🤖 Matt Baxter: Bestow, Director of Product Management

Market-to-Revenue

Here’s what Andrew Miller said about Matt:

Matt Baxter. He's currently a Director of Product at Bestow, where I worked before Monograph, and he's just a great product leader. He was taking a brand new business unit to market when I was on my way out, and it was a huge project, and it was just so much fun to watch Matt do his work. I know he’d have tons of interesting details to share about the go-to-market challenges that he faced.
—Andrew Miller, Senior Growth Product Manager at Monograph → Listen

What are 3 ways that your team converts your market into revenue?

The three ways that I thought of really all revolve around making life insurance more accessible for people.

1) For individuals, life insurance is typically a multi-week long process that requires some doctor's visits. And so it's a really big barrier for people to actually go and acquire it. And so our platform cuts that down to just a couple of minutes and basically an instant decision. So that's one kind of with direct individuals.

2) Through empowering life insurance agents. So, they are really a key, critical part of the process for people to kind of navigate and figure out really what is going to work for them and what their needs are. And so we also use our platform to empower those agents, to do their job faster and easier.

3) Using our platform to enable other life insurance carriers to be able to sell term life more efficiently. Term-life insurance is typically a pretty low margin business, but it's something that people really want and need, and so we've been able to take our platform and make it available to life insurance carriers so that they can use it to sell life insurance faster in the same way.

What are 3 hard problems that you recently overcame?

1) Offering life insurance carriers our platform. That was basically what kind of my last year it looked like. It was taking the Bestow platform that we had built to sell directly to customers, and reorienting it, and evolving it, to be able to be the software as a service offering. And so there was just a lot of alignment and coordination across pretty much every team at bestow to take this one way that we knew of working with things, and the way that we thought of our platform, and kind of shifting it from a perspective of not just something that enables us to sell to our customers, but to be able to enable others to sell to their customers. And so definitely learned a lot of lessons just around giving people the right context, helping people understand why their pieces matter to this big, huge, whole of a project.

2) Scaling the Bestow product team. So when I joined Bestow, about two and a half years ago, we had a team of about four or five product managers. And now, our team is right around 20 now. And, that's just been a lot of learning around figuring out how to get all these products managers, and different product areas, to coordinate with each other, understanding the dependencies between them. How we can enable each other to ship faster and not get in each other's way as we're trying to get products out to market? Just learning how to coordinate with that group and to do it in a way that we actually enable each other instead of just have to work around each other has also been, I think, definitely a hard problem to solve, and something that we've been working on.

3) I'm sure a lot of people can relate to this, but I think especially the last two years, working from home. For me, I've got three young kids, from nine years old to three years old, and working from home, whether they had school lockdowns or when it's in the summer and they're at home, has definitely taught me a lot about just flexibility between work and life, where it's not as straightforward as just leaving, going to an office, and coming back a couple of hours later. But definitely learning to have more flexibility with that and give more grace to myself and to others.

What are 3 question that you love to ask and why?

1) What's just one thing that I can do, and feel like I've checked off, to start moving in that direction? So I was thinking about that from kind of a couple of different angles, for myself and others. One of the first things that came to mind is whenever I am getting started on somewhat of an ambiguous effort, or I don't really know kind of where to start with something, kind of the blank slate problem, is just identifying something that I can do to make just even a little bit of progress in the direction that I'm trying to go. Even if it maybe doesn't totally solve the problem that I'm trying to go for, it doesn't provide all the answers, I find just getting momentum on it is really helpful. So I always ask myself, “Okay, what's just one thing that I can do, and feel like I've checked off, to start moving in that direction?”

2) What is something that feels harder than it should be? A question I really like to ask my teams and coworkers as we're working through things, and looking for ways to improve things, is asking, “What is something that feels harder than it should be?” And so, I think it's a really good way to expose areas that maybe you've lived with in your product or your process, that some circumstances have changed, and you don't really have to live with that anymore, and you can find ways to improve it. Or, it just allows you to have some reflection and some areas that maybe have been difficult to figure out and untangle, and people have kind of avoided it, but it's an opportunity to really look at it and say, “Are we okay with it being this hard? Or is it hard for a reason that we can actually change and improve?”

3) What differentiates you or makes you more effective than other people in your role? One that I really like to ask others, just in terms of learning from them, and especially when I'm interviewing a product manager candidate is asking, “What differentiates you or makes you more effective than other people in your role?” So whether you're a product manager, if it's like other product managers, or engineer, and things like that, I think it's a really interesting question because I don't think a lot of people enjoy talking too much about the best parts about themselves, so it gives them an opportunity to reflect on that. But it also opens up, shows, what's important to them, and what they really like to focus on.

What are 3 mental models that you use to do your best work?

1) Get the problem as visual as possible and as quickly as possible. The first thing that I thought, and this is probably a whole bucket of mental models, but whenever I'm trying to work through something or figure out how things relate to each other is I try to get the problem as visual as possible and as quickly as possible. And so whether that's using my whiteboard and just writing it out or getting some sort of online whiteboard like Miro and just trying to map something out with sticky notes. I find that being able to visualize the problem space can help you to uncover patterns and figure out how things relate to each other differently than you might, even if you were writing about the problem, or if you were trying to explain it to somebody. And so, I know not everybody's a visual thinker, but it's almost always the first tool that I go to...