Read This Before Joining as Employee 1 to 20 at a Startup

Read This Before Joining as Employee 1 to 20 at a Startup

Should I work for a startup? Before deciding, find out here the best employee tactics to survive in a starting business and thrive as an early employee.

It’s week six in your new job at a bootstrapped startup, and the founder asks you: “Create a prototype of our software to share with investors. We don’t have a company name yet. And I need it in two days.” If this sounds familiar, chances are you’ve been an early employee at a startup. If this is your precise scenario, you’re Stacy La, Clover Health’s Director of Design.

When La first started with Clover Health, it was just the founders, head of product and a data scientist. She was its first designer and the company hadn’t raised any money. Now she leads an eight-person design team, Clover is 500+ people-strong and the startup has raised over $425M. Though La was a seasoned design leader (Yammer, Microsoft) before Clover Health, it was her first time as a very early employee forged in the crucible of a fast-scaling company.

In this exclusive interview, La reduces nearly every motion of an early employee to flexing one of two muscles: ruthless prioritization and high-return troubleshooting. For the former, she outlines a sequence of time management milestones to expect as an early employee in year one. For the latter, La asserts that every challenge must produce double the return in takeaways — and gives examples of that principle in action.

Ruthless Prioritization as a Timeline

From the list-making apps like Asana and Things 3 to hyperfast email like Superhuman, there are many tools that can help generate greater efficiency. Then there are philosophies from productivity aces like Getting Things Done’s David Allen or Lifehacker’s Gina Trapani. All these resources can be valuable for the overworked, under-resourced early employee, but according to La, time management operates as a unique frequency for a startup’s first employees.

“At the start, it was fun taking the leap and deciding to get involved as an early employee. I was back together with people I had worked well with before,” says La. “But then it got daunting very quickly. The magnitude of the task ahead hit at once: my hybrid doer/leader role for a functional area, my learning curve in the health insurance space, and all the opportunities that Clover could go after in the market. Suddenly, spinning up felt more dizzying than galvanizing.”

Early employees: when it comes to time management, stack your priorities in two-week themes. That way you can balance actionability and flexibility.

With the support of Clover’s founders, La hit her stride when she zoomed out not only on her goals for Design at Clover, but also for herself as an early employee. “When joining a later-stage company, your role and career path are more defined,” says La. “On the other hand, for a first employee in an area like engineering or design, you must, of course, focus on shipping your part of the product. But there are also responsibilities that aren’t immediately apparent, like being the leader of a team — even if it’s just you at the moment. How you do the work — especially alongside other functional heads — sets the standard for how your team will integrate and run. Self development as a leader beyond your function at the company is also a responsibility. When the ladder rung above you is the founder, your goal is less to replace that person and more to come into your own. This requires original thought in defining the kind of leader you want to be and career that you want to create.”

When La speaks about how she discovered and chipped away at those responsibilities, she suggests a timeline more than tips. Here’s a sequence of inflection points that served La and can help you, as an early employee, gut-check your development approach to product, team and career:

Map two-week themes for the first six months. Context-switching is a killer for everyone — especially for early employees who have to wear multiple hats. You have to be versatile, but focused. “Early employees, like founders, must constantly operate at a balance of breadth and depth. I found the best unit of time to both efficiently execute and accrue a sufficient level of expertise on any key task was about two weeks,” says La. “For example, when vetting design agencies, all my planning, research, meetings, evaluation and decisions happened in a two-week span. Prioritizing biweekly themes creates enough momentum to create real value in a particular area of the business, but not so much as to cause a terrible setback if the intended results aren’t achieved.”

La stacked priorities based on the constraints facing the business at the outset. “The nice thing about being there at the start is that your priorities are very clear, because the constraints are numerous and looming. The most pressing must be addressed or the others won’t matter because you’ll be out of business,” says La. “For example, we’re driven by CMS [Centers for Medicare & Medicaid Services] deadlines. We had to be ready for open enrollment, which is October through December, and we had to have a brand and website. That needed to be in place before we could even think about hiring user researchers or developing a design system. Two-week themes are flexible enough that I could swap them modularly as business needs changed, if needed — and compact enough that I was too busy to waste time thinking of opportunity cost once I decided to embark on one. Focus and flexibility made this approach work for my first six months.”

Standardize how you triage your time by six months. As Clover grew, La adopted a practice that her mentor, Airbnb’s Head of Design Alex Schleifer (introduced to her by Whitnie Narcisse as part of First Round’s mentorship program), calls “eyes on, hands on, horizon.”

