Deciding what to build next

Benjamin: I’d love to know how you got into product and product leadership.

Jen: My journey into product started because I fell in love with customers.

I started my degree thinking I was going to law school. But I realized that was going to be miserable. So I made a last-minute pivot during my last year at university to become a consultant, which is kind of “product management light.”

It was through that journey and working closely with customers that I realized my passion: spending time with people, understanding what they’re trying to do, how they’re trying to do it, their hopes and dreams, and then working very closely with a cross-functional team to figure out how we build, ideate, and deliver solutions at scale. That’s what got me started and passionate about product management.

When I was a kid, I didn’t play product manager with my friends. We weren’t building a startup in kindergarten or anything like that. This discipline has evolved alongside my career, and I’ve been very privileged to have had the opportunity to work at some phenomenal companies with some phenomenal people who have provided great training.

Creating a customer-centric culture

Benjamin: I want to dive into one of the things I feel a lot of people here probably struggle with: creating a customer-centric culture in an organization.

How have you approached that in your roles?

Jen: Walk the walk. Pretty much every conversation I start, I start with a customer. It’s an opportunity to demonstrate to the organization how I’m thinking and inspire them to do the same.

When people have an idea, I also ask them to contextualize it in conversations they’ve had with customers, or how they might test it with customers. And so, in many ways, it’s just infusing it as an expectation in the work we do.

Benjamin: Have you seen a particular process or tool help at all? Or is there anything you’ve done where you see teams really nail it?

Jen: I think there are lots of different ways to approach it. I realize that the way teams engage with customers is a function of the stage of the company, the idea, and the team’s culture.

With very early-stage ideas where we’re innovating ahead of where the market is, it’s harder to have a direct customer conversation and be like, “Well, I talked to Bob, and Bob said this, and so I’m gonna go build this for Bob.” It’s a little more abstract. You have to bring the customers along.

For more mature products or markets, there’s more opportunity to draw on the corpus in front of us.

People ask, “So what’s the essential skill for product management?” And I always say it’s communication. And they say, “Oh, so you have to be a really good presenter and writer?” Actually, the essential communication skill is listening.

If you can listen, hear problems, and find ways to bring those problems alive in an organization, people can’t help but innovate. I think engineers, in particular, love the opportunity to dig into a big meaty problem. If you can actually bring in a problem that enables them to bring their best to bear, it’s really exciting.

Benjamin: How do you drive that sense of ownership in a product team? You’re saying bring the problem and let the team figure it out on their own with that sense of empowerment and ownership. How have you created that culture?

Jen: For me, it’s been about looking to teams to define their goals, milestones, and expectations and then holding them accountable for the delivery.

I mean, the people I work with are all smarter than I am, so my job is really finding ways to encourage and inspire them to engage with customers, take ownership of the problem and define the outcomes. Then it involves holding them accountable for those outcomes.

As I’ve grown in my career and through different organizations, I’ve come to appreciate how important it is to provide strategic guardrails out of the gate. Because then teams can more easily figure out how and where they fit.

I’ve spoken to a lot of founders who don’t want to box people in—but it’s not about that. You need to help people understand what you’re trying to get and then provide some constraints or guardrails along the way that actually, I think, help facilitate innovation and focus. Otherwise, you might be wandering in the wilderness.

Benjamin: And it’s also about storytelling. It’s about how you play on people’s emotions and say, “It’s actually a real person who’s using our product.”

Jen: Well, I think it comes back to listening, because then you actually know who you’re listening to. And if it’s just numbers on a page, it’s very hard for people to internalize it and figure out how to make it their own.

Deciding what to build next

Benjamin: For me, one of the most difficult parts of a business, product team, and PM role is deciding what to build and what not to build.

How do you approach deciding what to build next?

Jen: I encourage teams to think about a roadmap as a combination of three buckets of things:

1. Trust. This is performance, scalability, reliability, and quality. Your license to provide them with new capabilities and continue to grow and expand with them is built on building, fostering, and extending that trust.

2. Insights. You can get insights from being out in the field talking to customers about what they want and like.

3. Innovation. This is where you can see problems and opportunities around the corner.

I encourage teams to think about these three buckets as a portfolio. At any point, one bucket might be bigger than another. But I think it’s really important for teams to give themselves license to invest across all three parts of the business. I think that’s what it takes to truly delight a customer.

