In this conversation of Coach the Scale, host Matt Benelli sits down with Michael Janes, CRO, investor, and co-founder of Rapid Commercialization Partners, to explore why top sales leaders are shifting their focus upstream. Janes unpacks his core philosophy:
Sell to the strategy behind the capital, revealing how understanding a company’s ownership structure, whether private equity, venture-backed, or founder-led, can dramatically reshape how reps position value, influence internal champions, and align with executive priorities.
From myth-busting the idea that activity volume alone drives results to challenging how most one-on-ones miss the mark, Janes offers a grounded yet forward-looking perspective on what it takes to lead high-performance sales organizations. Listeners will walk away with practical insights on coaching beyond the forecast, the dangers of “super rep” management, and why the real leverage often starts at the board level, not the buying committee. If you’re a CRO or sales leader aiming to uplevel your team and shorten the path to influence, this conversation is required listening.
You can tell a lot about a sales leader by how they talk about capital. Some stay in the weeds features, functionality, pain points. Others look upstream. They know the real buying decisions are shaped long before an RFP is issued and long after the demo is forgotten.
That’s why my conversation with Michael Janes hit a nerve. Michael’s been in CRO roles, investor meetings, boardrooms, and, yes, offshore fishing trips with CEOs. What he shared wasn’t theory. It was a practical roadmap for CROs who want their teams to move beyond the pipeline and start aligning with the real strategy: the capital behind the business.
If you’re responsible for driving revenue across a PE-backed portfolio, a venture-funded rocket ship, or a founder-led company in transition, there are lessons here worth writing on your office wall.
1. “Follow the money” isn’t enough. Sell to the strategy behind the capital.
Michael reframed an old piece of sales wisdom: follow the money. However, he made one crucial addition: understanding the goals of the capital provider.
It’s not just about who signs the check. It’s about why they’re investing, what return they expect, and how your solution fits into the growth or exit narrative. Selling to a founder is different from selling into a PE-backed rollup. If your team doesn’t understand the capital structure, they’re likely selling into the wrong message or, worse, the wrong person.
2. If your managers are only doing deal reviews, you’ve got a coaching gap.
We’ve seen this firsthand at CoachEm. Managers get stuck running forecast meetings disguised as one-on-ones. Forecasts don’t improve skills. They just track outcomes.
Michael called this out directly. He sees real leverage when frontline managers stop playing “super rep” and start actually coaching. That means identifying what skills need to be developed, tracking progress, and spending less time asking “What’s the next step?” and more time asking “What’s the blocker, and what’s your plan to fix it?”
3. Overlay teams only work when they drive access and insight.
As CROs, we’re right to be skeptical of overlays. They eat budget and create confusion unless they bring leverage. Michael built and scaled private equity overlay teams that did just that.
Equip these teams to work directly with investors, identify capital objectives, and initiate top-down sales conversations that unlock stalled opportunities. This isn’t a free-floating layer. It’s a strategic channel to influence decision-making before the RFP ever hits a rep’s inbox.
4. Confidence matters more than permission.
Michael shared one of the more subtle, high-trust moves I’ve heard: telling an executive stakeholder,
“I want you to know, I’ll be sharing insights with your board. Not asking permission. Just making sure you’re in the loop.”
CROs need to embed that mindset into their teams. The highest-performing sellers don’t wait for access; they establish value so early and clearly that they’re invited to the next conversation, not blocked from it.
5. Managers are drowning. That’s your biggest coaching problem.
Most CROs I talk to know this: their managers are overwhelmed, but they’re not sure what to do about it. Managers are undertrained, time-starved, and overloaded with deals, data, and systems. Coaching becomes optional, and rep development gets deferred.
The answer isn’t more enablement decks. It’s creating systems that reduce friction, focus the manager’s attention, and give them simple, actionable insights for every one-on-one. That’s exactly what we’re building at CoachEm because it’s not just a tooling problem. It’s an execution problem.
Final Thought
The most overlooked coaching lever in your organization might not be training, content, or even enablement. It might be whether your reps know who owns the company and what they want.
Give the episode a listen. Michael offers a playbook for how CROs can lead with strategy, coach with precision, and close the gap between capital intent and sales execution.
Let me know what hits home. Better yet, share it with a manager or rep who’s ready to think bigger about how they sell.
Let’s talk: www.coachem.io
