Hey there 👋
Any fellow Toronto startup leaders reading this? 🇨🇦
I’m hosting an invite-only happy hour in the city next Thursday for founders, VCs, and revenue leaders at top Canadian startups… Drake may or may not be making a special guest appearance. 🤫
Figured it was time to step off Zoom for a minute and catch up with the community IRL! 🍻
Interested in joining? Reply to this email & I’ll share the details :)
- Ross
PS: The fun doesn’t stop in TO. We’re planning more events like this in NYC, SF, & others soon. Where else should we be heading this spring/summer?! 🌎
In this newsletter:
- Advice from 3 ex-Stripe revenue leaders on building & scaling sales
- What to look for in your first startup sales hires
- Recommended reads from Spekit’s SVP of Sales & Success
🛠 Lessons learned building the Stripe sales team from scratch
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During my 5 years at Stripe, I worked alongside some incredible colleagues on our journey of scaling the sales org from a handful of reps → a global team of hundreds.
Fortunately, we still keep in touch and I had the chance to talk to three of them this week:
- 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
We held a masterclass on building and leading sales at startups, where we talked about our experience and lessons learned from our time at Stripe.
Here are a few tips from Ryan, Geraud, & Abby on scaling early stage sales:
🧩 Focus on your best-fit customers
Understand your customer profile and stick to it – don’t waste time chasing clients who aren’t a good fit for your product. Especially in the early days, finding best-fit customers who will give you valuable feedback and referrals is critical.
“Find the deals that have momentum and replicate that,” Abby said. “Sales is like dating: if they’re not into you, back off.”
🏋 Invest in support roles early
At the beginning, Stripe AEs handled the entire sales cycle, including integration and customer support. This worked at first, but eventually, they started to become overloaded with admin tasks and post-launch support.
Geraud recommends that startups invest in dedicated onboarding & support roles early on: “If you can solve that problem for your reps faster, they can go close more deals.”
🌟 Hire the right people at the right time
Stripe was great about investing in their team environment and culture from the start, Ryan said. They hired thoughtful people who were good at solving problems and building strategy, even if they didn’t come from sales backgrounds.
After the team figured out a repeatable sales process, though, they just needed salespeople to execute and scale fast. The team also changed their incentive structure – moving from salary to commission-based.
Whatever stage you’re in, identify the type of hires you need to get to the next level, and figure out how to motivate them to go above and beyond.
If you're interested, you can watch or listen to the full masterclass here.
👯 3 tips for finding the right early sales hires
How do you find the right first sales hires for your startup (especially in this competitive job market?)
Here are a few tips from Becca Lindquist, Head of Sales at dbt Labs:
👩🏫 1. Broaden your pool of candidates – figure out what you need people to know before they join, and what you can teach them after
📈 2. Ask for an enablement hire in your first ~20 hires, so all the rep onboarding & ramping isn’t falling on you – this hire can take what you've learned and create a program
🙌 3. Find people who are low ego – they're willing to experiment, fail, and figure things out, and they also aren’t afraid to hire people with more experience than them
Listen to my 15-min conversation with Becca for more early stage sales advice!
📚 Reading recs
What should be on every sales leader’s reading list?
We asked Andrew Bothwell, SVP of Sales & Success at Spekit, and here are his top two recommended books:
The Growth Mindset by Joshua Moore & Helen Glasgow: This book bridges the gap between personal & professional growth, with concrete actions to ensure you succeed in your growth & development goals.
Radical Candor by Kim Scott: A guide for how to be a successful manager while retaining humanity, finding meaning in your job, and creating an environment where people love their work and their team.
What are you reading? Let me know – always looking for something new 💡
Thanks for reading From Vendorship → Partnership! 👋 As always, let me know your feedback on this edition and what you want to see next time.
Ross Rich (CEO and Co-founder)
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