Me (Jacob Burdis) with Nate Walkingshaw (CPO at Pluralsight)

Lessons Learned as a Product Manager at Pluralsight

The first time I ever heard of Pluralsight was at the Front Product Design Conference in the summer of 2015. Nate Walkingshaw’s presentation stood out the most, and not just because he was the only one wearing shorts and fresh kicks. I was blown away by his approach to product design and how understanding the psychology of how people learn plays a crucial role. After meeting with Nate Walkingshaw and Gilbert Lee and discovering Directed Discovery, I immediately knew that I had a lot to learn about product design and that Pluralsight was the best place to do it. After working only 6 months as a product manager for Utah’s Unicorn, I’ve learned more about how to design an amazing user-centered product than in all of my previous years of experience combined.


Having come from an organization that requires its employees to sign multiple-page documents describing the rules and policies for working there, I was surprised to learn that Pluralsight only has two rules for its employees:

  1. Be respectful, considerate, and kind, even when you disagree.
  2. Always act in Pluralsight’s best interest.

Really… that’s it. There is no vacation policy, no tracking of accrued sick time, no travel expense policy, nothing. Also, I learned that the entire sales organization wasn’t paid commissions. Just like everyone else, they were paid a competitive salary and expected to do their very best. We were completely entrusted to understand the two rules and apply them ourselves in our individual circumstances. Now, I know what you might be thinking (I thought the same thing too). What’s to stop someone from taking complete advantage this freedom? How can a company remain productive with such a lack of control?

I experienced a meaningful change in approach to my job when I understood that Nate, Gil, and Pluralsight completely trusted me. I felt intrinsically motivated to do my best. I found myself spending meaningful time on the problems I was trying to solve instead of worrying about more trivial things like how many hours I’d worked. I woke up excited to go to work, and often would have to be told to go home. Because I felt trusted, I wanted to be better and give my all. I was witnessing first hand the truth described by Johann Wolfgang von Goethe:

“When we treat a man as he is, we make him worse than he is; when we treat him as if he already were what he potentially could be, we make him what he should be.”

I realized that I should be extending the same amount of trust to those that I worked with if I wanted to see similar results. This was an important lesson for me as a product manager. My personality is such that I feel much more comfortable when I’m at the helm: when I’m in control. At first glance this may seem an admirable trait for a product manager, whose job it is to oversee a product from inception to execution. But I quickly learned that my job wasn’t to single-handedly control the process, but to facilitate it by giving up control to the team as a whole. I learned to trust users’ intuitions as we interviewed them daily. I learned to trust my UX designer as he captured the narrative in his designs. I learned to trust the developers as they brought the experience to life. As I fought the urge to exert my will and learned to trust the team to do their part, I saw that trust create an environment of autonomy which cultivated creativity. The rest was history.

If you want to learn more about this compelling concept, check out Daniel Pink’s book “Drive.” He cites a study by the Federal Reserve Bank that shows that productivity for cognitive tasks doesn’t increase through extrinsic rewards and incentives, but through creating an environment of trust, fairness, and autonomy.

Pluralsight Headquarters in Farmington, Utah


When I walked into the Farmington Office at Pluralsight for the first time I was stunned. I was used to pragmatic workspaces where entry-level employees got crammed into colorless cubicles while managers hid away in closed-door offices. No such nonsense here. There wasn’t a single office, not even for the CEO. All I saw were glass doors, glass walls, and inviting, open spaces. This was my first of many lessons about the importance of transparency, especially in an organization aiming to develop delightful products. The leadership team went to great lengths to keep us informed about all aspects of the company through regular all-employee “town-hall” meetings. Nate and Gil met with us consistently in team meetings and one-on-ones to give us deep insights about changes in vision and direction of the company.

Following this example, I learned to do everything in my power to be transparent about the vision and direction of the experiences my team was designing. In my previous product management experience, I felt that I was always on the defensive. The organization was constantly questioning decisions about the product, which resulted in a very unhealthy “us vs. them” mentality. At Pluralsight, I was taught to “go on the offensive” by disseminating the vital information which led to the decisions we were making. I conducted “Co-core” meetings twice a week to update and collaborate with other departments. Nate frequently had us present our progress and direction in all-employee meetings. I constantly sent out updates of our progress on slack, including daily accounts within the private product team channel. I recorded every user interview and posted a link to it on slack, and a few times pieced together shorter highlights from user interviews to accompany updates about our direction and decisions. Amazingly, the organization responded with overwhelming support. The questions we did receive were incredibly constructive, and usually spawned from others in the company watching our recorded user interviews. I learned that true transparency transforms culture, increases product clarity, and instills empathy in the rest of the organization.


My time at Pluralsight taught me the power an intimate team can have in the product design process. I won’t soon forget the feelings of camaraderie that Nate fostered among the larger product team. I was welcomed in with open arms. Instead of feeling the need to compete with and “prove myself” to my cohorts, I felt like I had access to dozens of mentors who were more than eager to show me the ropes. Nate also organized quarterly off sites where we focused on building the bonds between the team members and refining our craft. At one such off site, we spent several hours individually bearing our souls to the group, becoming vulnerable and gaining deep empathy for each member of the team. I spoke about things to that group that I’ve only spoken about with my closest circle. I still marvel at how Nate was able to put us all at ease with each other, especially since the gathering included several teams from several locations that I had never met before.

Pluralsight Product Team—Q3 Off Site in St. George

I learned how to weave the thread of teamwork into my daily work as a product manager. From day one, I was paired with an incredibly talented UX designer (Josh matson) in what Nate likes to call a “product couple.” Instead of me writing user stories and drawing wireframes on sticky notes and then giving them to the designer to “make them look pretty,” we designed the product experience together in tandem. Also, we were co-located with four amazing developers. Even though we reported to the CPO, and they reported to the CTO, we were a single product team. Every user interview we conducted included at least me, Josh (UX) and a developer. We participated in daily standups, weekly retrospectives, and were continually working together throughout the day to build an awesome product (the dev team likes to say we “kanbond”). We became good friends and learned to cooperate throughout the entire Directed Discovery process, which resulted in a smooth design and development experience because we all felt equally invested.

I’ve still got a lot to learn, but I will be chewing on these lessons for years to come. As I move on to my new entrepreneurial adventure, I feel more prepared than ever thanks to my time at Pluralsight; this job is definitely a hard one to leave. I hope that there are a few nuggets from my experience that can help any of you work to make your process and daily work more effective and enjoyable. More to come on the new adventure soon.

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