Evaluating early-stage startup opportunities as a Smart Generalist

A few weeks ago, our team at Bloomberg Beta collaborated with Jen Yip, founder of Renaissance Collective to bring together our communities of Smart Generalists, founders, and those on the cusp of their next career moves to hear from four early operators on what to consider when joining a startup early in a non-engineering role. Below are several tactical takeaways from our discussion.

A conversation with early operators (from left to right): David King (early Product Manager at Google), Gloria Lin (first Product Manager at Stripe), Ryan Johnson (first Operations at Opendoor), Camille Ricketts (first Marketing at Notion)

So you want to join a startup in a non-engineering role. You’re a fast learner and a resourceful problem solver. You have exceptional writing, communications, and interpersonal skills, and thrive on making decisions in ambiguous, cross-functional environments. However, it’s not always obvious how to evaluate generalist roles at fast growing startups, despite every growing organizations’ needs for versatile talent who can contribute across operations, business development, marketing, growth, customer support, sales, and more.

To help demystify these early-stage generalist startup roles, we asked four early operators — Gloria Lin, first Product Manager at Stripe; Ryan Johnson, first Operations hire at Opendoor; Camille Ricketts, first Marketing hire at Notion; and David King, early Product Manager at Google — who joined high-growth startups at important inflection points to share candid stories and tactical advice answering the following key questions.

1. How do I find great startup opportunities?
2. How do I navigate a role at an early stage startup?
3. What can I expect and how do I set myself up for success once I join an early-stage company?

1. Find opportunities through strong people networks

Many early-stage opportunities are loosely defined and may be marketed more often via word-of-mouth than on a traditional jobs page. As such, relationships will play a particularly important role in helping surface exciting early-stage opportunities, and access to these people networks will require resourcefulness around relationship building. Then, once you’ve identified the kinds of companies and the people you may be working with, the next step is to discover their needs and articulate the ways in which you can add the most value.

If you feel you don’t already have the personal and professional networks to access great early-stage startup opportunities, it’s never too late to cultivate them.

• Start with your first-degree connections. This includes close friends or former colleagues who may be at companies or in roles you are curious about. They will often have the greatest context for current priorities as well as the company culture set by leadership — this is particularly helpful at growing companies where early non-engineering roles will be ambiguously defined. Ask questions to figure out what challenges and problems are top of mind for them and be clear about where you see your value add. This makes it easier for them to help refer you or potentially hire you when the time is right. Ryan Johnson met Opendoor CEO Eric Wu when they were college roommates. As Ryan recalls, they always knew they wanted to work together, so when Eric approached Ryan about joining the team, Ryan ignored the oft-repeated advice to avoid working with friends. In retrospect, the trust that they’d already established laid the foundation for a great working relationship. Camille Ricketts had the good fortune of getting to know Notion’s CEO Ivan Zhao over the course of five years in her previous role at First Round Capital where the firm was an investor.
• Seek quality second-order connections. A seminal theory in sociology describes the power of weak ties in social networks, arguing that weak ties act as bridges to other networks, as well as to new and unique information (such as job openings!). As Gloria observed in her experience, “it was the weak connections who were actually the most helpful.” So don’t just start with the careers page. Instead, go to a company’s LinkedIn page, look at all the employees at that company, and seek a warm introduction opportunity, whether it’s from an alum from your university, a mutual friend, or friendly acquaintance. Meet people through shared hobbies and interests, communities (like Renaissance Collective!), and build relationships with a multi-year frame of mind.
• A thoughtful cold email goes a long way. Both Ryan and Camille hired candidates who reached out via cold, but carefully tailored, emails. These notes stood out because they included specifics reflecting the candidate’s understanding of the company’s challenges, keen observations about the business or product, and perhaps most importantly, ideas and suggestions for what else the company could consider to enhance the business. Another insider tip: don’t necessarily reach out to the founders or CEO because that person is likely extremely busy and just asking for their time is unlikely to elicit a response. Instead, find the person no one else is reaching out to and make the case that you have something valuable to offer.