“It’s a practical way to triage my time. ‘Eyes on’ is work that I don’t need to do, but need to be informed about, such as designers’ progress on projects or design requests from the org. ‘Hands on’ are actions that I need to work on independently. That could be meeting with candidates or developing the design team’s OKRs, for example,” says La. “‘Horizon’ is a category of themes and developments that are a month to six months out. It’s about to get on our team’s radar, but not yet on mine. Right now, that’s our design system, for example. This practice helps me get through to-dos and delegate. I do it on my own at the beginning of every week but at Airbnb Design’s scale, Alex does this exercise daily with a member of his staff. He emphasized to me that constant prioritization — the act of choosing to work on the right thing at the right time, over and over again — is the thing that will make or break a business. I’m now a lot more diligent about what I spend my time on, and the cost and ROI of those choices.”

Splitting one’s time into these buckets creates processes — new ways that information flows through an organization. While this creates predictability, it can also fill up one’s calendar. “As the number of stakeholders increase, there’s a tendency to build in more process. So another great tip that Alex [Schleifer] gave me is: ‘Don’t add process unless it removes a meeting,” says La. “That rule of thumb keeps you honest. When we started weekly Design Reviews, our goal was to give technology leadership visibility at key project milestones, and to push faster decision-making while shipping high quality solutions. Adding Design Review into our design process eliminated 5+ individual context-sharing and sign-off meetings.”

Stacy La at Clover Health's office in San Francisco

Pivot from product design to org design at month 9 to 12. Clover Health grew incredibly fast — in about two and half years its headcount went from five to 500. Given that, La began shifting her focus from design work to growing a design team within nine months of joining. Not only was she creating what the product was to become, but also how it was going to be built.

“At about nine months, most my time was spent on recruiting and hiring, which was a shift out of my comfort zone. As an introvert, I noticed a change when the day held more coffee chats than independent work. When I wasn’t meeting people, I was drafting job descriptions, not just designing the product,” says La. “This isn’t atypical for any individual contributor who becomes a manager. However, as an early employee, a smooth transition at this moment is critical because it has a lasting effect on what the team will become — and often requires a founder’s attention. Kris [Gale, Clover Health’s co-founder] helped me realize that I was doing organizational design. I had to grow and structure a team that could get it all done.”

The key output in this time period is called cathartic documentation. “When a company grows that quickly after you’ve joined, you naturally get institutional knowledge that’s layers deep. Of course, this know-how shouldn’t be organized chronologically, but by utility. Luckily, an early employee has the built-in perspective to arrange this knowledge — and I’d argue the need, not just the ability,” says La. “It was a release to get it all down and scale what I’d learned to the rest of the team. This was, and continues to be, crucial for building out our team, onboarding new design hires, the design review process and more. Growing quickly, I didn’t want the team to constantly reinvent the wheel.”

Scaling herself by documenting her design know-how gave her the bandwidth to help the company hire in a more intentional way. “When you have 15 people starting every week for 3 months you have to be extremely thoughtful about the hiring infrastructure you have in place. Communication gets exponentially complex and difficult as you grow, so we had to be conscious of who we were hiring and why,” says La. “It took months of discussing and interviewing candidates, articulating our mission and thinking about how we wanted to structure the team. At the beginning I didn’t know how to pitch health insurance in a compelling way, and we didn’t have a product to show. What we did have is an awesome mission. I internalized our mission and the potential impact for design in the industry. In expressing it, I realized just how much I believed in what we were trying to accomplish. After that it was easy to decipher which design candidates had similar beliefs and interests.”

The demands of a startup are dizzying. To anchor yourself, you must schedule time to write things down.

Troubleshooting to Double the Learning

Any professional needs to learn how to problem-solve — but early employees have to harvest more from each challenge faced. In fact, according to La, as an early employee, you must mine at least two actionable takeaways for every challenge faced. If you aren’t hitting at least that level of learning, you aren’t 1) tackling big enough challenges for the business or 2) reflecting on and extracting enough from each task. Here are a few examples to illustrate some of La’s high-yield rate of learning as an early employee at Clover Health.


It’s no surprise that early employees are drinking from a fire hose — and often alone. The isolation can be palpable with few or no other colleagues tackling the same swath of challenges. La found camaraderie externally early on to counter her independence — and isolation — as Clover’s first designer. “When you’re a first employee, you need peers. So one of my best moves was finding and reviving a dormant meetup. When I discovered it, there were about 80 members, they were looking for a new organizer, and there were no events scheduled. I took it over, and now the Design for Healthcare meetup has over 1,500 members.”

