What it’s like to learn product at a small startup

Photo by Death to Stock

Recently I’ve talked to a lot of people looking to get their first product job at a startup. After two years learning product at a small startup, I want to shed some light on what it’s like to help people decide the best place to start.

I joined ReadMe as the first employee. The company had just finished Y Combinator and raised a seed round. We had enthusiastic early customers and a new product that helped developers create API documentation. Since then our team has grown to ten (still tiny!), we’ve quadrupled our customers, and we’re about to launch a second product.

As we’ve grown my role has evolved. In the beginning, I focused on supporting our customers and doing whatever it took to help the product grow. Since then I’ve introduced a more formal product development process and helped to shape product direction.

At this stage, the role of a PM varies a lot by company. We’re a startup with only 10 people, so my experience won’t necessarily reflect what it’s like at a company with 200 people, or even a different 10. However, here are a few things that are fundamentally different about product at a small company:


  • Ownership & Accountability: Ownership over a product is both a big responsibility and opportunity. At a large company, a PM will likely have a series of experienced product leaders shaping product direction. At a startup, you are the one shaping the direction. You have the opportunity to make big changes (hopefully improvements!) in the product, but you also take responsibility for any mistakes.
  • Scope: Where at large companies there are many PMs who focus of individual features, at a startup you’re charged with thinking more broadly about the whole product. This means planning for more than one feature simultaneously and considering things that affect the whole product. For example, one of my first projects at ReadMe was to build better community features for developer hubs but I also needed to determine how we could adjust our pricing plans to target customers that would benefit from these changes.
  • Hands on experience: At a startup, you’re the one putting in the work to drive the whole process. For a certain feature I often do everything from leading user interviews to planning engineering time to developing launch materials. When we redesigned our onboarding, I talked to dozens of users to find drop-off points, user-tested wireframes, and rolled out a new email campaign. Handling projects this way lets you develop experience in a lot of different areas quickly, where at a larger company these might be divided into different jobs.
  • Opportunity to try lots of things, and fail: Since there’s no prescribed way to do your job, you have the opportunity to test out different methods and to try things that might not work. Everyone is generally collaborating on the best solution and its okay to admit failure as long as you keep trying.
  • Work directly with customers and engineers: At a larger company, the role of communicating between customers and engineering might be split between user research, project management, or a tech lead. At a startup, you are the one doing the research, defining the problem, and presenting data and information to your team. This requires you to reframe things for the correct audience and make sure everyone has a good level of comprehension.


  • Defining your role: In a scrappy startup environment everyone is doing whatever they can to reach the next goal. It can be difficult to balance helping the team and focusing on learning product. In a very small team, being a PM can mean you’re the one who volunteers first for the jobs that a PM would do at a larger organization. As the team grows you’ll need to be explicit about the role you want and show you’ve done a good job in the past. Because PM roles can be flexible, it requires some research to even know what the role should be. I found it really helpful to talk to people with more experience and to read the advice of veterans like Ellen Chisa and Ken Norton.
  • Creating organization: While days and weeks at a big company are often structured to hit specific product goals, startups can easily fall off schedule putting out fires. Many people who want to become PMs are organized by nature, and this can be frustrating. On my team, I’ve taken it upon myself to create organization, from engineering schedules to launch plans. As a PM on a small team, you’re not only in charge of creating a plan to fix a problem but also for making sure people stick to it. Understanding how much organization is necessary to get things done, but without getting in the way, is an important skill.
  • Limited resources: Every company struggles with limited resources but at a startup this problem can be even more severe. Some of your best ideas won’t see the light of day. PM’s at startups need to understand what company-wide priorities are and be very diligent with time.
  • Mentorship and personal growth: Startups have fewer people and often many fewer product people. Unlike companies with a formal product chain of command, there’s often not many in-house mentors to look to for product or career advice. PMs at small companies need to put in the work to identify mentors and communities that can help them improve their skills. I’ve made great connections in the Women in Product and Products that Count communities both online and in-person.
  • Defining success: This has been the hardest part of working at a startup for me. Unlike big companies, there are no career ladders and it can be difficult to know how you are doing both for your company and in your career. When you are working on the whole product, it can be hard to isolate metrics for each feature to judge success. One way I’ve found to counteract this is to identify key customers to interview before and after a new feature to see if it has improved their use case. For personal success, I’ve asked more experienced PM’s for guidance on which skills to focus on and looked at job postings for jobs I’d like to have in the next 2 or 5 years.

Learning to be a PM at a startup is challenging and rewarding. You’re fully immersed in the business and directly impacted by the results. It can be a great way to gain experience quickly but comes with trade-offs. Feel free to get in touch at hi@ashleychang.com if you’d like to talk more!

What benefits and drawbacks have you seen working in PM at a startup? Do you have any questions about learning PM at a startup? Comment with your response!

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