Advice from Stripe’s Gloria Lin, Opendoor’s Ryan Johnson, and Notion’s Camille Ricketts
A Renaissance Collective x Bloomberg Beta Panel, Moderated by David King
At Renaissance Collective, many of our members are excited to join startups as early operators -- as the first marketing, first operations, or first business development hire. For smart generalists, joining something early lets you shape the product as its being created, and, as the team grows, you have outsized impact on the company culture. You get all the excitement of rolling up your sleeves and creating something alongside the founders in the earliest innings of the game.
However, the flip side of this potentially massive upside, is the outsized risk of failure. The earlier you join something, the less likely it is to be de-risked, and the more likely the trite-but-true “99% of startups fail” will haunt you.
So as a smart generalist who is considering joining something early, how do you sensibly evaluate the opportunity versus risks? How do you cast your lot with something great?
We decided to ask a few friends who joined successful startups early and developed their careers in a meaningful way as a result of those experiences. We are grateful to Gloria Lin, the first Product Manager at Stripe, Camille Ricketts, the first marketing hire at Notion, Ryan Johnson, the first employee at Opendoor, and David King, founder of Highlighter and early PM at Google, for sharing their experiences, perspectives, and candid advice with us.
For those of you who missed this event, we’re excited to share their advice with you here. Below are some of the most tactical takeaways from the evening -- on everything from how to connect with people in the startup to find a job before it’s even posted, what to dig into during your interview, to how to set yourself up for success from your very first day.
1. A warm intro puts you on the radar: “People can get you on the radar at a company you don’t know. Go to “see all connections” on LinkedIn to see if you have a warm connection. Explore that to the fullest extent. Even if it’s a second order connection, having a warm intro really helps.” - Camille
2. If you don’t have a warm intro, send a thoughtful cold email: “The secret here is to ping the person in the company that no one else is pinging. The number of people who ping the CEO is enormous. At Opendoor, I really appreciated the people who took the effort to write to me. One of my best hires of all time sent me a cold email – he connected to me and the idea of Opendoor in about 250 words. The worst cold emails are the ones that say, “Can I get some time?” - Ryan
3. Grab their attention by figuring out what they need. A good bet? Someone to manage internal tools: “There’s a big opportunity to connect with a company through the biz ops of internal tools. This is very similar to product management: internal tools are always needed and it’s a great foot in the door to solve really core problems. If you’re really excited about a company, try to imagine what kinds of internal tools they’ll need and document it.” - Ryan
4. Don’t be afraid to backchannel the founders: “When you’re interviewing, ask the founder a lot of questions, but also, don’t be afraid to backchannel. Ask founders for the names of people they would be comfortable with you talking to. Then go ask those people what insights they have into how to work with that person. I’ve found that the best question for back-channeling is: “what advice would you give me to have a successful relationship with this person? This positive framing lets the reference share something constructive, like ‘when this person gets stressed out, this is how to navigate it.’ The right type of founder will readily give you names of people to talk to -- and respect the fact that you want to understand them in a much fuller light.” -- Camille
5. Dig into the company culture by researching these 3 things:
How do they run all-hands? “Ask about the all-hands format – how often do they have an all-hands, what’s the cadence, how does Q&A work? Is there an upvote culture of Q&A? This will tell you how readily a CEO will share what people are actually interested in versus what he wants to communicate. You’re looking for whether you’ll have a lot of input and how transparent a culture is.” -- Camille
Who’s already at the company? “Look at the backgrounds of people who have already been hired. You can learn a lot about the culture that way.” – Ryan
How does the company communicate with its users? “The culture at Stripe was the thing that surprised me the most. Everything was so thoughtful and intentional. All the thinking was written down and shared across the company: “Here’s how we talk to users and here’s the voice we use.” It was incredible to see how thoughtful these founders were in thinking about things, seven layers deep.” - Gloria
6. To set yourself up for success once you’re at the company, gather as much information as you can from people both internally and externally.
“Set up 1:1s very quickly. If you don’t do it quickly, then it’s weird. Get it out of the way.” – Ryan
“Ask people, ‘what do you think I should be doing?’ That will tell you a lot, especially if your role is to help evolve the internal org.” – Gloria
“Ask to connect with end users and figure out how they feel about your company and product. When you start, you probably have the internal story that’s repeated by everyone who works in the company, but your customers probably perceive a different version of that. Get to the bottom of how they feel.” -- Camille
7. Hit the ground running. Pro tip: Document and suggest improvements for onboarding to add value on your first day:
“Onboarding for me was “this is where you sit.” Onboarding will not exist or it will be insufficient. This is a good opportunity for you to yield learning for them immediately and suggest an onboarding process.” – Camille
“At Google, I did a bunch of onboarding stuff and they asked me to document it. Their onboarding docs were really out of date because no one had updated them recently. My joining was an opportunity for them to change that. Onboarding documentation is a shareable artifact that helps every person in the org that hires someone. As the person who wrote the very good onboarding doc, you’re the person building bridges across the org.” – David King
8. If you want to be a founder and your goal is to maximize applicable learnings, join a hyper-growth startup:
“In retrospect, joining Stripe was so directly relevant for being a founder/CEO today. When I joined, I wanted to optimize for learning – it was early in my career and I was less than 5 years out from school so my thinking was, ‘these people are really great and super experienced.’ But when I look back, I learned so much. Things like: When you’re the CEO how do you establish trust with your team? How do you run internal comms effectively? How do you make sure everyone is direct with each other? How do you manage a situation when you have reports that are smarter than you and they want to take the product in a different direction that you deeply do not feel is the right direction -- but they have more domain expertise than you? How do you communicate all of that? I learned to navigate all of this at Stripe.” - Gloria
“When I was at First Round, I had the privilege of seeing a diverse set of companies. There were founders from Google and Facebook who had lots of domain expertise. Other founders were passionate first-time founders. I also saw founders who had been part of later stage hypergrowth startups previously. These were the founders who had an advantage because they could see around the corner. There comes a moment at startups where product design has to give way to organizational design and founders have to make the shift. People who have witnessed this transition directly, had a leg up.” - Camille
If you missed this event, and are curious to read more of the advice that was shared, our co-host Minn Kim, an investor at Bloomberg Beta, has an excellent write-up of the evening here. If you are working on something new and want someone to jam with, reach out to Minn here. And if you’d like to participate in future events like this, apply here to join us at Renaissance Collective.
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Special thanks to Minn Kim, James Cham, and the entire team at Bloomberg Beta for helping us grow this community and connecting us with their network of talented founders -- many of whom connected with smart generalists at this event! We are grateful to our speakers Gloria Lin, Ryan Johnson, Camille Ricketts, and David King for their insights, and to all those who read earlier drafts of this piece, including David King, Nadia Eldeib, and Henry Su.