GTM 141: Timeless Growth Tips From a $7.4B Oracle Exit and Scaling Carta to $450M in Revenue | Jeff Perry

13 snips

Apr 8, 2025

Jeff Perry, Chief Revenue Officer at Carta and former VP at Oracle, shares invaluable insights on sales leadership and growth. He discusses the importance of mentorship in career development and how to effectively transition from corporate landscapes to startups. Jeff emphasizes balancing empathy with accountability in leadership and challenges the myth that automation replaces personal connection in sales. Additionally, he reveals strategies for scaling revenue and building solutions engineering teams, offering lessons learned from both big tech and the startup world.

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ANECDOTE

Integrating Sun Microsystems into Oracle

Jeff Perry helped integrate Sun Microsystems' sales team after Oracle acquired them.
He applied lessons from this experience, like the importance of solutions engineers, to Carta.

ADVICE

Finding Mentors

Find mentors who are top performers or on a desired career path.
Approach them informally, as formal mentorship programs may not exist.

ANECDOTE

Restructuring Carta's Sales Team

Jeff restructured Carta's sales team to better align experience with deal size.
His most senior salesperson was working on small deals while a junior rep handled the largest enterprise deal.

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Jeff Perry is a truly iconic revenue leader and the Chief Revenue Officer (CRO) at Carta, responsible for core software revenue across New Business, Upsell, Cross Sell, and Customer Success. Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade.

Discussed in this Episode:

How to turn coworkers into mentors—and why it matters.
Moving from enterprise sales leadership to a startup environment.
Why and when to build a solutions engineering team.
The myth of the “18-month CRO lifespan.”
Balancing empathy and accountability as a sales leader.
Why automation isn’t always the best path forward.

Highlights:

06:29 — Mentorship matters. Jeff breaks down how to find and approach mentors—even without a formal program.

12:42 — Lessons from selling servers that still apply to modern SaaS sales

15:02 — Leading through M&A: Inside the culture clash and how Jeff rebuilt a team post-acquisition.

19:07 — Carta’s GTM evolution: How Jeff scaled from one rep selling one product to multiple teams across three business lines.

28:34 — Scaling revenue from $20M to $450M: Advice for CROs entering growth-stage companies.

33:20 — Why “big company” people can thrive in startups—if they leave their playbooks behind.

36:15 — How to use PIPs to coach—not just cut—and what most orgs get wrong.

43:13 — Why the best sellers are quarterbacks, not lone wolves.

46:43 — Pick up the phone: Human connection wins in an era of AI and automation.

Guest Links (Jeff Perry):

LinkedIn: Jeff Perry
Carta: carta.com

Host Links (Scott Barker):

LinkedIn: Scott Barker
Newsletter: The GTM Newsletter

Where to Find GTMnow (GTMfund’s Media Brand):

Website: gtmnow.com
LinkedIn: GTMnow
Twitter/X: @GTMnow_
YouTube: @gtm_now
Podcast: The GTM Podcast (available on all major platforms)

Sponsor: Pursuit

The best talent isn’t actively job hunting. Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers.

If you're hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member.

The GTM Podcast
The GTM Podcast is a weekly podcast featuring interviews with the top 1% GTM executives, VCs, and founders. Conversations reveal the unshared details behind how they have grown companies, and the go-to-market strategies responsible for shaping that growth.

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