And then there’s prioritization within the buckets, which, of course, is the next complicated bit.

Benjamin: How do you drive innovation and creative thinking, especially if you’re trying to create a new category?

Jen: Ask for it! A lot of organizations forget to ask for innovation. They get so focused on the next release or the next “thing” that they forget to ask people to bring their ideas.

The second is to expect it. Make sure there’s space in there that says one of your OKRs is to continue to innovate.

Finally, create a culture of learning. You need to create the flexibility to experiment and do so safely and to create opportunities to have those moments where things don’t go exactly as planned. Make sure these conversations take place and that people can be rewarded for that experimentation.

Influencing through insights

Benjamin: Being able to influence folks is a challenge that I hear over and over again.

Whether it’s a product manager, researcher, or designer who’s done some research, how do you get insights in front of the people who are setting strategy? What have you seen work?

Jen: There’s strength in numbers. It’s about bringing insights into the conversation and inviting people to contribute their questions. That’s a really good way to get people, at least on the team level, bought in. Everybody has questions, and you can help people suss out their questions. Giving them some space and airtime creates that initial buy-in.

It’s also about bringing those insights into a story by writing a blog post, doing a customer reel, or posting notes from a customer meeting. Sharing the insight is another way to get people interested and curious.

Also, show the victories. Say, “I’ve been out talking to customers. I’ve been driving insights. We’ve been asking questions, and we’ve used them to help us ideate. Here’s what we learned, and here’s the impact of what we delivered.”

Benjamin: As a founder and the person who has been running the product team for a while, I think it’s always nice when people say, “Hey, this is what I’m thinking. I don’t know about this approach, but I don’t really have any better ideas right now. Can we work together and riff on this?”

Often, when people engage more senior leaders, it’s very much like, “I’m gonna present my finished, polished thing to you.” But I don’t want to see the polished thing. I just want to see the working stuff. Let’s collaborate!

Jen: The fun part is getting in and being a part of it! Most people who are now in senior leadership positions started out doing that, and they never really want to give up.

When you invite people into the ideation, the conversations are also a great way to get buy-in.

Benjamin: In the last 18 months, there has been an economic impact on certain roles, including product management and research. Another question that comes up a lot from our customer base is, “How do I, or our function, do a better job of explaining the business value we bring?”

How do you marry user-centricity with the needs of the business and justify your existence? And not just your existence, but extra head counts so you can grow your team?

Jen: First of all, acknowledge that it’s been tough. We’re all having to learn and adapt.

In a competitive environment, insights become all the more important. It’s about pulling them through and tying them to business value.

It’s about helping people understand how the insights we’re seeing in the market are directly tied to what we build and sell. Or, on the flip side, it’s about saying, “We’re seeing a lot of attrition from a customer base under economic duress. Let me talk to some of those lost customers.” You want to help people understand what the other side might look like.

I think the greatest risk that businesses have right now is that, in the face of this economic shift, people decide to just turtle under, pulling in their heads and legs and hunkering down. But this is the time when turtles need to throw out their legs and head and go sprinting through the fields to find insights from customers! We’re all sprinting turtles in this moment!

Failing is the best way to figure out you need to do something differently

Benjamin: I think it’s becoming increasingly easier to build stuff. This makes figuring out what to build so much more important.

What have you seen work at Cloudflare and now at Plaid? What drives greater investment in customer insights besides the culture? And is there a specific initiative that you’ve rolled out that you’re quite proud of?

Jen: Failing is the best way to figure out you need to do something differently.

We live in this world where the friction to building and deploying things has never been lighter. At the same time, I think that sometimes makes it too easy for people to say, “That’s a great idea! We should do this!” And sometimes, you just have to let it run.

There’s no better lesson for an organization than coming up with a brilliant idea, talking to no one about it, shipping it, and having it go down like a lead balloon. So, it’s about encouraging people to see what we could do differently or what didn’t go as expected.

Benjamin: So when a project fails, how do you approach that with the team?

Jen: First of all, there’s no blame. We tried it. It didn’t go as we hoped. So, what did we learn? What’s the good news? What’s the bad news?

It’s about using that retro mentality of the lessons learned and what we would do differently as an opportunity to encourage people to just step back, learn, and then share those learnings.

