Matt Baxter of Bestow On The 5 Habits That Can Accelerate Product Development Cycles

An Interview With Hannah Clark, Editor of The Product Manager


Silent reading times for meetings. Plenty of product teams complain about meetings taking up precious time, but I’ve found that only poorly run meetings slow down product development. A very effective way to ensure everyone is on the same page before meetings start is by providing written information and spending the first few minutes of the meeting doing a silent read. This allows everyone to process the information on time, but it is still fresh and ready for discussion.

All new products start with an idea and then continue through the stages of development. What are the 5 habits that can accelerate product development cycles? In this interview series, we are talking to product managers, founders, and thought leaders who can share stories and insights from their experiences about how to accelerate product development cycles. As part of this series, we had the distinct pleasure of interviewing Matt Baxter.

Matt Baxter has nearly two decades of experience in digital product development across multiple industries. With a foundation in web development and UX design, he became a product manager to help companies focus on maximizing customer and business impact through their digital products. Over the last several years, he has provided product leadership within tech startups and is now a Director of Product Management for Bestow.

Thank you so much for joining us in this interview series! Before diving in, our readers would love to learn more about you. Can you tell us a story about what brought you to this specific career path?

I have always been interested in technology and figuring out how things work. My mom used to buy old electronics from thrift stores for me to take apart! Entering college, I knew I wanted to work in technology and pursue an engineering degree. During that time, I came across a book called Designing Interactions which digs into the stories of influential designers in technology. This book was my first introduction to the concept of product design. Until this moment, I did not realize there were jobs not just to make technology work but to design it for people. After graduating, I moved into software development and user experience design. From there, I realized I could combine my knowledge and make a move into product management with a strong understanding of how software products were built.

Do you have any mentors or experiences that have particularly influenced your approach to product development and user experience?

One of my first creative directors often said, “share early and share often.” He emphasized the importance of regularly getting feedback and iterating. This early lesson shaped my approach to product development, teaching me the value of early critical feedback on any project. More importantly, this developed my ability to receive all feedback without taking it personally.

Learning how to be vulnerable and unafraid to share in-progress work takes practice. I quickly learned how to do this through a method this design team had called “Collab Lab,” where each team member would present their in-progress work that week and receive critical feedback.

It has been said that our mistakes can sometimes be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

This isn’t specific to product management but a relatable early-career mistake. As I left for my first vacation as an employee, I tried to be a bit clever with my out-of-office responder. While I tried to set up a rule to respond to only people within my company, somehow, I set up an inbox processing rule instead, which promptly replied to every email in my inbox with my message.

This resulted in everyone at my company receiving dozens of emails from me notifying them that I was out of the office. I was mortified! The lesson is that it is possible to be too clever, and sometimes just doing the simplest solution is the best.

What do you feel has been your ‘career-defining’ moment? We’d love to hear the lead-up, what happened, and the impact it had on your life.
My first product management job was with a startup focused on saving people money on prescriptions. Honestly, I wasn’t super excited about the industry — I assumed the pharmaceutical industry would be slow-moving and dull. But as I settled into the role, I realized the beauty of a startup is that no matter the industry’s typical way of moving, a startup, by nature, embraces the opportunity for change.

With that change of mind, I saw an incredible possibility to have a meaningful impact on people by helping them save money on critical medications. This has changed the way I view opportunities — there can be tremendous potential to impact the lives of people in industries that might otherwise seem slow from the outside. Since then, I’ve decided a critical factor in my career decisions will focus on potential impact over how flashy the opportunity looks from the outside.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Early in my career, I struggled with determining a focus — I had always enjoyed both the technical development of software and the user experience design. When I realized product management was a viable way to combine both, I spent several months applying to many jobs where I was promptly rejected for not having enough experience.

I was disheartened and considered returning to a UX job, but I realized this was a critical juncture. If I gave up too soon, I knew I’d miss the opportunity to have a fulfilling career. Thankfully, I didn’t give up and eventually landed a product manager role, ultimately leading me to Bestow.

How do you stay on top of market trends and developments in the product management space?

Amazingly, many product management resources and online communities are available now — when I first heard about product management as a concept, I had no idea where to start. Most of my product management news comes through Twitter, email newsletters, and podcasts.

