We Asked, They Told: 8 Product Leaders On What Keeps Them Up At Night

WalkMe Team
By WalkMe Team
Updated May 2, 2023

What current and future challenges give you pause?

My colleague Marie Lunney asked eight product leaders this question, and the answers they delivered were both insightful and varied.

Leadership, pricing, the global talent market, finding your competitive edge — the list goes on.

It’s clear that there’s no shortage of challenges, but the work product leaders are doing is integral to the success of their companies. Read on for a candid look into their perspectives.

Note: Responses have been lightly edited for clarity and length.

Kenneth Surdan, Chief Product Officer, Diligent

I think it’s that you don’t have the luxury of thinking about only one thing. I think about the customer a lot. I think about the competition a lot. I think about markets a lot. But in terms of the most important job we have, I still think it’s building the team.

Assembling and optimizing talent for your most important opportunities is the crux of what we do. Building teams with the right talent mix — the right balance between engineering and product management user experience — these things are hard to do.

You can have all the conceptual ideas in the world. You can have every great insight into the problem the customer has. But if you can’t deliver it, that all goes to waste. Following through all the way to execution and bringing it to market with quality is almost always about the team. Building that team is the foundation for me.

Adam Long, VP of Product, Automated Insights

Project managers naturally worry about everything. That’s kind of their job. We have to think about what can happen in the market that could totally invalidate what we’re working on, or that would change everything.

Sometimes we have to respond to a competitor entering the market, a new acquisition, a large partner going a different route, or breakthrough technology that refocuses the market in a different direction. So you have to always be prepared.

The other thing is that 90% of startups fail — not because of competition, not because of market forces, but from their own undoing. As you grow, all your communication pathways break when you double or triple in size. Or you make the wrong bets, spend too much time and money on them, and don’t learn enough in time about the market and where the value proposition really is and where the product should be.

So you’ve exhausted all your time and resources before you could fully understand these things, and you’re left questioning, “What bit of reality have we not tested, what major thing are we missing in the tests that we’re running, and which things have you spent too much time and money on that you’re not actually going to get revenue from?”

product manager

Etsy Yehuda, Director of Product Management – Web, WalkMe

There are five main challenges or questions that keep me up at night regarding new releases:

  • Will we launch it on time?
  • How will we roll it out?
  • What should be the next one?
  • How do we measure its impact?
  • How will the organization react?

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Scott Lowrie, VP, Strategic Business Development & Customer Success, Active Network

Formerly VP, Innovation, Product & Business Development, Active Network

Pardon the pun here: software is hard. What I mean by that is it’s becoming less and less difficult to actually develop software. There’re fantastic coders everywhere in the world these days.

Essentially, you don’t gain your competitive advantage on the technology itself anymore.

You really gain your competitive advantage on how you market it and bring it to market price. And then you add those little flavorful things that differentiate you from your competitors.

And so to me that’s really what keeps me up. It’s the idea of building a solution and saying, look, we’re the No. 1 or No. 2 player in the market. Nobody can catch us. We know, we’re good. That level of comfort doesn’t exist anymore in today’s world, because there’s someone in a garage somewhere, or somebody having coffee at a Starbucks who has an idea that could directly compete with you.

Steven Aldrich, Former CPO, GoDaddy

As we have more and more people entering the workforce over the next decade or so, half a billion people globally will eligible to work. How will we get those folks jobs? Well, it’s not going to be those of us in the tech community going out and hiring half a million people across the Fortune 100 each — it’s just not the way companies are built.

So we’re going to have to find a way to make entrepreneurship viable the path. Either these folks start their own business or they join small businesses that are already up and running.

Today they’re roughly 500 million small businesses around the world. So if each one hired one more person we could absorb that that demand. But that means that these businesses have to be successful. We know many of them fail and new ones get created.

And so I think the second thing that keeps me up at night again at a macro level is how do we ensure we have the right toolkit to create stability globally and allow people to pursue ideas? This is hugely important to the global economy — to keep vibrant the entrepreneurship routes that build what we have today.

product leaders

Cody Bender, Chief Product Officer, Campaign Monitor

The need to hire great people keeps me up at night. They’re hard to find because there needs to be a balance between the technical and the business side, but also a balance between cultural fit and competence.

I’ve worked with incredibly competent product managers, people who were better than I was at what we did — just phenomenal. But, culturally, they didn’t fit with the organization’s we were in, and therefore, it kind of stunted their ability to be effective.

Steven Kilpatrick, Director of Product Development, EAB

I always fear that competitors will get to the piece of the market, the next big feature, the next big move first.

Also, how do I communicate the overall vision to members so I can avoid a negative response? For example, I had a customer visit recently and I had to sit in a room with them while they told me that I made the wrong decision that impacted their users directly.

It was particularly difficult because I have a very close relationship with them and they wanted to back us into either re-implementing a piece of functionality or roll them back. The goal of this release was to allow a more streamlined workflow and flexibility in our platform, but it’s understandable that our members may not have realized that changes and releases may still benefit the majority of our users in a positive way.

Feedback is always a balancing act. I try not to take negative feedback personally but it can be a very hard thing to do. Still, I always know that the decisions we made were not done in a vacuum – it’s a team effort and we all have to stand behind our product and decisions.

Nate Walkingshaw, Chief Experience Officer, Pluralsight

Execution. How, as a leader, can I give the pictures in my head to every person on my team?

How do we go attack a problem and really make people feel that they’re a part of it? I strive for the Martha Stewart management style. She manages this billion-dollar company but she can go downstairs and bake you the best damn cookie you’ve ever eaten in your life.

I have to yo-yo between being an individual contributor and a leader. That’s why having a highlighted mission and vision is so key. It keeps you and your team members anchored. You can ask yourself if the work you’re doing right now aligns with the larger vision. If it doesn’t then you should probably work on something else.

Building a better future

Product leaders face a wide range of challenges as technology evolves and consumer demands shift. By sharing their take on the main factors that influence the future of technology, product leaders can expand their perspectives and hopefully improve their business.

Learning about the participants’ priorities and concerns has been enlightening — I hope for you too.

Thanks to everyone who participated.

WalkMe’s Digital Adoption Platform (DAP) transforms the user experience in today’s overwhelming digital world. Using artificial intelligence, engagement, guidance, and automation, WalkMe’s transparent overlay assists users to complete tasks easily within any enterprise software, mobile application or website. Discover how a DAP can revolutionize your business.

WalkMe Team
By WalkMe Team
WalkMe pioneered the Digital Adoption Platform (DAP) for organizations to utilize the full potential of their digital assets. Using artificial intelligence, machine learning and contextual guidance, WalkMe adds a dynamic user interface layer to raise the digital literacy of all users.