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.

Top Takeaways

1. Don't fear reassigning key accounts.
Even top performers can adapt; keeping all the best accounts with senior reps creates a revolving door for new hires and stalls team growth.

2. Break the “greenfield trap” for new reps.
Reps in undeveloped territories often fail not from lack of talent, but from poor territory design and lack of enablement.

3. Promotion isn’t leadership readiness.
Great reps often struggle as managers unless they’re taught how to coach, hold people accountable, and operate strategically.

4. Coaching must go beyond deal reviews.
Most managers default to pipeline triage; real coaching means developing skills that affect every deal, not just the current quarter.

5. Internal networks matter as much as external ones.
High-performing reps build relationships across legal, finance, and other internal teams early, compressing ramp time and increasing deal velocity.

6. The best leaders make ideas that help the business, not themselves.
Dan’s biggest promotions came from pitching business-first ideas with no personal gain attached; conviction creates opportunity.

7. Equitable territories create stronger teams.
Giving everyone a real shot at success, rather than over-rewarding tenure, builds momentum and reduces attrition.

8. Friendship and accountability can coexist.
Strong relationships within the team don’t weaken performance; they create the trust needed for tough conversations and high standards.

9. Ask: Are you making the news or reporting it?
Reps who lead the sales process proactively outperform those who simply react to buyer-driven next steps.

10. You can build momentum and hit the number.
It’s not either-or; with the right structure, you can build long-term capability while executing in the short term.