Career Change: Football Coach to Tech Startup

As the football season starts, I thought this would be a timely article describing some lessons in leadership from the last two decades of playing and coaching division 1 college football, what led to the career change to a tech startup, and adjusting to working from home.?

What does a college football coach actually do? Well, a college football coach does a wide range of activities including year-round recruiting, mentoring, training, game prep, and in-game adjustments. It is common for coaches to work 80+ hours seven days a week in the fall. The job is challenging and very rewarding, especially when you win, and get to see a kid grow into a man and graduate with a degree.?

Leadership Styles

Learning from some of the best coaches in college football has been a blessing, each with unique leadership styles. Here are just a few that stood out.?

Competitive: Coach Jim Harbaugh

As a student-athlete at the University of San Diego, Coach Harbaugh pushed us to a level we could never have imagined through an “Enthusiasm unknown to mankind” and a competitive spirit, unlike anyone I have ever met. Literally, every drill was a competition with a clear winner and loser. Coach Harbaugh even taught us how to dominate a handshake. Here is a throwback to Coach Harbaugh’s 2006 Dayton rivalry pregame speech.?

Yoda: Coach Dave Adolph

The best coach I have ever had, serving as my position coach and defensive coordinator for four years. My teammates now refer to him as “The football Yoda”, because of his Jedi mind trick tactics. For example, in the middle of dog days of training camp, he would ask, “Do you love football?” in his raspy voice. His meetings are interactive with a series of questions to engage in discussion and ensure players are paying attention, retaining the material, and able to think and react quickly on the game field. “It’s always easy in an air-conditioned classroom.” - Dave Adolph

“One day you will leave this game, make sure you have given it your very best, then you will feel very good about what you have accomplished” - Dave Adolph

Substitute the word game for anything: life, job, career, relationship, marriage.?

Teacher/Mentor: Coach Ed Lamb

An outstanding teacher and mentor to me throughout my first few years of coaching. He taught me the importance of a positive attitude and leading by example. Anything he demanded from the players, he was going to be side by side lifting and running with them.?

He taught the “Sandwich Rule” as a method of giving feedback or critique: For any piece of criticism, sandwich it in between two positives. The player hears the critique but comes away from the interaction feeling appreciated for the positive contributions and motivated to improve.?

Technician (Back-Engineer): Coach Dale Lindsey

The best at teaching the fundamentals of blocking and tackling. The drills are back-engineered so that the finish is taught first. For example, defensively, tackling is the first thing taught, specifically, the tackle's final phase. In fact, when the horn blows to start practice, it is mandatory that every coach starts practice with the same fit and finish drill called, “Giant Lift” to simulate rolling the hips to finish a block or tackle.??

If it were up to Coach Lindsey he would play the same defense every snap and out-execute his opponent with assignment, alignment, and technique. In fact, he actually did that in the greatest win in program history, where the University of San Diego with zero scholarships beat Cal Poly with 85 scholarship players in the first round of the 2016 FCS playoffs. Having been around the program for 15 years, this was an accomplishment I never thought was possible.?

In conclusion, the thing that these four leaders have in common is they have figured out a way to drive individuals and teams to accomplish things far greater than what could be imagined.?

Why Career Change?

This seems to be a common interview question. Why this career, why this industry, or why this company? For me, the top three priorities for me that led to my career change had to do with family, growth, and mentorship.

Family

Recently married last year, my priorities changed and it did not make sense for us to be moving around the country every four years with my wife having to restart her career. Working remote gives us the flexibility to move back to southern California where we first met.?

Growth?

There have been 32 NFL teams for the last 20 years and ~130 D1 FBS college football teams. So essentially no growth in football, while the tech sector seems to be growing exponentially, especially in a startup. The chance to get equity in a startup was appealing to me. It gives everyone in the organization an extra incentive to keep the top priority THE TEAM!?

Mentorship/Connection

So many times in business school I heard, that it's about “who you know”, making connections, and building relationships. It turns out that’s what led me to my current position at OpsLevel. For the last seven years, I watched my brother Colin Pentz and best friend Eric Bakhtiari grow in this little company called PagerDuty. The story was, that a couple of engineers from Amazon decided to start the company to provide a SaaS solution for incident response. Making life easier for the on-call engineer.?

