From Coding Master to Master Manager: An Interview with Chip Cressman, Engineering Manager

Laura: Tell me about your path to Skilljar - what were you doing before and how did you end up here?Chip: I’ve been with Skilljar for almost 3 years. Prior to joining Skilljar, I spent much of my career building websites as a frontend engineer. When I decided to leave my previous job, I knew that I wanted to take my career in a more management-focused direction, but I didn’t have the experience to jump right into a managerial role. When I interviewed with Skilljar, I understood that I was joining an engineering team of five (including Skilljar CTO and co-founder, Jason Stewart), but I also saw the potential of the company and could envision it’s growth in the future.Laura: So you joined a company without managers to gain managerial experience?Chip: Yes, you could say that. It has always been a balance for me - working at a company that I love, doing work that I enjoy, while also keeping an eye on future opportunities and where I want my own career to go. Within a year and a half of my joining Skilljar, we had grown to the point where we needed to hire another frontend developer (in addition to me). Up until this point, Jason had created what I call “mini-management experiences” for me - project-based lead roles where I managed all of the work and the team.Laura: And then you hired Ian, our second frontend engineer?Chip: Exactly. And that was amazing and challenging and terrifying for me. All of the sudden, everything I said came with a “manager’s weight” and conversation became much more challenging because what I said, whether intentionally or not, was taken as direction or as expectation. I realized I was now speaking on behalf on Skilljar, not just myself.Laura: I imagine that was neither the first nor the last challenge you experience?Chip: Definitely not! The next hire presented an entirely different management challenge. With Ian, we shared a foundation of common knowledge and skills - so we already spoke the same language and I was familiar with his work. Our next hire, Edward, was a product designer, a role I had worked with in the past, but I’m not a designer. With Edward, I had to learn not only how to manage another person, but also manage a role that I did not work with on a daily basis.Laura: So now you know everything?Chip: I wish! The Skilljar team continued to grow so I now have nine engineers that report to me across three different teams! Every day is a new challenge and an opportunity to learn. Sometimes it’s exhausting, but overall, I’m so thankful for the opportunity before me. I have a great manager who is helping shape my career and I couldn’t be happier.Laura: Now that you’re officially on the management course, what are some of the biggest challenges you’ve faced?Chip: As an individual developer on an engineering team, you have pretty clear day-to-day to-dos and success metrics. Now, in my current role as a manager, my success is dependent on the success of my direct reports and that’s an entire shift in responsibility and mindset. I also have to keep in mind whether my team is happy and challenged on a day-to-day basis.Laura: Do you miss the coding?Chip: I do, yes. But I’m also fully confident in my team’s capabilities so I feel like I am able to step away and let them take the lead.Laura: Given your time and experience at Skilljar, what would you say to someone looking for a job in engineering here?Chip: My path is a great example of the investment Skilljar puts into each employee’s personal and professional growth. Not only have I learned an immense amount about development and engineering, I have also had the opportunity to shift to a management role in a way that was encouraged and aided by leadership. Becoming a manager can be a scary prospect, especially when you think of all of the people who now depend on you. Skilljar not only helped guide me on the managerial path, the company and my teammates have also consistently supported and advised me along the way.Laura: Any parting words?Chip: While my growth at Skilljar is far from over, one of the most impactful feelings I have experienced over my career here thus far is not just having a seat at the proverbial Skilljar table, it’s amazing to feel like I belong at the table at that my voice is both heard and valued.

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