January 8, 2019

Career Path: Nicholas Leonard, Sr. Product Manager at Jobcase

What do the career path and day-in-the-life look for a Sr. Product Manager at Jobcase look like?

We connected with Nicholas Leonard to find out.

Also, Jobcase is hiring! Click here for all of the company's job openings.

Where did you grow up?  What did your parents do for work?  

I grew up in Muncie, IN, a once-booming factory town where high school basketball stars are deified. My mother is a NICU (neonatal intensive care unit) nurse. My father spent 20-years in an automotive factory, while also a helicopter test pilot for the Indiana National Guard. Just this month, he is retiring from military service after 41 years.

Where did you go to college?  What did you study and what were some of your initial jobs out of school?

I attended MIT here in Cambridge. My coursework was in Mechanical & Biological Engineering.

Nick Leonard and his family

Immediately after I received my undergraduate degree, I was a Design Engineer at Pratt & Whitney working on the propulsion system for the F-135 Joint Strike Fighter. I went on to join 2U, an EdTech leader, before working as an entrepreneur with educational nonprofits prior to joining Jobcase.

What has attributed to your success thus far and has helped propel you to the position you have now?

For me, it’s about seeking trust and understanding people: What motivates any given person? What’s the best way to communicate with that person? When do they need high five? When do they need to be left alone? Historically, my greatest personal failures are when I couldn’t establish a sense of trust with my teammates. Similarly the successes I have had are because a group of talented individuals - through trust - became a talented team.

Can you share the high-level responsibilities of your current position as Sr. Product Manager at Jobcase?

At Jobcase, it is my responsibility to understand our users challenges in their work-life and devise scalable technology solutions. The tricky part? There are dozens and dozens of ways we can help our members and limited resources we have to work on them. Ultimately it’s my responsibility to understand all of our members’ problems, gauge (or triage, as we say) the impact of solving the issue, devise a hypothesis that addresses the issue, and validate the hypothesis through rapid testing and ultimately build the full solution.

Any tips for someone considering a career in Product Management?

Discover your personal spike? Are you the connective tissue that breaks down organizational silos? Are you the brilliant empathizer that has an uncanny knack for understanding users? Are you the engineer’s best friends with your perfect articulation of features and needs? There are lots of things a Product Manager has to do. Understand your strengths and play to them. Where you are weak, you get to choose: Either improve them or build a team that mitigates your weaknesses.

Day in the Life

Coffee, tea, or nothing?


What time do you get into the office?

8:30 AM

What are three things that motivate you in your role?

Members - Jobcase’s platform is empowering tens of millions of jobseekers to take control of their work-life. Our membership is made of people from high school, my hometown, my current town - everywhere, and to be able to put faces and names to the people we support is incredibly motivating.

Teammates - Any journey is a lonely road if you go on it by yourself. I feel very grateful to have inspiring teammates.

Growth - At Jobcase, I’m given the freedom to experiment, access to great mentors, and the support to continue my education.

Every day is different, but can you outline what a typical day looks like for you?

  1. Coffee & Breakfast

  2. Prep for the Day

  3. Stand-up with Engineering, Design, Marketing, and Creative

  4. 15 minutes on engaging with members

  5. Ticketing for new projects

  6. Lunch & Coffee

  7. Rest of the day roughly spent these ways:

    1. Brainstorming new ideas across different teams (Sales, Customer Success, etc)

    2. Long-term planning (OKRs!)

    3. Research (Competitive Intelligence, User interviews, blogs)

    4. One-off issues.

What time do you head out of the office?

5:30 PM

Do you log back in at night or do you shut it down completely?  

Mostly, no. But when I do it’s because curious or so excited about an idea, I have to get it written down.

Any productivity hacks?

Decide early what you want to learn and what you want to rely on others for. We glorify ‘growth mindsets’, but at some point learning everything can become doing nothing. So, I recommend that when you know the things you learn, attack them early and to completion. For the things you aren’t going to learn, find someone you trust, and then trust them!

What are the 3 apps that you can’t live without?

  • Gmail

  • Slack

  • Fitbit

What professional accomplishment are you proudest of?

The Community & Product teams that I lead at Jobcase have grown 33% over the course of the past year, and we haven’t had a single person leave. I know perfection can’t last forever, but I’m proud that in 2018, everyone who was on my team or joined in midway through is still on it and excited about their work going into 2019.

Nicholas Leonard with Jobcase Softball Team

Who do you admire or call upon for professional advice?

I’m lucky that MIT facilitated a professional network of incredible entrepreneurs and business leaders for me. I feel incredibly blessed that when I need help, whether practical advice or just empathy, I have a network I can turn to. In fact, for most people don’t have a professional network that can provide the advice and support they need to advance their careers. It’s a daily reminder why our mission at Jobcase of empowering workers is so important.

Keith Cline is the Founder of VentureFizz.  Follow him on Twitter: @kcline6.

Images courtesy of Nicholas Leonard

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