What happens when your top-performing rep becomes a struggling front-line manager? In this episode, Dan Freund, Chief Sales Officer at Invoice Cloud and former Oracle sales leader, unpacks the leadership gap plaguing high-growth sales orgs. From rethinking territory design to balancing equity with accountability, Dan shares how he transformed underperforming teams into consistent winners, without clinging to sales superstars or status quo assumptions.
This episode offers a candid look at the hard decisions CROs and sales leaders must make to scale performance without sacrificing culture. You’ll hear why conviction matters more than consensus, how to spot reps ready for more than just promotion, and why internal networks can fast-track productivity. If you’re tired of recycling the same top 10% and ready to build a coaching culture where every position matters, this conversation will shift how you lead.
Lessons from Dan Freund, Chief Sales Officer at Invoice Cloud
There’s a pattern I’ve seen more times than I’d like to admit.
A top-performing rep gets promoted to front-line manager. They’ve crushed quota, built strong customer relationships, and seem like a no-brainer for leadership. But six months later, they’re overwhelmed. The team is underperforming. Attrition is creeping in. What happened?
In this week’s Coach to Scale episode, I sat down with Dan Freund, someone I’ve worked with for over a decade and one of the most thoughtful sales leaders I know. Dan’s held senior sales roles at Oracle, Brightcove, Brandwatch, QuickBase, and now serves as Chief Sales Officer at Invoice Cloud. He’s built high-performing teams, reorganized territory models, and, maybe most importantly, learned when to challenge the conventional wisdom that holds organizations back.
Here’s what stood out in our conversation. If you’re a CRO trying to drive consistent, scalable growth, this isn’t theory. It’s execution at its best.
1. High Performers Don’t Automatically Make Great Leaders
Dan was blunt about it: being great at selling doesn’t mean you’re ready to lead. Leadership means making decisions that serve the business, not just your number. It means coaching people through skill gaps, not just running forecast calls. And it means giving up control and learning how to empower others.
One of his best reps-turned-managers once admitted, “I didn’t know what good looked like.” That’s not incompetence, it’s an organizational failure to teach leadership.
2. Stop Protecting Territories and Start Building Teams
Too many sales leaders cling to the idea that senior reps “own” certain accounts. Dan pushed back on that hard. When he reshuffled territories at Oracle, cutting down named accounts, removing manufacturers, and distributing new books of business,he heard all the usual objections.
But here’s what happened: new hires ramped faster, performance evened out, and for the first time, every rep hit quota. It wasn’t about playing favorites; it was about creating structural fairness and giving everyone a real shot to succeed.
3. Build a Culture Where Ideas Win, Not Egos
One of the most compelling stories Dan shared was about pitching an SMB strategy that wasn’t even in his scope. No power play. No self-interest. Just a conviction that it was right for the business.
That pitch led to one of the biggest promotions of his career. Not because he asked for it, but because he built something that made the business better. That’s the kind of leadership CROs need to nurture. Not consensus-building. Conviction.
4. Don’t Just Coach the Deal. Coach the Rep.
There’s a phrase Dan used years ago that still sticks with me: “Are you making the news, or reporting the news?” Too often, reps and their managers are just reacting. Running through call notes. Talking about next steps, they didn’t control.
True coaching means asking tougher questions. What’s the skill holding this deal back? Why is the customer hesitating? What’s your plan to change that? When you start coaching to skills instead of just sales stages, you lift the floor and the ceiling of performance.
5. Internal Networks Drive Faster Ramp and Better Execution
We talk a lot about external networking, but Dan highlighted something most CROs overlook: the power of internal networks. One of his best hires didn’t just chase pipeline, they grabbed lunch with SEs, invited legal out for drinks, and knew who to call when an exception needed escalation.
Sales is a team sport. The reps who figure that out fastest win faster. And if you’re not teaching your new hires how to navigate internally, you’re adding months to their ramp.
6. Consistency Beats Charisma
One of Dan’s biggest influences wasn’t a CEO, it was his high school football coach. Every position mattered. Every practice had a plan. No one got special treatment. That lesson shaped how he builds teams today.
When expectations are clear and leadership is consistent, reps feel like they have a shot. They know what good looks like. And they know they’ll get coached, not just judged. That’s what keeps people from quitting. That’s what builds culture.
The Bottom Line for CROs
If you’re sitting in the CRO seat, here’s the call to action:
Don’t promote another rep without a leadership development plan.
Don’t design territories that only make sense to the people who’ve been there the longest.
Don’t confuse deal inspection with people development.
Instead, start building a system where coaching isn’t a “nice to have,” but the backbone of performance. Create the conditions where managers can lead, not just survive. And reward the people who think like owners, even when the idea isn’t popular.
Dan Freund’s career is proof that you don’t need to chase titles to get ahead. You need to back what’s best for the business and build teams that can scale with it.
🎧 Listen to the full episode: available now on YouTube, Apple Podcasts, Spotify, and at CoachEm.io.
