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 GTMnow Podcast
The GTMnow 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.

Visit gtmnow.com for more episodes and other interesting content.