How I Transitioned from Startup Founder to Product Manager
Last year, I shifted my startup TheShareWay to a side business and was on the job hunt. As the CEO of TheShareWay, I enjoyed figuring out our users’ problems, building a product that improved their lives, and seeing the “aha” moments on their faces. Naturally, I applied for Product Manager roles.
I couldn’t find any resources on transitioning from a startup founder to a product manager. Most articles I found were on why product managers would make good startup CEOs and how to transition from an engineer or a consultant to a product manager.
I spent two and a half months job hunting and eventually joined Oscar Health as a product manager. Here are some things I learned on my path to becoming a product manager. If you enjoyed this, also read Part II on how to succeed at your first product manager job.
Give yourself a PM crash course.
As a startup founder, I learned how to build products by doing it. I was not in an environment where I could pick up product frameworks from colleagues.
During interviews, I stumbled on questions like how do you see the role of design and walk me through the stages of a product you built. This is mainly because I didn’t have the vocabulary.
I’d say something along the lines of, “I interviewed users to figure out what they need. Then, I would share the findings with my co-founder. We’d come up with a design together, prototype it, test it, and iterate.”
I didn’t pepper my responses with keywords like discovery, requirements gathering, prioritize needs, sprint, stakeholders, etc.
To learn the vocabulary, I went to product events, read books, and asked my friends on how I could better answer these questions. These all helped me convey my work in a manner that industry professionals would understand.
For books, I’d recommend Cracking the PM Interview, Inspired, The Design of Everyday Things, Sprint, and Teresa Torres’s essays. For events, Product School’s weekly events in New York City were helpful.
Most people have not been entrepreneurs before and won’t get you. Hustle to find companies and people who value your experience.
Just as how venture capitalists pattern match and fund founders who look and speak like them, some level of pattern matching also exists in hiring. Interviewers like to hire people with similar backgrounds to successful employees at their firms.
Pattern matching in hiring is a disadvantage for founders because very few employees are former founders.
Don’t get hung up with the interviewers who just don’t get you. Move on. You’ll find people who get you.
Startups will value your experiences a lot more than larger companies.
Startups need people who can wear multiple hats, which is something you have demonstrated as a startup founder.
Leverage your industry knowledge from your startup.
Product managers need to be the voice of their users. Because my startup served nonprofits, I landed a lot of interviews with companies that built nonprofit products.
Find roles that are more ambiguous or seeking product-market fit experiences.
After I started at Oscar Health, my manager told me that they hired me specifically because the product area I was owning had more ambiguity. They wanted someone with product-market fit experience and who wouldn’t be fazed by uncertainty.
Your meaty stories might span years of work since you were wearing multiple hats as a founder.
While product managers at companies dedicate most of their time to seeing a full product launch go through, startup founders work on sales, marketing, hiring, and many more things.
Your story might come from experiments that spanned a whole year or two because you had to juggle many responsibilities. For example, I had a landing page redesign six months after we launched. Then, there was a one year gap before we further optimized the landing page funnel. In that year, I had split up with my co-founder and found a second co-founder, who basically rebuilt the whole site.
You don’t have to include all the gory details of co-founder breakups and pivots. Focus on the experiment, the funnel, and the conversion lift you achieved.
Know how to answer: “You don’t have formal training” and “We are looking for people with more experience”.
Because you come from an untraditional background, these questions are going to come up. I have three tips:
- Focus on asking them what skill sets they are looking for and back up those skill sets with experiences you’ve had.
- Talk about how you had the best kind of training by building a product from scratch. If your numbers look great, you can even add in user numbers and growth rates.
- Most importantly, respond with confidence.
Believe that you have a lot to offer!
During my interviews, I projected a lot of confidence, but deep down, I didn’t know if I was good enough because I hadn’t had the opportunity to benchmark myself against my peers.
Now that I have worked in product management in a corporate setting, I can confidently say that you do have a lot to offer:
You will stand out on being scrappy.
This one time at Oscar, instead of building a feature, I suggested using spreadsheets and mail merge to validate first. The experiment pointed to no build. We saved weeks of engineering time.
I was surprised when my colleagues complimented me on my scrappiness. I only had one engineer at TheShareWay. To me, hacking together solutions without code is normal.
You deeply understand what making something people want means.
As startup founders, we all have made wrong assumptions around what users want. We have felt these mistakes deeply because they have cost months of runway.
For TheShareWay, I once spent three months building a product that never got used. That was 17 percent of my runway. I have vowed to never make that mistake again.
Some key lessons that I will always take with me are 1) don’t build things that people haven’t demonstrated that they want, 2) build painkiller solutions not vitamins, and 3) your product has to be 10x better for people to switch.
At my job, I have noticed my ability to confidently hold my ground on why certain solutions won’t work. This confidence comes from my failures.
Switching careers is never easy. I hope these tips can help you be more successful in your job search. Also, see part II on how to succeed at your first product manager job.
