How did I get here?

How did I get here?

I was raised in a serial entrepenurial family, my parents had a party store – those in the Midwest know what those are, a catering company, meat market, and sandwich company. Plus, my dad was a charter fishing captain on Lake Huron for 25 years. Like many people, I grew up learning the value of looking your customer in the eyes and shacking their hand, the effect that a quick well-told story or joke can have on someone’s mood. Trust is built slowly over time and can be lost quickly in one action and the world isn’t out to get you, it’s indifferent.

My family would sit around the dinner table and my sister and I would watch my parents come up with a new product or service for their business. They would debate different ideas, decide on where they would take risks, where to invest time and resources, how to determine whether the plan was working or not, etc. Then, at work, usually when the bus dropped me off after school, my parents would get the team together and share the new idea. Oftentimes afterwards, I would hear employees around the shop talking about how they were impressed with what my parents had come up with and amazed at how they just kept coming up with new ways to improve the business and the customer experience. I would think to myself, “They just made that up last night while we were eating fried chicken!”

Like most people, I didn’t realize it at the time but this was laying the foundation for who I would end up being as an adult. After graduating from Michigan Tech with a Bachelor’s Degree in Computer Science, I knew I wanted to work for a small business, like what I grew up with, where I knew everyone on the team. I also wanted to work for an IT consulting company where I could work on a variety of projects for different clients, learning about different types of industries, technologies, company cultures, team structure, and leadership styles.

In 1999, applying for jobs online was possible, but it was definitely not the experience of today. I emailed my resume to one company. It seemed to check all the boxes on what I was looking for. Fortunately, it ended up being my first job out of college and the perfect bridge from small family owned retail business to small family owned technology company. I quickly learned that much of the way my parents operated their businesses was evident in how this technology company ran. Ideas were debated professionally amongst a group. We built trust with our customers over time by being laser focused on what they needed and then delivering on commitments. When things didn’t go according to plan, people spoke up. It wasn’t all roses. I learned the hard way not over commit. I also learned a lot about the politics of large (and small) companies.

In early 2000, the dot-com bubble had started to collapse and by late 2001 I learned that contract workers were one of the first variable cost resources that companies cut when financials get tight. I found another opportunity and remember calling my current boss and owner of the company to tell them. They were disappointed that I was leaving. They were investing in me, why wouldn’t I continue to invest in them? I was surprised by the reaction. I had expected them to be relieved to have one less paycheck to write at the end of the month. When I told my parents how it had played out, they weren’t surprised. My dad said, “To you that was a job. Maybe a bit more since it’s your first real job after college, but a job none the less. To the owner of the company, it’s a personal extension of their identity. It represents much more than a group of people or jobs.” Even though I had grown up and identified with our family businesses myself, I still hadn’t seen that one coming. It took a couple years before the owner of that company and I were on good speaking terms again.

My next move was again working with a consulting company. This time a bit bigger a couple hundred people. One of our largest clients was an automotive company. I learned a lot about how to combine agile thinking and quick results with the extensive business processes of large multi-national corporations. My manager, who turned out to be a long time co-worker and friend across numerous career moves, helped me move from an individual contributor role as a software engineer to a manager. As it turned out again, what I had learned up until that point helped me take these next steps. Being a good communicator, patient, empathetic, and certain that even when I had a good idea that someone on the team probably had a better one all helped. Eventually, I was offered the opportunity to take on a new project for a new client outside of the automotive space. I jumped at the chance to build a 15-person team from scratch in a new remote development office to deliver on a million dollar project. Over the next 9 months, we invented our own processes to streamline development and had a great time doing it. When we finally delivered the end product to our customer they exclaimed, “Thank you. This is more than we had asked for and better than we could have hoped for. We’d like to never work with you again.” Needless to say, that last part was not what I was expecting. As it turns out, the processes we had developed did not include much in the way of keeping our customer up-to-date on progress and our decision making. I learned that clients and business leaders do not want their projects to play out like mystery novels.

After about six years in consulting, I realized that I had only been involved in the middle of software development projects. I wanted to see the full process, from ideation and inception to production maintainence and enhancements. So, I took a role directly with a company that I had been working with as a client. Shortly after I joined, the owner sold the company to an international investment firm. The person that was put in charge made it clear from the outset that the firm was more focused on selling the company for a profit in a few years than what the company actually did. As it turns out, I learned a lot here. With the new owners focused on only the short term profits to improve the balance sheet, the medium term viability of the company began to suffer. Their lack of ability to effectively lead people created conditions where the best people on the team left. Someone, on their way out, asked me why I was still there. I had realized that this may have been the first jerk I’d worked for, but it likely wouldn’t be the last. So I wanted to learn from the experience. Practice influencing that kind of person. I continued to explain to the owner that the team they had was highly skilled and could deliver some industry redefining product and that we needed to treat them better or they would continue to leave. Eventually, I began to realize that it was my turn to either put up or shut up. If these rockstar builders of technology are looking for a place to do great work, I could connect them with some of the bold leaders I had met along my way. So, I left to start my own consulting business with two colleagues, one who eventually became my spouse.

I quickly learned that being in a family of business owners is as similar to running your own business as being in a family with a racecar driver is to being behind the wheel of an F1 car during a race. That is to say, not at all similar. What we had going for us was our personal experience leading a wide variety of different types of software development projects in a diverse set of cultures and environments. We also had developed a strong network of rockstar builders (software developers, product managers, program managers, scientists, designers, etc) as well as fearless leaders and visionaries looking to make bold bets on disruptive ideas. So, we connected those two groups. Things started off quickly and we soon learned the peridoxical nature of free cash flow. We had to manage our growth to ensure we didn’t over commit to either our customers or employees. We were very fortunate in that we had all good customers, which from my previous experience was not always the case. The company grew consistently year-over-year, but both my wife and I were starting to realize that helping others deliver on bold visions was more fulfilling than running our own company. In 2010, we were presented with an option to roll our company’s team into one of our customers and we took it.

In summer 2012, I was approached by a well known global eCommerce company that was looking to build the first corporate office in the Great Lakes region. As I started to meet more of the people on the team, I realized the level of engineering excellence, business acumen, the mechanisms to scale were far beyond what I had experienced. I also saw it as an amazing opportunity to give back to the community of people that had helped me along my career path. Bringing a Big Tech company to the region would have broad positive impact. In preparation for the interview process, I reflected on the 40-some different teams, cultures, and industries I had been fortunate to work in and how that had shaped my views of technology, system, teams, leading, culture, and people. There was no “right answer” or “right way”, just more and less effective approaches. Business and tech require Systems Thinking and giant doses of curiosity and humbleness. The interviews went well and over the next eleven years, I learned more than in the previous twenty. I was able to help grow the office from three to six hundred while recruiting some of the most talented technologists both locally and globally. Our group of passionate skilled rockstars have solved seemingly impossible challenges while creating a culture of fearlessness, inclusivity, excellence, trust, and customer obsession.