If I had to recommend one resource, it would be Lenny’s Newsletter; it’s a weekly newsletter with excellent product management content, a great podcast, and an active Slack community. Whether someone is new to product management or several years into their career, it is an incredibly valuable resource.

What role does cross-functional collaboration play in accelerating product development cycles, and how do you foster effective collaboration across different teams and departments?

Cross-functional collaboration is one of the most high-leverage ways to accelerate product development; almost nothing else has the same potential. At Bestow, we ensure continuous cross-functional partnership in two ways. First, product teams are composed of members from engineering, product, and design to ensure tight alignment and collaboration. Second, we ensure that work is not siloed during the product development process. While product managers may lead the discovery phase of development, they bring in engineering, design, and other stakeholders to participate in the problem definition. There is also no point at which work is “thrown over the wall” to be another team’s problem now; we work closely together from start to finish.

Helping everyone understand how their work plays into the final output of the product and viewing themselves as owners of the outcome is critical to effective collaboration. The worst thing that can happen is for teams or departments to look out for their interests or view their job as just delivering their slice of the work. Everyone owns the outcome; seeing others as partners to reach that goal is vital to collaborating well.

Thank you for all of that. Here is the main question of our interview. Based on your experience, what are your “The 5 Habits That Can Accelerate Product Development Cycles”?

1. Align on the problem you’re solving before you start.
So many issues will be avoided by an early focus on what, exactly, you are looking to do. This alignment can only happen when the cross-functional team explicitly aligns with the highest priority problem to solve. To be clear, this doesn’t mean you must achieve group consensus at the beginning! Teams should be ready to “disagree and commit” to test out ideas for solutions, but they must align on the problem. Product development will be blocked when contributors debate the solution if they disagree on whether the problem is worth solving.

2. Make clear, well-structured, written communication a team value.
I’m a firm believer in the idea that “writing is thinking.” The product team at Bestow encourages a strong writing culture; any time a product manager comes up with an idea — whether it’s a new feature for our product or a change in process for our team — they write up a proposal for it. This proposal will outline the problem or opportunity, why it’s crucial to take action now, and what value we’ll see from it. Then, the rest of the team can jump into the document, leave comments, and start a conversation about it. This process helps us all level up our thinking and strengthens our proposals.

It’s easy to get excited about an idea, but when you dig into the details, you discover new problems you didn’t consider. You will reveal problematic logic and unconvincing arguments by putting your ideas into well-structured writing. The written word allows everyone to see the same thing and develop a stronger shared understanding. Plus, you can share it with others who weren’t in the room, and they’ll have the same communication.

3. Ruthlessly prioritize every initiative.
Everything your team works on must be ruthlessly prioritized to understand what business and customer impact it will have. Many things will sound like good ideas or a good use of time, but the impact assessment tells a different story.

4. Prioritize learning quickly over getting it right the first time.
Product development is about creating something new and innovative, which often means doing something nobody has done before. Before launching a product, it’s easy to get stuck in analysis paralysis, worrying about whether you’ve picked the proper set of features or if you will be successful. Many things can only be learned by putting a product in the wild and seeing how your customers react. Of course, you should minimize significant risks and use critical thinking, but the longer you take to get something in the market, the more you increase your risk of building the wrong thing.

5. Silent reading times for meetings. Plenty of product teams complain about meetings taking up precious time, but I’ve found that only poorly run meetings slow down product development. A very effective way to ensure everyone is on the same page before meetings start is by providing written information and spending the first few minutes of the meeting doing a silent read. This allows everyone to process the information on time, but it is still fresh and ready for discussion.

What are some of the common pitfalls that you see product teams fall into when trying to accelerate their development cycles, and how can these be avoided?

Our instinct is always to jump to solutions when a problem is raised, but it’s the biggest pitfall I’ve seen. When a team skips a thorough discovery process, they’ll often be convinced it’ll be simple to pull together a solution quickly. Inevitably, the team will find themselves swirling on a decision about the solution.

