Trailblazing Women in Product Management: Heather Wiederstein, VP of Solutions Development (Head of Product) at Learning Ally

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For our next installment of the Trailblazing Women in Product Management series, I interviewed Heather Wiederstein, VP of Solutions Development (Head of Product) at Learning Ally. View the full list of this blog interview series to learn the stories of more women product leaders here.

How did you get into product management?

I joke with my team that none of us went to school to be Product Managers. We have fallen into it from some other role. I fell into it being a subject matter expert. I started my career as a classroom teacher and have been working in educational publishing since I left the classroom. Because I was a teacher, I was able to be that voice of our customer. Because I design and develop software for teachers, I think about myself standing in front of the classroom. As a Product Manager, understanding the personas and pain points of the end user, the teacher, was very intrinsic to me. And it was easy for me to build trust and have conversations with customers (other teachers). When there was an opportunity to step into a product management role, I took that opportunity and jumped into the deep end, figuring it out through trial and error.

Any missteps along the way?

My gravest misstep was not speaking up (because I didn’t believe I had the “right” to speak up) when I knew a launch was going to go badly. I was more junior and came into the role as the product was about to be launched. I hadn’t been there for any of the requirements gathering or development. There was a lot of momentum built and I didn’t feel like I had the leverage to say that we shouldn’t launch when the CTO wanted to. Instead, I tried to create a mitigation path and I wish that I had had the nerve to not launch. It created so much havoc for the customers in my backlog for 15 months. If I could offer one thing as a lesson learned, I’d tell PMs to speak up when your gut tells you to. Be as data-driven as possible, and succinctly raise your argument.

What do you like most about product management?

I like solving problems. It comes from my education framework. Right now, I’m working on a product for struggling readers. I like solving the problems for educators who are trying to reach those students. I don’t approach it from a feature perspective. I approach it from the problem. How can I solve that problem? What is the ideal outcome or behavior?

What do you like least about product management?

What I like least is the very natural tension between a Sales team’s desire to close the deal and what that means for the product roadmap. When the Sales team makes a promise for something that we are not planning on doing, I have to be the one who goes back to either the sales rep or the customer and figure it out. Again, I come from the problem space. I ask what is the problem that you’re trying to solve because there might be a different way that we can do that. I don’t like being the bad cop after the fact. I’d rather be brought into the conversation as a partner with the customer and sales. Maybe what they’re asking for is right and the roadmap should pivot, but until we understand what they’re trying to solve, we don’t know. It’s much harder to go in after a promise has been made. I’ve learned the importance of having multiple versions of a roadmap for various purposes/audiences. I always have one that I can share with sales or a customer.

When you’re hiring, what are you looking for?

I definitely look for experience in how to build a product, but that’s not the only thing I’m looking for. I think there is a secret sauce. There is a set of soft skills that lend themselves very well to be a Product Manager that are not articulated on a resume. I’m looking for critical thinkers, problem solvers, communicators, and creatives who then also have a technical background in terms of software or our business’s area of expertise.

What advice do you have for women who want to get into product management?

Apply for the job. I think that when women don’t feel like they check all the boxes, they won’t apply. Apply for the job. You’ll learn it as you go. Be sure to communicate how your other skills and achievements lend themselves to product management. Take the risk. Make the hard sell. Don’t worry about the boxes you don’t technically check—show how capable you are of checking them.

Any guiding motto or principle that you use?

Content is King! I don’t think this is unique to education, but because I live in the EdTech space, this really rings true with our customers. We could build the sexiest technology and most beautiful app, but if we don’t have a real solution to a real problem inside that app, we are just making a widget. The content of what we are building is so important and where I ask my team to live all the time.

Download the Trailblazing Women in Product Management E-Book


View the full list of this blog interview series to learn the stories of more women product leaders here.

About the Author

Mira Wooten
Director of Solutions

Mira (she introduces herself as half of a Mira-cle) is your 280 Group concierge. She helps clients navigate our training and consulting solutions, and also oversees our contingent-search recruiting practice. As a certified life and systems coach, Mira is great at listening – not just to our customers, but to our entire 280 Group team. She has a wicked sense of humor and a song for every occasion. Click on our chat button to say “Hi” to her!

280 Group is the world’s leading Product Management training and consulting firm. We help companies and individuals do GREAT Product Management and Product Marketing using our Optimal Product Process™.

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