Will Doolittle is Vice President of Product at Humu, a software startup seeking to make work better through behavioral science and machine learning. He has previously led product teams at Freckle (acquired by Renaissance Learning), Google, Inkling, and SuccessFactors (acquired by SAP). He has a BA in Philosophy from Oberlin College and an MBA from UC Berkeley’s Haas School of Business.
First of all, what even is product management?
Great question, let’s actually start with what it isn’t. First, despite having “management” in the title, It’s not about managing people — most PMs don’t have any direct reports. It’s also not the same as project management, which is planning and executing detailed schedules for teams — although some of that might come into play as part of the product management role.
Product management is really about doing whatever it takes to make your customers happy by shipping a great product. What that means will vary a lot from company to company and product to product, but in the software business you’re usually splitting your time between working with customers (and customer-facing roles like sales and customer support) and working with internal roles (like engineers, designers, marketers, and content creators). PMs gain a deep understanding of what their customers need, rally their team to align on the best solution, align product plans to business strategy, and make the tough prioritization decisions when tradeoffs are necessary.
What do you love about Product Management? What is hard about it?
I love the variety of the work, and the fact that I get to collaborate with people in many different roles every day. This is a great job for people with lots of interests and a short attention span (ha!). You get to be creative when defining solutions, but it’s also great fun to elicit other people’s creative solutions. And of course it’s super satisfying to launch a product that addresses a real need that people have.
The hardest part is not being able to do everything at once. There are a thousand things that have to happen to launch a compelling product, and as a PM you often have to make the calls on what gets dropped to make way for the more important work. What’s worse, you may not have explicit authority to make those calls; you’re managing through influence, so you have to have solid arguments and be very persuasive to get everyone else on board.
What skills does someone need to have in order to be successful in an entry-level Product Management role?
Top of the list is communication. Written, verbal, one-on-one, group settings, public events — PMs have to do it all, and they have to get everyone aligned and pulling in the same direction.
PMs also have to have deep empathy, paired with curiosity. This is most often invoked when talking to customers: you have to really understand their situation and probe on what kind of solution would meet their real needs, which may or may not be exactly what they’re asking for. It also comes into play when talking with internal teams, like helping engineers think through how to craft innovative yet feasible technical solutions.
It also helps to be a compulsive problem-solver. You’ll be tested every day with new and complex puzzles that need fresh approaches.
Based on your experience in EdTech, why might a teacher make an excellent Product Manager?
In any kind of tech company, PMs traditionally come to the role with either domain expertise or technical expertise. So in EdTech, a teacher obviously has that domain expertise! Teachers are also typically great communicators, and are empathetic…they’ll just need to put themselves in their customers’ shoes, instead of their students’ shoes.
To work effectively with the internal technical teams, it helps a lot to be a power user of current educational technology. The more experience teachers have as users of EdTech solutions, the better. Combining that industry knowledge with classroom experience can make a teacher a huge asset to a team that would otherwise fall into traps that the competition knows to avoid.
When you’re trying to fill an entry-level Product Management role, what do you screen for in resumes and cover letters?
I’d favor people with teaching experience plus some other relevant qualification, like a degree, certificate, or experience in technology, business, or design. Personally, I like hiring people with varied experience: it shows curiosity, intellectual agility, and a willingness to take on new challenges; a PM that brings experience in another field or domain can help trigger additional insights when the team falls into a rut. Even completing an online boot camp in data science or web design will help you stand out from the pack.
Like any job application, it’s also super important to express why this role and why this team. Cover letters that state these two things clearly and concisely will generally go to the top of the stack. Enthusiasm goes a long way! (But keep it brief — hiring managers are always pressed for time.)
What would compel you to advance a former teacher to the final interview rounds, even if their whole professional career has been in the classroom?
Assuming you’re through the screening process and get that initial conversation, and aside from reinforcing all the stuff we talked about already, I’d say the most important thing is to ask a lot of questions. Again, show that enthusiasm and curiosity. Ask the interviewer things like, what’s the most important measure of success for people in this role? What kind of data and input does the team use to make product decisions? What challenges lie ahead? What is the team’s superpower? Even if you don’t get the job, every interview is a chance to learn things that can be applied in future interviews and roles.
What do you see as “red flags” that tell you someone would not be a good fit for Product Management?
The biggest red flags for me are expressing the wrong reasons to want to be a PM, and having unrealistic expectations for what the role is like. Some people may have heard that it’s like being the “CEO of a product” and want that level of control, perhaps because others have been “doing it all wrong.” The interest has to start with wanting to do good for the customers and for students, and you have to bring a collaborative spirit that will bring out the best in your teammates. An inflated ego or lofty demands will just set you up for failure.
What other advice would you give to someone who is hoping to move from teaching to product management?
Dive into sites that talk about the business of EdTech and read as much as you can. General news and tech sites like LinkedIn and TechCrunch also surface lots of EdTech news. It may seem like gibberish at first, but knowing which edtech startups are getting funding, getting acquired, going public, or just trending up or down will enable you to have much more productive conversations with product management leaders.
If Product Management sounds awesome to you…
You’re right — it is awesome! A caveat, though:
You might have noticed that I didn’t include Product Management in this EdTech Career Path breakdown. Why not? Well, my goal with that resource was to emphasize jobs that do not require technical experience and are natural pivots from the classroom. While I find Product Management super rewarding and I think that teachers can make excellent Product Managers, it is candidly very competitive to secure entry-level PM positions without exposure to related disciplines.
Still into it? I see a few viable paths:
Embrace your inner student.
Sign up for a bootcamp to earn credentials in product management, UX design, and/or software engineering. This will beef up your resumé and give you a better sense of whether or not the role would be a good fit. Some options to explore:
- Coursera offers a highly-related Product Management specialization through the University of Virginia. It’s self-paced and includes 4 separate courses to ground you in the fundamentals.
- General Assembly offers everything from free workshops to full-time, immersive courses in software engineering and UX design — working knowledge of these fields will make you an infinitely more effective Product Manager and show hiring managers you’re taking the career switch seriously.
Consider joining an EdTech startup in a non-PM role first.
Note that internal pivots are often easier at smaller companies where employees wear lots of hats. For example, when I joined a startup as a Curriculum Designer, I was encouraged to contribute ideas about how the product should work and execute on those ideas with support from the Product Team. When an Associate Product Manager position opened up, I was a natural fit because I was already doing parts of the job.
While there are certainly no guarantees here, you can position yourself well for a switch into Product Management by internalizing users’ pain points and brainstorming creative solutions, regardless of your formal job title. Some of the best Product Managers start as Customer Support Representatives or Account Managers because they are intimately familiar with the product and its limitations.
Do the job to get the job.
If you have the time and inclination, try creating your own “product” as a side hustle. For example, if you create, market, and sell your own curricular materials to other teachers, this is absolutely something you should put on your resumé. It shows hiring managers that you’re already thinking through many of the problems that Product Managers encounter each day!