Besides just prioritizing discovery, there are two ways that product teams can avoid this. The first is by ensuring cross-functional discovery — problem definition meetings should also include designers, engineers, and stakeholders. I’ve seen teams view discovery as something done only by product managers and stakeholders, but it is so much better when all disciplines are involved. The second way is by ensuring cross-functional alignment on the problem being solved. I encourage my teams to make sure they have explicit alignment on the problem being solved with others before starting the solution phase.

Can you share an example of a time when you had to make a tough tradeoff between speed and quality during a product development cycle, and what was the outcome of that decision?

I find that framing “speed versus quality” is not always the right way to build a product because it sounds like one option is delivering something of poor quality. With that approach, the people that will feel the pain the most are your customers. And putting the burden on your customers is never something an excellent product team should do.

A better way to frame the tradeoff is by choosing between speed and scope. In most cases, you can deliver a product to customers by reducing the scope to the critical components that address their essential needs without compromising quality. At Bestow, we carefully balance speed and scope with every Enterprise partner we launch. Even the simplest-looking insurance product can quickly grow in scope when you get a closer look, so we balance timeliness and thoroughness to launch platform solutions on time that deliver meaningful value to our Enterprise partners.

How important is a data-driven approach to product development, and can you share a story where data significantly influenced your decision-making process?

A data-driven approach is critical; without it, priorities will be driven purely by whoever has the strongest opinion or by anecdotal stories that aren’t representative of reality. At Bestow, we use data to help us find opportunities for improvement in our application process. By instrumenting each section of the process, we can identify where customers run into user experience challenges. As we identify those opportunities, we run incremental experiments in the process. We then rigorously use data to tell us whether it had a positive, neutral, or negative impact to inform whether it should be a permanent change.

At a previous startup I worked at, we provided customers with a dashboard to see how much they’ve saved on their prescriptions, get reminders about prescription refills, and claim their rewards based on usage of the service. Once we dug into the data, it became clear that most customers never revisited the dashboard after signing up. After analyzing the data and reconciling it with the type of product we were visiting, we realized that our expectations of how customers would use the dashboard didn’t match the reality of how customers were using our product. We decided to sunset the dashboard because we realized it wasn’t worth the maintenance cost for our small team. We moved all functionality to email and text notifications resulting in much higher engagement from customers being able to view their savings and claim rewards.

Can you share an instance where user feedback led to a significant pivot in your product development strategy?

One way Bestow’s strategy has changed over time is in how we view customers’ ability to self-service the life insurance process. Bestow began as a direct-to-consumer company to enable individuals to quickly and easily acquire life insurance coverage independently with as little assistance from an agent as possible. As we’ve developed our Enterprise offering, a significant piece of it enables their agent distribution arm. As a direct-to-consumer company, we optimized for customers to self-serve all parts of the process. However, as we worked closely with life insurance agents, we learned how critical their involvement and guidance in the process is, which they can only do with the proper access to information and tooling. While many customers can acquire life insurance on their own, there is still a lot that needs the assistance of an agent to help them make the right financial decisions. Through this, we’ve learned that there is a balance to strike between giving individuals self-service capabilities while empowering agents to help their customers at specific points in the process.

We are very blessed that very prominent leaders read this column. Is there a person in the world or in the US with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them :-)

I’d enjoy the opportunity to sit down with Tobi Lütke, the founder and CEO of Shopify. I’m amazed at what he’s built from the ground up, and I admire the principles he built Shopify on. I’ve listened to several podcast interviews with him and am always impressed by the level of deep thinking he applies to everything. I’d love to hear stories about the things he’s learned along the way about product development.

Thank you so much for this. This was very inspirational, and we wish you only continued success!

About the Interviewer: Hannah Clark is the Editor of The Product Manager. With a background in the tech and marketing spaces, Hannah has spent the past eight years coordinating, producing, and curating meaningful content for diverse audiences. Great products are at the heart of her life and career, and it’s her mission to support current and future product leaders in an ever-evolving industry. Read our latest insights, how-to guides, and tool reviews at



Hannah Clark, Editor of The Product Manager
Authority Magazine

Hannah Clark is the Editor of The Product Manager. With a background in tech and marketing, Hannah has spent the past eight years producing meaningful content