Navigating the product management “moment”

Benjamin: I want to touch on the future of product management and how you see product management, design, and engineering evolving. Because I feel like it’s going through a bit of a moment.

For example, Airbnb has changed the definition of what a product manager is. It’s now more focused on storytelling and the product marketing approach.

Another thing we hear is that, historically, PMs did a lot of ideating, and now designers do a lot of that—and also that PMs used to talk to customers a lot more, but now we have researchers who do that.

So how do you see the PM role continuing to evolve? And do you have any advice for product managers on how to keep up with the times?

Jen: I sometimes worry that we’re creating a culture where it’s too easy to delegate the hard parts of product management. It’s really important for product managers to stay plugged-in with a greater sense of ownership over solving customer problems and being that tireless advocate for the customer.

Now, don’t get me wrong—product management is the ultimate art of managing through influence. It’s about being able to build relationships and trust, align groups of people across engineering, design, and marketing.

Don’t take your hands off the tiller. That’s my advice to people who are starting product management today. Don’t let go of—what I consider the funnest part of the job—conversations and relationships with customers. Continue to find ways to bring the customer and their problems alive. This helps the organization prioritize, understand, and deliver against those goals.

At the end of the day, product managers need to prioritize ruthlessly. I don’t know how they can continue to be effective if they delegate the things that actually help them build the instinct and insights that facilitate this.

Taking the next step in a product management career

Benjamin: I’m sure a lot of people are also wondering how they take the next step in their career—maybe into a leadership role.

I’d love to hear how you made that jump and some of the lessons you would pass on.

Jen: First and foremost, what is the pot of gold at the end of your rainbow? Because it’s different for everyone.

As I’ve grown in my career, I’ve realized that I really love customers and teams. Early on, I was like, do I want to continue to be that kind of prototypical, product management visionary art type? Or do I want to think about building and scaling teams? I pursued the latter path.

Now, caution! Building software is fun. Managing people is complicated. People are nonlinear, emotional, irrational, wonderful beings—but managing people isn’t the same. Compared to managing software, it’s a very different beast.

I see three or four steps in my career.

The first was going from individual PM to player coach, continuing with my day to day responsibilities while mentoring a couple of junior product managers.

The next was moving from player coach to pure player role, managing people who were managing product. That was the hardest step for me because I had to let go of the thing I really loved: actually doing the work. I had to figure out how to help people be successful at it and step out of the day to day decisions.

Watching somebody do something early in their career for the first time can be really hard. You have to coach people but then just let them do it.

Another challenge was realizing there was a very instantaneous feedback loop when I was building a product. I could build it and ship it; then people would use it… high five! In leadership and management, feedback becomes a little more ethereal. I had to really internalize the team’s success as the impact that I was able to help deliver.

Balancing what the user needs with what the business needs

Benjamin: How do you satisfy the needs of the user and the needs of the business when it comes to commercialization, pricing, and packaging? What are some balancing principles?

Jen: Think about how you are creating value and how you capture value. For me, creating value is what you’re doing for the user. Capturing value is what gives you the ability to charge for it.

I wish I had a magic wand for pricing and packaging! There are lots of different variable models. One of the things I’ve really appreciated with the evolution of some of the freemium or “plonk down your credit card and get going” kind of businesses is that people can get in and use some of the basic capabilities. It also gives organizations a chance to build a large corpus of users and learn from them. Having users who are new to your platform, constantly evolving, and finding easy entry points is critical.

Truly understanding the bare minimums your users need to get the capabilities and create the value, and then the hooks to move them up… I think that ends up being really powerful.

As they move toward commercialization, I also encourage teams not to just focus on how much revenue they make or how many users they sign up. It’s also about looking at adoption and active usage.

Product success can get very lost in the financials. I’ve seen that truly enduring companies don’t just think, how do I continue to drive a nice revenue business? More importantly, they think about how they make sure people are actually using the product and getting value from it.

Typically what ends up happening is, six, eight or 12 months before a big churn or attrition cliff, you’ll actually start to see adoption slow or tail off. To me, that’s the early warning signal that something needs to get sorted out in the product or the pricing and packaging.

Benjamin: Thank you so much for taking the time, Jen. It was incredible to get some insights from you!

Editor’s note: This article is a condensed overview of Jen Taylor and Benjamin Humphrey's fireside chat on the main stage at Insight Out 2024.