What happens when a top-performing rep becomes a people-first leader in one of the most demanding roles in tech? In this episode of Coach2Scale, Jeff Perry, CRO at Carta, shares his leadership journey from his early days at Oracle to building high-performing, diverse teams at Carta. He unpacks the misconceptions that still hold sales leaders back, like the idea that only hard-charging, deal-focused managers succeed, or that considerable company experience doesn't translate to startup growth. Jeff challenges these myths with candor, offering lessons for anyone navigating their evolution as a leader.
The conversation tackles why being a “nice leader” isn’t a liability, how to hire from non-obvious backgrounds, and why no one should ever lose a deal alone. Matt and Jeff also dig into the most challenging job in sales, the frontline manager, and why equipping them with the right mindset and tools is the only way to scale performance sustainably. Whether you're a rep, manager, or CRO, this episode will help you rethink how leadership, culture, and coaching intersect to drive lasting results.
Key Takeaways
1. Lean into who you are as a leader
Stop trying to fit someone else’s mold, own your style, values, and story to build authentic credibility.
2. Prominent company leaders can thrive in startups.
Success in enterprise sales doesn’t disqualify you from excelling in high-growth, early-stage environments if you can translate your experience.
3. Empathy and accountability are not mutually exclusive
Being a “nice” leader doesn’t mean being soft; it means building trust so you can challenge and develop your people effectively.
4. Hiring for diversity improves team performance.
Creating teams with varied backgrounds and experiences, not just résumés, leads to more resilience, learning, and results.
5. Balanced team performance is more sustainable than star-centric models
Hitting 115% with everyone contributing beats 130% with a few carrying the load, especially when building culture and scale.
7. Managers should never lose a deal alone.
The best AEs use the entire team, from executives to product, to win; lone-wolf selling is inefficient and risky.
8. Coaching should focus beyond the deal.
Too many 1:1s revolve around the pipeline; great leaders use coaching to build reps’ long-term skills and confidence.
9. Sales leadership is about consistency through volatility
In unpredictable markets, reps need leaders who are steady, transparent, and focused on what can be controlled.
10. High growth creates opportunity, but only for those who embrace it
Carta’s rapid evolution has opened new career paths, but leaders must stay close to the people and remain hands-on to unlock them.
11. Frontline managers need structure and support to succeed
The FLM role is the most overloaded in the org; without tools, coaching frameworks, and clarity, they default to dealing with triage and burnout.