23 tactical company building lessons, leanred from scaling Stripe & Notion
#1: Challenge yourself to get more “technical.”
If you’re the first business hire at a startup, you can’t be afraid to get into the technical weeds. How can you shield the product and engineering teams from the more painful elements of deal work, or reduce their customer meeting load?
#3: Ask these questions before joining a startup.
- Are the founders well-suited to build a product in this market? Are they the customer, or do they know the customer well?
- Do they have passion that can be sustainable for decades? “The story of how the Notion founders had to completely start over in 2015 is an example of that grit,” says Cordova. “And when I first met Patrick and John Collison, I had zero context on the problem they were trying to solve at Stripe, but I was fired up by them being fired up.”
- How good are they at telling the company’s story? “Pay attention to how they’re positioning the opportunity when you’re interviewing.”
- Do they care beyond the product? “Many early-stage founders focus just on building a product that people like, which is perfectly fine. But when I was interviewing at Stripe, I saw how they were already thinking about all of the elements that go into building a generational company, from hiring to retention to culture.”
- Are they glossing over the challenges? “In interviews, I like to ask, ‘What area of the business would you say this company is behind on, given its stage?’ This can highlight surprising areas where you may have to fill in cross-functionally.”
- Do I trust the founders to do the right thing if this goes badly? “Will they treat employees right if there are layoffs? Or only a subset of the team gets acquired?”
- Is this someone I think I can learn from? (Even if this person is in a completely different function?)
- Do I feel like the smartest person in the room when I’m with this team? (The answer shouldn’t be yes.)
#7: Go through your own flows — then go through them again.
“At both Stripe and Notion, many of the most successful growth projects involved going through the user experience and putting yourself in the shoes of a first-time customer. It sounds very simple, but you’d be surprised how many organizations don’t regularly do that,” she says. “At Notion, I signed up for a fresh account even though I’d been using the product for years. I went through and clicked every button, writing down every little thing that may annoy users.”
So much of growth is perfecting onboarding. Even if you built your onboarding flow only six months ago, go through it again. You’ll still have bugs.
#9: Don’t fall into the signups trap.
“Stripe’s metric for a fully onboarded customer was receiving three payments from different customers into your account. At Notion, it was inviting at least two other people to your account and putting a certain amount of content in there. Growth is about focusing on engagement, not just getting more people through the door.”
It’s great to have 10,000 sign-ups in one day — but are they paying you? Are they actively using your product? Are they adopting new features? Those are the things that you really need to care about.
#14: Pair first principles with advice seeking.
“We liked Amazon’s ‘working backwards’ approach of writing a press release early on when building new products. Our first riff on that was including ‘User Ships’ in each team’s product plan, effectively forcing ourselves to outline what value we were going to deliver to the user that quarter. It was very similar to what Amazon did, but applied to smaller features and not just big bets.”
#16: As an employee, getting layered sucks. But you can reframe it.
This decision to layer you has little to do with how well you’re performing as an individual. It has everything to do with how well the business is performing. If a startup founder can attract and hire someone with more experience to help grow the business, they will.
If you’re in the midst of a similar situation, here’s her advice: “Turn this into an opportunity to help the company find a new leader and future manager who you believe you can learn from. The only thing worse than getting layered is getting layered with a terrible manager.”
#18: Stand out in recruiting by getting into the financials.
Cordova found that spending time walking candidates through equity made a difference. “Not many companies do this, and very few startup employees have a deep understanding of it. I had a whole spreadsheet that laid out assumptions like, what if Stripe’s value stayed the same, doubled, or quadrupled — how would that affect your equity?” she says.
If you’re a founder facing similar hiring challenges, there are other ways to emphasize that you truly care about the financial outcomes of employees. “Offer the ability to early exercise stock. Extend the option window to exercise to 10 years. And if you sell equity in secondary rounds, offer the same opportunity to tenured employees.”
#19: Try to see “no” as “not right now.”
After joining Stripe, Cordova took this lesson to heart. “I started to take the same approach with potential recruits. Candidates I rejected ended up going on to refer folks who I eventually hired. I remember Rishi Sachdeva turned me down midway through, but eventually came back around and joined my team. I always take a no as ‘not now’ thanks to Greg.”
#22: Make this list before bringing on an opportunistic hire.
When a company starts growing in valuation and getting more press, inbound candidates begin rolling in. “When someone incredibly talented reaches out, you’re tempted to snap them up. But think about who would be complementary to the team you have,” says Cordova.
Take a step back and think outside of this candidate. “Write down the skill-sets you already have on the team, as well as the skills that are lacking. Then go back to the opportunistic candidate and ask yourself — does that person actually fit in my bullet point list? Or am I just trying to fit this square peg into a round hole?”