“Get out of the job shopping and transacting mode, and more into people-meeting and learning mode.” — David King

2. Navigating an early operator role: Go where you are needed

Early stage startups are messy and roles are loosely defined. If you join something early, you should expect to operate under a lot of ambiguity, where your day-to-day priorities could shift rapidly. To determine where you will be able to add the most value and maximize your chances of success as an early non-engineering hire, consider the following:

• Optimize for company growth, not role titles. For companies at very earliest stages, generalist roles may look like managing a hodgepodge of finance, legal, vendor and contractor management, recruiting, business development, and office needs. However, growth creates opportunities (more on that here), and being in an early generalist role could set you up to build out a variety of functions for the org — from Business Operations, Product Management, Community Manager, Quality Assurance, Product Marketing, Customer Success, and others — just waiting for someone to take on. For example, Ryan started out as a Business Operations generalist, which positioned him well to build out and manage a new product team focused on new mortgages.
• Don’t underestimate your generalist skills. Gloria eschewed the commonly held belief that Product Managers should have traditional Computer Science or other technical backgrounds. Stripe began with the belief that engineers should manage their own products because of their deep understanding of the technical underpinnings. They were famously slow to hire, and it took Stripe five years before they looked for their first Product Manager. However, by the time Gloria joined, she saw a large chasm between user facing teams, like sales and support, and the engineering teams. So while it was important that she could talk enough to deeply understand the problem space they were working in, she defined the “the hallmarks of a great product manager [as being] an amazing communicator [and] fantastic storyteller…to define what are we doing and why and for whom.”
• Anticipate what roles don’t yet exist and seek to fulfill them. As a company grows, they will inevitably need certain new functions. Check a startup’s LinkedIn page, its employees, and what functions exist today. Then consider what roles they may need in the near future, such as a full-time recruiter or product manager. Another insider tip: an underrated but big opportunity is to build internal tools. These include business intelligence tools to track revenue, HR internal systems, or a CRM. Building and managing these tools are a close analog to being a Product Manager, and is often a great foot in the door to solve core problems inside an organization.

3. Set yourself up for success by learning to adapt to rapid change

An early-stage opportunity within a growing organization offers a lot of potential to have a positive impact on the company’s evolution and to grow with the company. As Camille notes, “every single hire under 100 people has profound impact on the culture and in shaping the [company’s] direction.”

As a Smart Generalist at an early-stage company, your ability to adapt to rapid change will be critical to helping the company drive towards a common goal (not to mention for keeping yourself sane). Even for someone like Camille, who had seen many early-stage companies up close during her First Round days, she found her first nine months at Notion were still a shock in terms of pace and amount of change. Her advice: Anticipate the delta between what you expect and how things may change. “Then also just know that [change] is going to be an inevitability and that you don’t need to hold on to what you thought was going to happen until your knuckles are white.”

As you’re adapting to your new environment, note the differences between expectations and reality. Write down the basics of what you expected and what the reality turned out to be. Set up 1:1s with peers across the organization to collect feedback on what’s working and what needs to change with questions like:

• What did you expect and how was your onboarding experience?
• How do you think we can improve our all-hands (frequency, format)?
• What is our decision-making process around a business strategy?
• What is the culture around feedback? How is it given and shared?

Your fresh perspective will be helpful to a startup because you can take those observations to document a new process or suggest an improvement in existing practices — from new hire onboarding to internal documentation to product strategy. As a Smart Generalist, you may even find yourself in a management position before you anticipated, in which case your observations will be important artifacts to build and inform new strategies and processes that evolve the organization. So take Ryan’s advice and “take advantage of being a rookie.”

Being a strong generalist is a superpower

At Bloomberg Beta, we work with early-stage startups where success often comes from bringing the right group of talented individuals together to solve big, interesting problems. Smart Generalists are a critical addition to such growing teams at early-stage startups, and we believe there is no shortage of ways they can have impact. Ultimately, we hope these takeaways will help you find the startup opportunities relevant to your skills, understand what to expect in the day-to-day of an early non-engineering role, and identify ways to effect change within fast growing organizations.

Special thanks to Jen at Renaissance Collective for bringing together a thriving community of Smart Generalists (learn more and apply to join here!); to our speakers Gloria Lin, Ryan Johnson, Camille Ricketts, and David King for their insights; and to all those who read earlier drafts, including Jen, Alizeh Iqbal, Mason Tang, and Nadia. You can also find me on Twitter if you want to learn more about early-stage opportunities or are working on something new yourself.