Building & Leading Startup Sales, Featuring Former Stripe Leaders

Welcome back to the From Vendorship → Partnership podcast, Season 2: Seller’s Journey! 

This season, we’re talking to B2B sales leaders about their experience building winning processes, coaching & scaling teams, and partnering with customers.

We have a special episode this week: we’re sharing a masterclass we held with former Stripe sales leaders (and Ross’ former colleagues!) who are now leading sales at other companies:

• Ryan O’Holleran, Director of Enterprise Sales at Airwallex
• Geraud Gonzales, Director of US Partner Sales at PayPal
• Abby Westby, Head of Platforms at Parafin

They talked to Ross about their experience building and scaling the Stripe sales team together, tips for moving into leadership roles, and other advice for startup sales teams.

Listen to the episode, or you can watch the full session & get key takeaways below!

💭 What’s a key lesson you learned while helping build the sales team at Stripe?

When Geraud started at Stripe, the sales team was six people, and only two of them (Geraud included) came from sales backgrounds.

He shared three key lessons learned while building the Stripe sales team:

1. Understand your customer profile and stick to it: Don’t chase clients who aren’t a good fit – they won’t end up being a good customer who can give you critical feedback and referrals.
2. Become a master of the technology, especially at a startup: Always be looking to learn and deeply understand your product.
3. Work with other reps: split deals and be collaborative, instead of trying to sell everything by yourself.

🔮 If you could go back to the beginning of your journey scaling the Stripe team, what would you do differently?

In the early stages at Stripe, Abby said, the team intentionally hired a lot of thoughtful people with non-sales backgrounds – people who were good at solving problems and figuring out the process and strategy.

“That worked really well at the beginning, but one thing we could’ve done better was hiring enough salespeople fast enough once we had a scalable process,” Abby said. “At that point, you just need to fill the gap so you can scale faster.”

💼 What advice do you have for reps and AEs wanting to move from being an IC to being a sales leader?

“At the end of my IC career, I stopped enjoying the individual wins and started enjoying coaching and training new reps,” Ryan said. “I felt rewarded when I saw my team do well.” If you start to feel the same way, it’s a sign that leadership might be the right path for you. 

To develop your leadership skills and put yourself on that path, start taking on responsibilities and learning things outside of your IC role. This could involve leading new hire training, mentoring your team, working cross-functionally with other departments, etc.

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About the guests:

Ryan O’Holleran, Director of Enterprise Sales at Airwallex – formerly part of the founding sales team at Stripe, helping the company scale from 200 to 5,000+ employees

Geraud Gonzales, Director of US Partner Sales at PayPal – global payments sales executive with 9+ years of experience; previously helped build the Stripe sales team

‍Abby Westby, Head of Platforms at Parafin – experienced sales leader focused on startup sales; formerly an early member of the Stripe sales team