My Product Journey

Leadership Awards

My personal and professional journey as a Product Manager.

Growing up in a start up: Lessons from a childhood home that was also an office.

As a Director and PM for ManuLife, dad was always busy. I was born in Arizona, and my Canadian mother stayed home to raise my 2 younger brothers and I. Like my grandparents, my father decided to move us east, and bootstrapped what became the longest running (and most successful) MGU. It was wildly successful for over 22 years, and now that it was sold, I begin to look back at lessons that made its longevity so rare.

  • Knowing your customer, and identifying a niche.
    My dad helped write the book on self-funded insurance and medical stop-loss ( the niche).
  • Risk management – consistent and an industry best – by hiring nurses for key roles. They were the customers, the SMEs, and turns out they were very, very good at their new jobs.
    • Goal of not getting too big, nor greedy. This is partly why the average MGU lasts 2 years, and in general, why many companies fail. I was a teenager during the Financial Crisis.
      • I wrote my application to the U.S. Naval Academy and other colleges in his office, listening to him and his COO navigate the GFC, hoard cash, and keep clients and employees.
      • I saw a different perspective. Focusing on his business, not knowing if I would have a roof over my head day-to-day, and experiencing it all knowing that even one layoff – for my family’s benefit- meant an employee wouldn’t have healthcare and kids wouldn’t go to college.
      • No layoffs. In fact, the focus on quality, relationships, having industry experts in-house, and an extremely talented but rare COO (who wasn’t known at the time), meant the business continued to grow, I kept a roof over my head, and most fascinatingly was watching competitors get bailed-out at the end of it all.
  • Stick to your core competencies and develop a moat around your Product and business.
  • When you exit and sell, it’s tough to let go. Importantly, live your values. Stay away from stupidity, be a smart leader, have a great COO/CFO (again, a needle in a haystack here), and don’t give up power so you can stop those who say “F*** the employees” during the exit.

Remember your family helped build it too. I’m lucky to have these experiences that frankly you only witness if you’re a successful Entrepreneur. I’m lucky to have had mentors who were CEOs of major players, but one common thread: They all came from nothing and worked hard from the bottom up.

Living in China and Japan: Following passion for language, culture, and being a young Leader faced with immeasurable challenges (and why the award I got is bittersweet)

Applying to the Naval Academy requires a serious, 2 year commitment. I knew there was a chance I wouldn’t get a waiver for asthma, but I tried anyways. At the time, I was Senior Class President and served as Junior Class President prior. When they didn’t grant the waiver, I wasn’t surprised, but it meant I was a month behind regular College admissions. Thankfully, my sponsor and Lacrosse coach went to a school that happened to have a 4 year Chinese language program (rare at the time). He was able to get me a shot at admission, and thankfully they accepted me. I hadn’t visited the campus before I committed.

I still keep my medical waiver rejection letter from USNA on the wall behind my desk as a reminder that it’s worth chasing your dreams and following through. You never know if you don’t try.

My Freshman year was rough because, while everyone had fun, I had Chinese class and language lab at 8am – 11am every day. I was very good, having done homesteads across China during High School, and my years of Music Theory – and playing the Trombone and Drums – gave me a good sense of tonal language (important in Mandarin).

My Sophomore year was the most challenging year of my life. I had Chinese courses, Econ, and all the regular stuff. I still wanted to be a leader and grow those skills, and with being a Naval Officer (I say temporarily – still hopeful) off the table, I needed a community. I joined an academic focused, law fraternity, founded down the road at Cornell. The Chapter was the longest running in the nation and the house huge with giant pillars. I was accepted and pledged that year, taking Chinese, and working very hard to complete the program.

That Fall, I was initiated into the brotherhood. The board of trustees (which I now sit on) was headed by a retired Green Beret who became a good mentor. I was surrounded by people of good character and a well known Fraternity.

We also had to elect our new E Board (house executives). Somehow, I managed the courage to accept a fellow pledge-class brother’s nomination. I knew I could lead from prior experience, but never had a Sophomore taken on such responsibility nor been elected President.

3 weeks after becoming a member, I gave a speech in front of all the Juniors and Seniors. I must have made an impression, because that night, in shock, I was elected the youngest President in our Fraternity’s history. Unfortunately, a week after, someone with hidden mental health issues (who was straight A student and honor society member), tragically took his life. I was thrust into a situation that was mine to manage, not just as an Administrator of essentially a franchise and business (books to balance, leases, etc.) but also a campus leader. I was thrust into the spotlight and had to find a way to turn the situation into something positive, and importantly, lead the school through the grieving process. I was also focused on my job. I had to bury emotions, be confident, and put together plans to get the school and the brotherhoods on campus, back on track.

