Melissa von Holstein of The Zebra: Product Managers Don’t Have To Have All The Answers

Reza Shirazi
Austin Voice of Product
8 min readSep 1, 2020

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Collaboration improves when you are humble and realize that you don't have all the answers, shared Melissa von Holstein, Senior Product Manager at The Zebra, for my interview series Austin Voice Of Product. Our interview has been edited for clarity.

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Austin VOP #87

What was your path to product management?

I did not know what I wanted to do in college, but I knew that I liked math and working with people. I studied industrial engineering, which was a good combination of both engineering and business. I went to the University of Oklahoma, and I thought I would end up in the oil and gas industry, but I took a chance and accepted a job in Austin at IBM as a software consultant. (I worked with Julie Varghese who you interviewed earlier this year.)

I was excited to move to Austin and travel for work, but I knew within the first couple of weeks that this was not the job for me. I stuck it out for a year because I committed to this job, but at the end of the year, my confidence was shaken. Coding did not come naturally to me and so I was questioning: do I even have a place in technology at all? I thought about going back into the oil and gas industry, but I found an unexpected opportunity at athenahealth, a healthcare IT company, for a product innovation role. The job description was very similar to my consulting role, but the main difference was that I did not have to code. The role utilized all my skills and did not call for requirements in areas where I was struggling. I am still so grateful that I got hired and ended up working there for about four years.

The product innovation role was a mix of business analyst, product manager and project manager. And over the course of the years I was there, it transformed into a true product management role. I was so excited because when I found that job I already knew how product development worked, understood agile methodologies and how to employ them. And I was working with a really smart, motivated group of people where all they wanted to do was make health care a little less broken.

That is how I got my start. I have realized that industrial engineering is a great foundation for product management because you are focused on optimizing the manufacturing process: solving problems and creating a better experience for the manufacturing environment. You are improving systems in the physical world and that translates well to solving problems with software as a product manager.

After many great years at athenahealth, I was ready for new challenges in a new industry, where I could also help grow the product management team. I am currently a Senior Product Manager at The Zebra, the nation’s leading insurance comparison site.

What advice do you give to aspiring product leaders?

What got me to where I am today is recognizing that true growth is found outside of my comfort zone. With every new product I start to work on or any new team that I join, whether at the same company or a new one, it feels like a completely new job. This was true over my time at athenahealth, as well as at The Zebra. I have switched teams multiple times and that has required me to be uncomfortable learning something new each time. I always say yes to a new product or new team, even though it can be daunting. By taking those challenging next steps and taking new opportunities as scary as they may be, you look back and you think — “Wow, I did it and learned so much from it.” With every new project, you take what you have learned and apply it to the next one in a different way. I have worked on B2B products, B2C products, and mobile apps. I had no idea what to expect before starting each project, but I was stretched and I learned.

Say yes to new challenges. Even if you are feeling uncomfortable about your work, know that you are not alone when thinking, “I don’t know how I am going to do this”.

One of the things that I love about product management is that every time you come to a problem, it is a new problem. You wonder — “How am I gonna figure this out?” You are applying some common things that you have learned in a new way. I still remember a comment my first boss made when we got a new initiative. I said: “How do you know what to do?” and she shared, “We don’t necessarily know what to do from the beginning, but you have to dig into the problem to fully understand it, brainstorm and experiment with different solutions, and then you’ll be surprised with how far you can go. And you have to remember you can’t do it by yourself in a silo either.”

That is a good reminder for product managers. You don’t have to have all the answers.

You have a whole team of people, not just your engineers and designers, but your users and your stakeholders to bounce ideas off of, too. The expectation of having to know all the answers isn’t realistic, especially when you join a new industry, company, or team. By having the humility to realize and accept that you won’t know it all and focusing on learning from different perspectives, you will gain the knowledge you need while building trust with your team.

What have you read/watched/listened to that has inspired you lately?

