully, most managers don’t either. They throw generic feedback at performance problems: prospect more, be more confident, drive urgency. But without data to isolate the real issue, stage conversion rates, win-loss by persona, and talk tracks they’re just guessing.
As Mark put it, “Data tells you where to look. But only qualitative review, call listening, and deal inspection can tell you what’s broken.” It’s a two-step process. Skip either one, and you’ll coach the wrong problem.
5. Measure % of Reps Hitting Quota, Not Just Team Attainment
This one hit hard. Mark’s Series A investor at HubSpot only ever asked him one question: What percentage of reps hit quota?
Why? Because if only 30% of your team is making quota but the number gets hit, it means you’re over-relying on a few heavy hitters. That model doesn’t scale, and it sure doesn’t retain talent. High rep success percentage correlates with culture, predictability, and long-term revenue expansion.
CROs: Add that metric to your board slides. Immediately.
6. Great Coaching Teaches Reps to Self-Diagnose
In Mark’s words: “If I start putting poorly mid-round, I know how to fix it because I was taught the fundamentals.” That’s what you want for your reps. Not dependency on their manager. Not guesswork. But the ability to recognize what’s breaking and adjust in real time.
That only happens when you consistently coach the skills behind the results. The forecast doesn’t improve because you yell louder. It improves because the skills that drive its discovery, qualification, and urgency creation get better week by week.
The Bottom Line
If you’re a CRO tired of fighting for marginal gains, you don’t need more tech. You don’t need another SPIFF. You need a coaching system that gives managers the time, structure, and insight to develop reps at scale.
That’s what we built CoachEm to do. Mark’s blueprint is proof it works. If you want to escape the hamster wheel, this episode is your first step off.
🎧 Listen to the full episode: on [Spotify / Apple / YouTube]
