Interview With Jesse Herlitz: The Day To Day Life of Being VP of Product at Flow

jesse-herlitz-yesinsights product management

Jesse Herlitz is currently the VP of Product of at Flow. I had the honor to do a very detailed Q&A with Jesse on the day to day life of being a VP of Product at one of the best project management SaaS tool companies. Jesse previously was a Product Designer at Simple Finance and worked intensively on product at Starbucks before that. Enjoy!

Wilson: Hey Jesse! Thanks for doing the interview. Could you tell me a little bit about yourself and how you got involved in Product? What is a day in life for a VP of product?

Jesse: I can’t say what it’s like for others, but I can tell you what it’s like for. I usually wake up, and check Catch Up in Flow to see what was worked on while I was sleeping in other time zones. Most of my morning is spent reviewing designs and giving feedback. I also check in with our Android Developers who are in Europe so my time to communicate with them is limited. After overseas remote people are taken care of I’ll take a look and see if anyone in North America needs answers on anything or a decision made. After everyone is taken care of I’ll typically block out a few hours on my calendar and put Flow into Focus mode to do some sketching of whatever feature on our roadmap needs to get designed next. After that I’ll typically check out our analytics to see how the product is performing, and respond to people’s questions in our feedback forum. Unless I’m focusing, there’s usually a healthy amount of back and forth with everyone on the team most of the day. Questions come in often, and I try to answer them as quickly as possible to keep people moving.

Wilson: Flow is one of the most favorite products due to the awesome UX. How do you decide what feature to build next?

Jesse: It’s a lot of things. We tend to mix what problems our customers are telling us they have with where we see opportunity in the landscape of project management software out there. We also have to take stock of older features that might need a re-thinking, re-engineering or re-design. This hasn’t always been the case, but this approach has been fairly consistent since I joined last year. We like to balance our intuition with what customers are asking for and also use what hard data we have to make roadmap decisions.

Wilson: As the VP of Product, how do you foster a good relationship with the engineering team?

Jesse: Easy, they’re my friends. I work with them constantly. I historically have a design leadership background, but I’ve always found that if you don’t have a friendship with your engineers- you’re pretty much fucked. I typically enjoy and prefer the company of engineers even though I am a designer historically. Designers are great too, there just shouldn’t be too many of us in a room at once.

Wilson: How important would you say it is for a Product manager to listen to their customer’s feedback?

Jesse: Listening is important. Understanding the core of what their problems are is even more important. Understanding what kind of customers you are targeting is very important as well. I don’t try to simply do whatever I’m told by our customers, I try to solve their problems.

Wilson: When it comes to user research, what are your go-to tools?

Jesse: We’ll often use fullstory, which allows us to redact people’s sensitive data while watching how they use the interface. We also talk to our customers on a regular basis, and ask them questions about what their needs are. We use Kissmetrics to monitor usage. We’ll often reach out to people using intercom. We also have a feedback forum that aggregates user’s requests.

Looking for an all in one feedback tool that integrates with Intercom where you can embed simple one-click/Net Promoter Score surveys and trigger on page website feedback widgets? Check out YesInsights!

Wilson: What do you think are the main differences between good and great product managers?


Great product managers are typically people who have themselves been in the trenches of making a product. Great product managers are just as at ease leading as they are managing. Great product managers are empathetic. I often refer to this writeup by Ben Horowitz as well on this topic:
Good product managers know the market, the product, the product line and the competition extremely well and operate from a strong basis of knowledge and confidence. A good product manager is the CEO of the product. A good product manager takes full responsibility and measures themselves in terms of the success of the product. The are responsible for right product/right time and all that entails. A good product manager knows the context going in (the company, our revenue funding, competition, etc.), and they take responsibility for devising and executing a winning plan (no excuses).