One book that came to mind is The Introvert Entrepreneur by Beth Buelow. It has always been close to my heart because I am an introvert. I am friendly and outgoing, but I have never been the loudest person in the room. So I used to wonder, “Where is my career going to go, and am I equipped to be in a leadership role?” I am not an extrovert like the majority of leaders you see, but this book made me realize that there are so many introverted leaders, CEOs and founders. More importantly, I don’t have to compromise my own personality or exaggerate it to make it ‘seem’ like I am a leader. I can still be an introvert and lead. That is so important to know because you may be shy or introverted, but it does not make you any less qualified to be in a leadership role.

What is exciting about the product you are working on now?

I am excited about everything happening with The Zebra right now. Most people can agree that shopping for insurance is not a fun task, and auto insurance, in general, is just such a peculiar industry. The value of auto insurance is to give people protection, to give them safety, in case something bad happens. If you get into an accident, you have financial protection with insurance. However, most people would agree it is one of the least trusted industries. You see ads everywhere, you get bombarded with phone calls, direct mail, and emails getting sold on which company is the best, and that can be overwhelming.

Our product vision at The Zebra is to be your trusted insurance adviser.

The Zebra is here to be your partner for all your insurance needs. We are dedicated to educating consumers on what coverage is best for you and your unique situation, and we want to take on as much of the work we can when you need to make changes or re-shop in the future, all while providing a superior consumer experience. Whether you are comparing your personalized quotes online or you are talking to our licensed independent agents on the phone, we want you to leave our experience with the confidence that we helped you as best we could.

I find that super exciting because no one else in this space has been able to achieve that. It is an industry that is still very driven by monetization, but our vision is to truly help people.

My focus right now is to build products for our independent agents. This is the first time we have had a dedicated product development team for this department, and that is the exciting and challenging part for me currently. I find it very fulfilling to start from scratch, getting developers on board and having the team fall in love with what the agents do, the challenges that they have, and what possibilities are out there. The agency tools were built when the company first started and now we are investing in scaling and optimizing them. They are helping customers all day, every day, and we finally get the chance to listen to the agents and solve their problems. Being able to help make their jobs easier, which in turn will provide a better consumer experience, is definitely the most exciting part for me right now.

What is your biggest product challenge currently?

Building a new team to evaluate, rebuild, and scale legacy systems is a challenge. Our business has grown tremendously, but the agency tools have not scaled with the business. We need to build a new foundation before being able to make large, innovative changes. The biggest challenge is to reverse-engineer their previous systems, understand how those tie in to current and future business processes, then make sure we build it in an integrated and scalable way.

How might we build a stronger product community in Austin?

This is even more important during a global pandemic — mentorship. As my dad would always say: it’s not what you know, it’s who you know. That is so true, especially in a place like Austin where people are just so willing to listen and help.

If there was a way to match mentees with mentors that have the skill set they’re looking to level up on, that could pay dividends in the end. Networking will always be an important part of life, so we need to take advantage of the Austin community and connecting with people one-on-one. Learning from other product manager’s experiences (the good and the bad) is so valuable because we’re always learning with each new opportunity we have. Sometimes you have to figure it out as you go, but I would love to know who I could go to for advice.

We would all benefit from case studies from peers and leaders to see what they have learned and how you can apply it to your context. Learning about roadmapping, or building a completely new product, working with different stakeholders, handling difficult conversations, and the list could go on and on. There is so much nuance to what we do as product managers that is not written down anywhere and there are no prescribed answers.

Last question, what is your favorite product?

I love this question because I have an immediate answer, and anyone that has ever worked with me will not be surprised. It is an ongoing joke with my colleagues that I am the Lucidchart Queen at The Zebra. While we learn about and build upon these legacy systems, LucidCharts makes it easy to create visualizations of the architecture, business processes, and user journeys. I am such a visual learner, and Lucidchart has been a huge lifesaver for me, especially while working from home since it is a simple way to communicate complex ideas.

Thank you, Melissa!

Austin VOP is an interview series with current and future product leaders to build a stronger product community in Austin. Please like, share and tweet this article if you enjoyed it.

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I am passionate about building products and building community. PM by day and community builder at Austin Voice of Product: https://austinvop.com.