As your startup’s revenue and customer base grows, naturally, your sales team will too. There are a lot of challenges that come with moving from your first sales hire, to your first 3-5 reps, to 10-20+ reps and beyond.
I talked to three former Stripe leaders (and my former colleagues!) about our experience building sales at Stripe from a handful of reps to a global org of hundreds, and their advice for other scaling startup teams.
Meet the experts:
- 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
Watch the full masterclass below (or listen audio-only on our podcast) and keep reading for tactics from the panel on managing your sales team and customers at scale.
🌟 1. Hire for the person, not for the role – especially in the early days
If a candidate doesn’t have the full amount or type of experience you’re looking for, don’t let that dissuade you from considering them.
When Geraud started at Stripe, most of the sales team came from non-sales backgrounds. Ryan didn’t have any technical experience when he joined, but he and his colleagues took classes to up-level their technical knowledge.
“I don’t think you aim to hire full-stack AEs,” Ryan said. “You hire people who are motivated to learn, and they become full-stack AEs.”
To identify good candidates, test how they think through problems and gauge how eager they are to learn. Geraud did a mock pitch with all new Stripe reps. See if they’ve looked beyond the front page of your website to prepare, and if they can identify your value props and other strategic points.
Especially in the early days, you want to hire people who can solve problems, think strategically, and are motivated to learn and grow – and who don’t just want to hit their number, but believe in what you’re building.
📈 2. Identify the types of hires you need to get to the next level
In the early days, the Stripe team focused on hiring 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 scalable sales process, though, they just needed salespeople who could execute quickly. “I think if we had hired more of those ‘hunters’ sooner, we could have scaled faster,” Abby said.
When you can clearly define your ideal customer profile and use cases, understand what post-launch success looks like, and feel confident that you can support a larger number of partners – you’re probably ready to start scaling your sales team.
Identify which other hires will help your team and company get to the next level. 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.”
🥇 3. Motivate your team to go above & beyond
Figure out what motivates your team to go above and beyond, and structure your incentives to enable them to do that.
Just like you’ll hire different types of people and roles at different stages, you’ll need to learn how to motivate and incentivize your team at each stage.
For a long time at Stripe, sales reps were salaried. Eventually, it made sense to incentivize and reward reps by switching to being commission-based and having quotas.
“You need to keep a very close eye on the metrics that are coming out of your sales team,” Geraud said. “If you want to keep your top reps after 2-3 years, you have to make the switch to commission at some point.”
🔁 4. Create repeatable playbooks & resources to manage customers at scale
Build a scalable process that enables your reps to add value for customers and close deals quickly.
Before you do anything else: understand your ICP and stick to it. Don’t waste time chasing clients who aren’t a good fit for your product. 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.”
A repeatable process for managing your deals (pre- and post-sale) as you sign more customers is essential. Build playbooks for your reps to follow, with all the steps they need to check off during the selling process. (Do the same thing for your onboarding and success team!)
To keep your customers engaged, use a shared playbook where you can assign steps for them to complete as well. Be clear about the information you need them to share or the tasks you need them to accomplish before your next call.
Beyond playbooks, Abby recommends archiving resources that might be helpful for reps in the future, and having a place to search for answers to common questions.
💪 Bonus: Advice for moving from IC → sales leadership
Are you a rep or AE wondering if moving into leadership is right for you?
Geraud, Abby, and Ryan all made the move from being AEs at Stripe to being sales leaders at their current companies. Here’s why they knew it was right for them:
Geraud: “For me it was natural, because I always enjoyed shadowing calls and giving feedback to other reps.”
Abby: “I’m here to solve really big problems, and that’s what drives me toward leadership. Being strategic, making processes more efficient, building scalable motions – that’s what gets me up in the morning.”
Ryan: “At the end of my IC career, I stopped enjoying the individual wins, and started enjoying coaching new reps. I felt rewarded when I saw people on my team do well.”
Advice for developing your skills and moving into leadership:
- Actively participate in team meetings
- Shadow new hires and give feedback, or lead new hire training
- Join cross-functional company projects
- Take on more than your existing role requires – start doing the next job!