“It was great on the branding side for both Clover and myself. My team was still forming and I hadn’t worked in healthcare before, so developing a supportive design community was helpful,” says La. “It assisted in ways that I didn’t initially expect, and came to appreciate later on: creation of a community. It's great for professional development and finding connections in our work since not many designers have a healthcare background, and healthcare startups don't have huge design teams.”

Beyond the meetup, La sought additional resources to get the camaraderie and know-how she needed to do her job — and Clover’s co-founders stepped in. “I needed help and wanted to talk to other designers. I also didn’t know much about healthcare. Vivek [Garipalli] had healthcare experience and connected me to people at other healthcare startups, like Oscar and Flatiron. And Kris [Gale] introduced me to designers and tech leaders in San Francisco,” says La. “They didn’t do more than just set up calls. Their style is not to tell me how to get the answers but to give me access to smart people for 30-minute calls at a time. I drove a lot of these conversations because I knew what things I was weak in and what I wanted to know.”

The second benefit of these “learning calls” was how it redistributed the founders’ rolodex throughout the organization. Creating more highly-networked nodes at a company can groom leaders faster at startups at their earliest stages. “Kris [Gale] introduced me to Michael Margolis, UX Research Partner at Google Ventures, who’s an incredible resource for me when it comes to user research,” says La. “I reach out to him regularly as I’m building a new user research function or look for referrals for candidates. To have access to that knowledge and expertise when you don't have it in-house is the next best thing.”


A defining moment for La was how she learned to build her team. “One of the mistakes I made as a manager is not hiring the right people. When they didn’t evolve with the company and team, I didn’t find a way to let them go sooner,” says La. “This isn’t an unusual experience for a new manager. But, as an early employee, it was unique in that Kris [Gale, Clover’s co-founder] was involved. He was invested in choosing people who’d help us define the company.”

But La didn’t realize then that, while Gale wanted to hire great new team members, the person he wanted to empower through the process was La. “Regarding the bad hire, Kris saw the writing on the wall before me, but he didn’t say anything. He’d ask me questions: ‘What’s your plan of action?’ or ‘Are you sure?’ but never told me what to do,” says La. “It was more than just a license to fail or a psychological safety net. It was not cheating me out of the depth of that experience. He showed trust, but more so, let me own the decision and hone my own instinct for hiring and firing. Only when I let the person go, did he say he agreed and we debriefed, asking me what I learned and how I was going to treat this situation differently later.”

Ever since those early days, La has been able to spot performance problems and address them more swiftly. If it’s needed, she’ll fire faster — speed, she’s learned, is both for the team’s and the person-in-question’s benefit. “Being able to handle that experience from end-to-end gives me personal, embedded knowledge that I own and can reference. And not just for the next time someone may need to get fired, but for how I hire,” says La. “That experience alone has changed the way I've interviewed. For example, now I put a premium on asking questions that assess their self-awareness and understanding of their strengths and weaknesses. I also never skip doing reference calls or back channels for every new hire. It’s altered how I approach my system for performance plans. For example, I’ve gotten more rigorous on explicit expectations to make sure feedback is tied to that versus subjective emotions. That’s an incredible ripple effect. If a founder can do something like that for an early employee that takes a leadership role, they’ve gotten a lot of ROI from one experience.”

When I say it’s a trial by fire for first employees, it’s also in a way you may not consider. The first person they fire will have an outsized impact on that team’s future.

Bringing It All Together

For La, choosing to be an early employee has been one of the most transformative experiences of her career. To excel as an early employee requires mastering two key acts. The first is prioritization through time management. It’s critical to find the right increment of time to cover the field but not spread yourself too thin, while also ensuring you’re well-versed, but not a specialist. To hit a balance of breadth and depth efficiently, La recommends a two-week sprints for the first six or so months to achieve maximum flexibility and focus. By month six, standardize how you triage, such as the “eyes-on, hands-on, horizon” framework. Between month 9 and 12, you should be migrating your focus from building your part of the product to your corner of the organization. Embark on a cathartic documentation to jumpstart this transition. The second critical skill for an early employee is troubleshooting. Given the velocity, you must extract two actionable takeaways from every challenge. Your rate of learning is your currency.

“Joining a company as an early employee has all the benefits you’d expect — equity, leading an entire function, working closely with founders, and defining your role. But the one that hits home for me is how I’ve defined my personal philosophy on design,” says La. “Since the start, Kris [Gale, Clover’s co-founder] reinforced the importance of being clear on my vision. I came in with a very different perspective — and that changed because I had to find the answers for myself as the first design employee. I always had the support of the founding team, but that early-employee environment is transformative. You don’t get that in a three-year stint at a Google or Facebook. It happens at the beginning.”

Photography by Bonnie Rae Mills.