These connections allowed me to get in touch with OpsLevel Co-founders, John Laban (the first employee at PagerDuty and former Amazon) and Kenneth Rose (former PagerDuty and Shopify engineer). In a small startup, leaders can wear many hats. For example, CEO, John Laban is involved in every step of the sales cycle from email prospecting to working with current customers and our engineering team to ensure we build the best product for our customers' needs. Leading by example.?

Onboarding from home

Challenges

The challenge for me onboarding remote has been understanding all the different tools and where to go to find information. Currently, I have 19 different apps or tools bookmarked on my google chrome browser.

• What do all these tools do?
• Where is the best place to go to find information?
• Who do I ping on Slack to find an answer?

This has actually helped me build empathy for our customers because the amount of tools software engineers use is multiplied, especially in modern microservice architectures.?

People - Surround yourself with talent

Steve Kerr is the best example I can think of who has surrounded himself with talent. As a player, he joins the Chicago Bulls with Michael Jordan and Scottie Pippen to win three NBA Championships. Jordan retires, then Kerr joins Tim Duncan and David Robinson to win two more titles with the San Antonio Spurs. As a coach at Golden State, Kerr builds the best roster in basketball including two MVPs in Stephen Curry and Kevin Durant, and is still winning titles!?

Great teammates are undoubtedly important to team success, but knowing whom to ask for a solution is equally important.?

It becomes extremely difficult to get to know your teammates behind a computer screen in a remote environment. For my immediate team, whom I meet with every day, sure I feel like we know each other pretty well.?

This past June at the company offsite in Miami 90% of the employees met each other for the first time in person (I know what you are thinking, a week in South Beach is a little aggressive for a first date). That week was extremely valuable for me to understand everyone’s role on the team. The thing that stood out most was seeing how focused each person is on building the best product for our customers. For example, I had no idea how much involvement our Customer Success team had with our current customers. They meet monthly to ensure the customer is getting the most value out of our product, asking for feedback on how to improve the experience.

Problem Solving

A significant portion of my job is problem-solving. Before we dive into the problem, you must understand the space. The traditional way of software development is writing one long piece of code in what is called a monolith. Over the last several years, starting with some of the bigger companies in the mid-2000s (Amazon, Netflix) began breaking down this monolith into smaller microservices in order to scale. Microservices allow developers to take ownership of a small piece of code and make changes frequently without stepping on anyone each other's toes. It is important that every service has an owner, description of what it does, and the tools needed to fix it. Typically this is tracked in a spreadsheet, but once teams start to spin up 50+ services, the spreadsheet becomes unmanageable. If someone needs to make a change to a service they did not build, how do they know how to fix it?

Step One: Identify the Problem

The first step is identifying companies struggling with "service ownership." Wasting time trying to find information about a service you did not build. This can be a result of ownership transitions such as reorgs, new hires, or incident response duties.

As a result, poor ownership can lead to unproductive teams and can affect the entire organization’s growth plans.?Because the DevOps category of “service ownership” is so new, often engineering leaders may not realize how much the problem is affecting the entire organization.?

Step Two: Connect with….(Jordan, Pippen, or even Rodman)

Once the problem is identified, my job is to connect the engineering leader with the best person on our team to explore a solution.

In the world of remote work, autonomy comes with accountability. A microservice catalog equips developers with a playbook to work autonomously: defining what a service does, who owns it, and providing the tools needed to make changes quickly. OpsLevel takes it a step further and measures the health of the services giving leaders a real-time holistic view. We call it “Service Maturity.”?

Conclusion

Great leaders have the ability to accomplish the unimaginable by setting ridiculously high goals, measuring performance through competition, teaching a step-by-step process through repetition, and celebrating success in a positive way.?

• As a leader, what is most important to you to drive a successful team? Feel free to leave a comment below.
• DM me on LinkedIn if you want to talk football or learn more about OpsLevel.
• Check out a demo here.