It started with initiating a mental health program with the Faculty and School administration. I brought in a program to train faculty to identify people in distress, and processes to help them in a safe way. I also started training for the student body to help prevent this, and also spread our learnings to other schools. For the brothers, I focused on happiness. I was one of few who decided to live in the house (many couldn’t anymore), setting an example that we must move forward the best we can. I held a formal (usually once a year) at least every month, bringing brothers and their girlfriends, and inviting the Dean and school president, faculty too. We would dress up and have fun, and I’d make sure we won “best decorated house” for Christmas.

I focused on charity. We did food drives, bought presents for adopted families, and while we were recognized for it, I could see making a positive impact whenever we could – and celebrating it with empathy – giving back to the community, helped us all move on.

Lastly, the bittersweet award. I was awarded “Outstanding President” out of all the National fraternity candidates. I have this on my LinkedIn, and appreciate the words said in the Press, but honestly, as I was quoted saying, it belonged to everyone. I think I learned a lot about leadership, humility, and how to lead through a crisis. Importantly, I turned around the Fraternity system’s relationship with the school (and another award, in the form of a rec letter from the Faculty’s Standards Committee). The campus was a better place at the end of it, and everyone was working together to build a better community. Unfortunately for me, it took a toll on my health, and after my term as President ended, I refused re-election to ensure continuity of leadership development, and was then diagnosed with a medical condition. I had to fight another battle, this one personal, and that is how I ended up where I started my career in sales. At the time I felt very down, but that is when I met my now-wife, and with her support and that of the Deans and faculty, I recovered and graduated on time (and a lucky summer Environmental Studies class in China for credit).

Field Sales: Forcing myself to do the one thing I didn’t want to do, but knew I needed.

I’m a great sales person, it’s in my blood. I never wanted to do it. But I knew I needed the skills and experience. I took the first job I got. UPS is an amazing business and they have a world-class training program. I had a company car, and was by far the youngest sales rep on the team. Funnily enough, beyond the rec letters I had, it was the fact I wore a watch and the way I spoke that made the impression I was responsible enough to handle the clients I worked with. Supply chain and logistics are no joke, and I had to do intense training to learn a lot – quickly. I had clients shipping arms to the military. I had to get ACTs and SATs to students desk across the USA, on the right day, the right time (to the minute), and the right student’s desk. One minute late, and they had to reschedule their college exams. In that case, I had a few natural disasters to work through, but thankfully my international studies made me a quick learner, and I was able to leverage UPS’ vast portfolio of Products (and planes, trains, boats and trucks) to get things re-arranged.

I spent 2 years driving around, visiting clients of every industry and type, cross-selling with Enterprise solution reps from every business unit – including insurance. Field sales is hard. Sales is hard. Supply chain is hard and unpredictable. If a “weather satellite” going cross-country isn’t routed properly, so it stays below a certain sea-level limit, millions would be lost. I was both AE and AM, so whatever I sold I managed, and that ended up teaching me a lot about the sales job. I also got to work with so many companies that it fed my entrepreneurial genes of curiosity. I could learn different businesses of all kinds, inside and out, how they operated, meeting with CEOs and small businesses everyday. No industry was off my schedule, except for one – Software.

Leap of Faith: Setting a goal of being a Product Manager. Choosing an unlikely path.

How in the hell am I going to get into Product as a new BDR? I knew it would have to start by building my personal brand, and, I needed to hit the ground running, taking the 6am train, working my butt off, and ensuring I was a top 1 or 2 rep. Results, and staying curious.

I was intrigued by my childhood hobby of Computers and programming. I was looking for a purpose, and knew Tech was it. I also knew, from my father’s journey, I wanted to be a Product Manager. I couldn’t afford grad school. I was working at UPS and investing whatever we had wisely, saving the rest. How could I go from there, to a Product Management career, with no background or degree? Turned out I needed to take another leap of faith and I took the first tech sales job that would hire me.

I was demoting myself to BDR, learning a new industry, but staying curious. My goal was to be a Product Manager. My best friend is Head of Product at Google, and I loved what he did. We worked Drama tech together in Middle and High School, were both proud geeks. I was jealous and knew it was my calling from watching my father grow his business in the same field he was a PM.

A company called Litmus that shared my values and was ready to scale up. Like my youth, I knew being exposed to that process and growth would teach me a lot. I didn’t think I could make it to Product but, like with the Naval Academy, I knew I had to at least try.

I don’t think anybody knew when I started that my goal was to be a PM. Only when I wrote a proposal for a product, slacking it to every director and VP, CEO, etc, I knew, that folks got wind of it. But even then, I wasn’t sure. I did know, from my dad, that knowing the customer, and many sales skills, would set me apart from other PMs and eventually, perhaps, I could start my own business someday.

I remember sending the CTO/Founder an email my first quarter there, simply asking why we were using C# for a certain backend system. He gave a great answer, and that was the last time we spoke. It was things like that, small interactions and learnings, and taking big bets, that would get me to Product. But I still had to be a top performer, even if I was taking CS50 classes on the train rides to work.

More to come… including resume, etc.

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