Jeff Keplar, former sales executive at Oracle, MapR, and Google, joins Coach2Scale to challenge one of today’s loudest narratives in SaaS: that product-led growth has made traditional selling obsolete. In this candid, no-nonsense conversation with Matt Benelli, Jeff lays out why complex, high-stakes enterprise deals still demand skilled sellers, strong managers, and real leadership in the field, not just slick UX and freemium funnels. He explains why sales-led growth is often poorly executed, not outdated, and how the caricature of the “golf-playing rep” is holding companies back from serious revenue performance. This episode is a must-listen for CROs, VPs, and FLMs navigating the blurred lines between coaching, leadership, and execution. Jeff unpacks what makes a sales leader worth following, why frontline managers often fail (and how to fix it), and how real coaching, not just pipeline reviews, builds resilient teams. From scaling at Oracle to advising modern startups, Jeff shares lessons that cut through the noise and help leaders build teams that win the right way.
Lessons from Jeff Keplar on What Today’s Sales Leaders Still Don’t Get
I’ve been in enough rooms with CROs to know when they’re telling the truth and when they’re telling the board what they think it wants to hear. Lately, I’ve noticed a pattern. Everyone talks about “transitioning to PLG.” Fewer want to admit what’s actually happening behind the scenes: lagging enterprise pipeline, reps underperforming, FLMs buried in admin work, and managers still unsure how to coach the people they lead.
So I invited Jeff Keplar on the Coach2Scale podcast to talk about it. Jeff’s been in the arena at Oracle, MapR, and Google. He’s built teams. He’s lost sleep over performance gaps. He’s coached through downturns. And now, as an advisor to founders and VCs, he sees the same mistakes play out over and over.
The lesson? Sales-led growth isn’t the problem. Misunderstanding what sales-led really means is.
Titles Don’t Make Leaders. Behavior Does.
Jeff started the conversation with a myth that’s alive and well in most companies: that leadership comes with promotion. A new manager gets a team, a title, and suddenly they’re expected to know how to coach, run a forecast call, and hold reps accountable. But too often, they’ve never been taught how.
Leadership, Jeff said, is earned side-by-side with your people getting the bad news when they do, showing up with them on the tough calls, standing up for them when it counts. If you’re not doing that, no one’s following you. They’re tolerating you.
Sales-Led Growth Has a PR Problem
It’s easy to dunk on traditional sales these days. The blazer-wearing rep, the steak dinner, the golf round it’s become a caricature. But Jeff pointed out something we don’t talk about enough: enterprise sales is still fundamentally human. If your product is complex, expensive, or disrupts workflows, it won’t sell itself.
PLG makes sense for tools that can be adopted in isolation. But if you’re solving a hard problem that cuts across departments, the buying process isn’t linear. There’s friction. Risk. Internal politics. That’s where great reps win. And where frontline managers become make-or-break force multipliers.
Your Managers Are Under-Coached, Underprepared, and Overworked
Jeff didn’t mince words: the FLM role is the hardest job in the company. They’re expected to hit team numbers, coach reps, handle reporting, put out fires, and somehow develop their people all while often being new to leadership themselves.
And here’s the kicker: most were promoted for being great reps, not great coaches. So what happens? They manage deals instead of people. They review pipeline instead of developing skills. And they burn out or fail to deliver consistent performance across their team.
You Don’t Coach Through Forecasts. You Coach Through Trust.
One of my favorite moments from the episode was when Jeff described the difference between coaching and managing. In too many orgs, 1:1s have become either therapy sessions or glorified deal reviews. What gets lost is actual development.
The real job of a sales leader is to help reps sharpen the skills that create the forecast. That means meeting them where they are, knowing what they’re working on, and helping them get better, not just checking the box. If your reps leave a 1:1 unsure of what to work on next, that’s not coaching. That’s oversight.
Great Leaders Advocate When It’s Hard
Here’s where Jeff got personal. He told a story about defending someone on his team who was getting railroaded in a quota dispute. It wasn’t the politically convenient thing to do. In fact, it hurt his standing for a while. But his team saw it. They remembered it.
This is something every CRO should pay attention to: reps know who fights for them. If your FLMs are silent when it matters or worse, if they only manage up you’ll lose trust, engagement, and eventually your top people. Great leaders don’t avoid tough conversations. They have them. And they do it to protect their people.
You Can Be the Boss and Still Be Human
We closed the episode with a conversation that struck a nerve: Can sales leaders be friends with their reps? Jeff says yes with a caveat. Friendship doesn’t mean favoritism. It means trust, care, and knowing your people beyond their numbers.
In a role as isolating and demanding as enterprise sales, those relationships matter. If your reps believe you care about them beyond this quarter, they’ll run through walls for you. That’s how you build a sales team for life, not just for this fiscal year.
Final Word
If you’re a CRO struggling with inconsistent pipeline, low rep productivity, or high attrition, don’t blame the market. Look at your managers. Look at your coaching culture. Look at whether your version of “sales-led growth” is actually being led at all.
And if you’re ready to fix it? Start by listening to leaders like Jeff who’ve done the hard work, made the hard calls, and built teams that win the right way.
Listen to the full episode: “Sales-Led Growth Isn’t Dead, It’s Just Misunderstood.” Available now on YouTube.