Bad product managers have lots of excuses. Not enough funding, the engineering manager is an idiot, Microsoft has 10 times as many engineers working on it, I’m overworked, I don’t get enough direction. Barksdale doesn’t make these kinds of excuses and neither should the CEO of a product.

Good product managers don’t get all of their time sucked up by the various organizations that must work together to deliver right product right time. They don’t take all the product team minutes, they don’t project manage the various functions, they are not gophers for engineering. They are not part of the product team; they manage the product team. Engineering teams don’t consider Good Product Managers a “marketing resource.” Good product managers are the marketing counterpart of the engineering manager. Good product managers crisply define the target, the “what” (as opposed to the how) and manage the delivery of the “what.” Bad product managers feel best about themselves when they figure out “how”. Good product managers communicate crisply to engineering in writing as well as verbally. Good product managers don’t give direction informally. Good product managers gather information informally.

Good product managers create leveragable collateral, FAQs, presentations, white papers. Bad product managers complain that they spend all day answering questions for the sales force and are swamped. Good product managers anticipate the serious product flaws and build real solutions. Bad product managers put out fires all day. Good product managers take written positions on important issues (competitive silver bullets, tough architectural choices, tough product decisions, markets to attack or yield). Bad product managers voice their opinion verbally and lament that the “powers that be” won’t let it happen. Once bad product managers fail, they point out that they predicted they would fail.

Good product managers focus the team on revenue and customers. Bad product managers focus team on how many features Microsoft is building. Good product managers define good products that can be executed with a strong effort. Bad product managers define good products that can’t be executed or let engineering build whatever they want (i.e. solve the hardest problem).
Good product managers think in terms of delivering superior value to the market place during inbound planning and achieving market share and revenue goals during outbound. Bad product managers get very confused about the differences amongst delivering value, matching competitive features, pricing, and ubiquity. Good product managers decompose problems. Bad product managers combine all problems into one.

Good product managers think about the story they want written by the press. Bad product managers think about covering every feature and being really technically accurate with the press. Good product managers ask the press questions. Bad product managers answer any press question. Good product managers assume press and analyst people are really smart. Bad product managers assume that press and analysts are dumb because they don’t understand the difference between “push” and “simulated push.”
Good product managers err on the side of clarity vs. explaining the obvious. Bad product managers never explain the obvious. Good product managers define their job and their success. Bad product managers constantly want to be told what to do.

Good product managers send their status reports in on time every week, because they are disciplined. Bad product managers forget to send in their status reports on time, because they don’t value discipline.

Wilson: What do you think is the single biggest mistakes new Product managers make?

Jesse: Ignoring technical debt. Simply thinking the job is making decisions about features, bugs and a date. Technical debt is the thing I’ve seen ignored the most over the years, and it always comes back to bite you in the ass. If you want to go fast in the long run, go slow. Don’t be sloppy. Make sure everyone on your team values craftsmanship.

Wilson: How important it is for a product team to get involved in improving trial to paid conversions and user retention?

Jesse: Critically important.

Wilson: What are your top product book recommendations?

Jesse: Don’t have any!

Wilson: Last question! What’s your main focus on Flow now and how can the community help? 😀

Jesse: I’ve got two more things I HAVE to do before I get to do what I WANT to do. In the short term I have to fix our onboarding, as well as implement project start and end dates. After that I get to focus on creating Focus. That’s all I’ll say about that ;). The community can help by telling us whether or not what we’re doing is working.

I hope everyone enjoyed this brief interview with Jesse, VP of Product at Flow. If you’re looking for a powerful way to take the guesswork out of knowing what your users want and gathering actionable feedback right away, sign up for our free trial at YesInsights! You’ll be delighted at the comments and feedback you receive from your users!


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Wilson is the co-founder of YesInsights. Wilson has been an entrepreneur and growth hacker/sales person for his entire life. Previously Wilson ran Head of Growth for Mobile Action, and Founder of InspireBeats (all in one lead generation solution). Follow him @wilsonpeng8 on Twitter

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