January 21, 2020 / Blog

Tips on Breaking into Product Management from Dropbox PM Sheridan Clayborne

In this article, we’ll share the perspective of Sheridan Clayborne on how to get into product management with some great tips for aspiring product managers and some final words of advice.

Sheridan is a Product Manager at Dropbox in their new graduate program. He was the youngest African American to get into Northwestern at age 15. He loves start-ups and has raised over $5mil and done over $10mil in sales across his businesses.

Choosing the right major

Choosing a suitable major for product management early on is very important. For Sheridan that was majoring in computer science and economics. When working in product management it’s relatively useful to have a technical grasp of what’s going on especially when working for software companies. It also shows a general interest in software as a whole which may translate as a positive thing in interviews.

Internships and startup experience

Internships are useful in the sense that they teach you what you are interested in. Sheridan experienced this when he was working in JP Morgan. He realized that wealth management wasn’t for him. Talking with passionate founders trying to pitch how they’re gone change the world was fascinating. But what fascinated him even more was how these solutions and products were built internally. He was thinking, how can I build the same things myself?

Another thing with internships is that they help a lot with discovering a sector in which your interest lies and that you really enjoy. The software-as-a-service (SaaS) business was a sector Sheridan discovered. Consumer goods also appealed to him, but the growth in this sector was unpredictable in his view compared to a more “controlled” growth which the SAAS sector seemed to have.

With startups, the experience you can get can be compared a lot to product management. We can say that the best way to prepare to be a product manager is by just doing your own side project and going from idea to final, iterating on it and then building it out all based on feedback.


What has finance to do with product management you may wonder. Having an exposure into finance whether it is as a role or as a part of another role instills some discipline with numbers. As Sheridan views it, numbers can become a source of truth for a business if utilized in the right way.

Preparing for interviews

If we take the example of Sheridan again, reading up on interview preparation cannot be underestimated. When he was preparing for his interviews, the book “Cracking the Coding Interview” served him well even though it’s more geared to the software industry.

Finding other people who are also doing product management interviews is another great strategy here. The support of a practice partners where you can do mock interviews together can make all the difference.

There is this website Sheridan mentions called StellarPeers. It aims to help with product management mock interviews and acts like a community preparing product management professionals. Worth checking out.

Doing more of these mock interviews can completely change a perspective you had before. Sheridan’s tells us about when he realized that product management isn’t necessarily just being the idea guy in the room but more about being the execution person in the room. In his new perspective, product management was instead about:

  • Who’s the customer?
  • What are the different ideas can we can use to solve this problem?
  • What is the right problem?
  • How do we solve and track the problem?
  • How do we iterate it over time?

This changed his perspective into seeing product management as less ambiguous and that there was actually more structure to product management than he previously thought.

Applying for product management roles

When applying for these roles, a difference can be made between initially applying to roles and the choosing between offers later. In Sheridan’s case he was applying to any company willing to interview for PM positions. So initially sending as much semi-tailored resumes to companies is key here. He then starting hearing back from companies and that is when the latter phase of choosing and optimizing for different things starts.

Your choice depends on many factors but let’s mention three significant variables you can optimize for when choosing between product management roles you have been offered.

First your preferred industry, with Sheridan’s story this was SaaS businesses which he was more interested in than other sectors. Your preferred industry may be influenced by how you view that particular industry or where your proficiency lies. For example, a computer science graduate would be much more inclined to the software industry as a preferred choice due to his possessed proficiency.

Secondly, the product management team that you will be working with plays a big role in choosing between offers. If you are looking for ambitious people, flexibility and a supportive group that is something will help in refining and ultimately deciding which offer to go with.

Thirdly, the trade-off relationship between smaller companies and large organizations is relevant here. Larger organizations can be viewed as having a massive scale where products are pushed to hundreds of millions if not billions of users like in Microsoft, Google, Facebook etc. This in turn means they have a far more bureaucratic product management process than smaller companies. But these smaller companies make up for this fact in that things are built more quickly and product iterations are done faster. So, you are trading scale for more speed and less bureaucracy to cut through.

Final words of advice

Many people are concerned about not having a very technical background or a startup background. But as Sheridan has pointed out, companies are more open to a wide array of experiences. For example, you could have been part of a club where you were a leader or leadership organization, some hackathon where you work on a project, done some random side project or maybe done an art installation.

Any experience potentially counts as long as you can show that you can work with cross-functional people, as long as you can find a project that you’re passionate about and show how you actually went about going and executing on that with a wide array of people.

Something many candidates may miss that Sheridan realized is the importance of really think and empathize with the user as much as you possibly can. He recalls having this mindset of focusing more feature ideas and kind of like throwing it out there where it instead should have been much more around like what is the problem space, what is the actual story of the user that we’re trying to pitch for, what are the pain points that they are experiencing and how do we develop an experience around that versus: “Hey!, here are some different product ideas that would work for something like this”.

Finally, Sheridan reminds us that it’s also really a numbers game so you don’t have to worry when you apply to a bunch of places and you end up getting rejected. Instead, focus on applying to as many places as possible and then have a great time sorting through offers when you get them.

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