Building, growing, and scaling startup teams: a conversation with Stripe, Nourish, and Ramp

Product, hiring, and processes—these are three critical components that startups need to nail to be successful.

Ramp’s VP of Product Geoff Charles recently sat down with Stripe’s Sophie Sakellariadis (Head of Product) and Nourish’s Stephanie Liu (CTO) to discuss the different approaches they’ve taken to hiring, company culture, and team structure to drive velocity.

Find talent that matches your company’s DNA

The earliest hires are building the company's foundation. In addition to assessing skills, startups must be incredibly clear about culture fit.

Nourish does this by publishing company values on its website. But they are not your typical generic statements. “One of our values is ‘Have that dog in you,’” Stephanie shares. “We try to make our value statements reflect what it’s like to work at Nourish. Quite frankly, we might not be the best fit for everyone.”

Geoff points to a similar Ramp blog post about velocity that describes what people can expect if they join his team. “That creates a positive selection loop,” he says. “Write out things that are aligned to your values. People read it, and it resonates, and then they’re interested in potentially joining.”

In a competitive talent marketplace, how do you find people with that drive for fast execution? One of Ramp’s most successful programs for tech recruiting is an internship program. Every summer, Ramp hires about 50 interns. “Something I think is underappreciated is coachability,” says Geoff.

Balance momentum against risks

Ramp, Stripe, and Nourish all operate in regulated industries (finance and healthcare), so shipping fast is often met with a need for precision.

Stephanie shares how she helps her team make the right tradeoffs:

• Quantify known risks as much as possible to understand when speed is worthwhile.
• Find people who have worked through similar situations and can advise on guardrails to put in place.

With these practical measures, her team doesn’t live in fear of a “boogeyman out there” like a compliance person or potential audit.

Geoff adds it’s important to differentiate between critical and non-critical systems. For example, in the earliest iterations of the product, card authorization (approving or declining card transactions) was our lifeblood and something Ramp couldn’t get wrong. These critical systems operate with more checks and balances than other parts of the product.

There are also ways to fail that are a bit more “safe,” or at least have a lesser impact. “As you grow, it’s about putting the process in place so you can fail once, but not twice on the same thing,” says Geoff. “Because if you fail early on, the risk is much lower. Build a culture of postmortems, a culture of taking action on these things and learning.”

Identify processes that aren’t working

Many organizations add more processes as they grow, but too many processes come at the cost of speed and innovation.

At Stripe, Sophie recalls a few times that the company had processes that needed to exist, but weren’t really working for the people involved. She suggests that companies invite people going through the process to come up with something better. “That’s been a useful counterbalance,” she says. “Otherwise, people are spending time on a thing that’s not actually valuable.”

Stephanie says Nourish takes a similar approach to employee onboarding. New hires are asked if they encounter any friction points and if they have any recommendations. “They have the freshest set of eyes for what feels weird and what works well,” says Stephanie. “We’ve found that’s a really helpful signal because people are coming from different-sized companies, or a different set of processes with different people.”

Geoff cautions against having too many sub-teams and committees that dilute accountability. “If you put too much process, people will stop thinking for themselves,” he explains. “They'll be following the process versus just taking ownership and driving things through.” He points to engineering QA as an example. Instead of having a QA team to catch errors, Geoff expects engineers to be accountable for the quality of their code.

Larger companies put processes in place to maintain control, but at Ramp, “we will trade chaos for empowerment,” says Geoff.

Maintain velocity as you scale

Do startups have to sacrifice execution speed as they scale? Sophie says no. At Stripe, the user base is enormous and has very diverse use cases. She suggests forming small groups of great people—“tiny centers of excellence”—and letting them build something awesome for a small number of users.

Building a culture where work is done “in the open” is also key. At Ramp, this takes the form of looms, docs, weekly digests, and more. Geoff expects his team to proactively stay up to speed on what’s happening rather than expecting to be looped in. “We have a culture where the train is going to leave the station,” says Geoff, “You’re either on the train or you’re waving. But it is moving.”