wHAT’S yOUR problem

Break into product management, and build your career through mentorship.

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About The Book

I’ll be honest with you—I was an idiot out of college. I was twenty-two when I graduated. I thought I knew everything about everything and thought I knew exactly how to forge my career. I had a serious wake up call when quit my job with no prospects lined up and found myself wondering what to do with my life. 

I knew I didn’t want to be a developer anymore but had no idea what to do next. I kept falling back on the same questions. What else can I do with my technical background? How do I find mentorship? OKR’s, design thinking, jobs to be done, stakeholder management – what do all these “product” buzzwords even mean? And why should I even use them? I found these words so daunting in fact that I wouldn’t even apply to a job if they were on the job description! It wasn’t until I realized how to change my mindset and found product management where I truly found my calling. In this book I will teach you how to use your technical background to get into product management.

I’ll show you the process I used for breaking out of the nitty gritty of software development to discovering customer problems. Then breaking down those problems to the root pain point. I’ll provide the framework I’ve established to forging meaningful and lasting connections with your customers and stakeholders. I will show you how to do this while finding the best mentors in the business and growing yourself. Let my unconventional way to find mentorship in the most unusual of places guide your next moves to build your career.

I will share my unconventional method to find mentorship in the most unusual of places.

What’s inside


Build faster connections with anyone

Connect faster and easier with your stakeholders


Land your dream job

Get past imposter syndrome and stand out among all the other product managers and land the perfect job


Use design thinking principles to find a problem

Empathize with your customers, find their root problems and build solutions to solve them


Truly serve your customer

Be the voice for your customer when they can’t be in the room


Find mentorship in the most interesting of places

Use my unconventional tactic to find mentorship


Lead your product team

Utilizing all these other tactics you’ll be ready to lead your team with confidence.


Just because you can do something doesn’t mean you should.

You can write code and fix bugs, but in your heart what you really want to be doing is solving the bigger, more impactful problems, or setting the vision or the strategy for the products you’re working on. You’ve spent years in the weeds of getting the exact technical specifications to work, while all the time you’ve been thinking about if this is actually something that needs to be made or if it should be made in this way.

I was where you are: building applications, taking orders, and focusing on the minutiae. It took some deep soul-searching and stepping back from a company I helped found, but eventually I found my way. Now I lead teams of developers, managing the production of multiple applications every year for a massive healthcare organization.

In this book I’ll explain how I went from working at Starbucks to earning over $100K. I’ll give you the process I’ve established for the entire concept-to-launch of a product. I’ll provide the repeatable method I’ve developed for how to find and solve problems down to the root of them. And I’ll show you how I product manage my career in order to reach higher and constantly improve. Through this book, I’ll teach you how you, too, can leverage your technical background in development to become a product manager, getting out of the weeds, handling the big picture, and helping solve the bigger problems.

My Development Journey

I’ll be honest with you—I was an idiot out of college. I was twenty-two when I graduated. I thought I knew everything about everything and thought I knew exactly how to forge my career. While in college I started a company with my roommate, Scott Tian,

to work on application development for local businesses. Scott and I were both studying computer science at the time and wanted to put what we were learning into practice, beyond the boring projects we were being assigned in school.

We developed an app for the University of Delaware campus, went to some pitch competitions, and made some connections with people wanting app development. Through those connections, we got hooked up with another college startup company, now called Carvertise, that had just gotten some funding. Carvertise is a company that pays people to drive their cars while displaying advertisements.

Carvertise came to us with a problem. They were collecting so much GPS data and ad impressions but had no way of sharing it with their customers to demonstrate the value of their service. When we sat down with Carvertise’s CEO, Mac, we asked him a ton of questions to discover exactly what problem he was trying to solve. We drew up a contract and got to work. Shortly after that contract was completed, Mac wanted Scott and me to come on full-time. When we graduated college, our development company was acquired by Carvertise, and we were now the third and fourth members of Delaware’s fastest growing startup.

We were moving up, successful in our chosen field, and yet I hated it.

I began to realize I couldn’t stand the nitty-gritty of app development. I loved our initial meetings, where Mac was a customer and I was gathering requirements. I loved figuring out how we could solve his problems. After I joined Carvertise, I turned into a straight-up developer. I went from a 50/50 balance of strategizing new business development and coding to then being a code monkey with only 10% strategy. While I was in the weeds, I couldn’t quite understand what I didn’t like about this job. I thought it

was that I now had a boss, or that Mac and I clashed heads so much on strategy. In actuality, I loved those difficult conversations. Mac and I both wanted what was best for the company, but we had such different ideas of how to get there from a technical perspective.

What I realized after three years of working with Carvertise was that I just didn’t like doing the development work. I was sitting in silence with my best friend, Scott, in front of a computer all day. We only talked when we were pair programming, or when one of us needed help with something. Spending hours debugging, with only the slightest reward of solving a pesky little error in the functionality, just wasn’t for me. I was surrounded by people at a quickly growing startup, but I felt so incredibly alone. It wasn’t the company, it was that I was doing the wrong thing. I loved having conversations with customers, hearing problems that we could solve for them, crafting roadmaps, or pitching which direction we should head in to our CEO. I just didn’t want to have to code the solutions. I felt so isolated when I was fiddling with the code. I needed interaction. I needed reactions from people seeing a cool feature we created. I needed connection, and I knew I would never get that as a programmer.

After that realization, I left Carvertise. I had spent three years with them but didn’t have anything else lined up. I knew that I didn’t want to code but had no idea what to do next. I wanted to start my own company again. I wanted to get out of Delaware, and I just needed change. I interviewed at a few places for software development jobs and other technical positions, but ultimately decided to work at Starbucks while I figured out what I truly wanted to do with my life. 

Pre-Order to find out what happens next!



So many people starting out in their career seem to have the same questions. How do I stand out? Why can’t I seem to say no to my stakeholders? How do I find mentorship, especially in this remote environment? In this book I will give you my strategies for standing out in the sea of job applications and making imposter syndrome your ally. I’ll show you to say no without burning any bridges and actually make your stakeholder relationships stronger. I’ll also show my unconventional tactic to finding mentorship. 

About the author.

Aaron Kesler

Aaron is an entrepreneur, certified product manager, and overall product enthusiast. Currently a Senior Product Manager at Blue Cross NC, he is working on new product development and developing product best practices across the Data and Analytics division of Blue Cross.

Aaron started his first company, STAK, in college which focused on development for small businesses. One of his clients was also a quickly growing startup called Carvertise. After working with Aaron on a few projects, Carvertise acquired STAK, making Aaron and his business partner the third and fourth members of the Carvertise team. While at Carvertise, Aaron wore many hats from Product Management to Lead Developer to Sales. Under Aaron’s technical leadership, Carvertise won Tech Startup of the Year 2015 for the state of Delaware.

After three years, Aaron moved down to Raleigh, NC on a whim. Working at Starbucks for a year, he met some absolutely amazing folks before he joined a slightly larger startup. He became the 30th member of TopQuadrant before going to Blue Cross NC in 2019. In his free time, Aaron created a SaaS solution for breweries called Perky Pints which focuses on driving business to taprooms. For fun he enjoys playing golf with his dad every Friday, traveling to foreign countries, and practicing ukulele.

Aaron Kesler

How to Manage Teams

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