My Product Journey

My Personal and Professional Story

I found a company called Litmus that shared my values, was a fit to hit my goal of moving to Product, 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.

– My Professional “leap of faith“

From U.S.N.A. candidate, to Hobart College
My fate as a Leader, challenges, and why my award is bittersweet.

Applying to the Naval Academy required a serious, 2 year commitment. Early Application to show dedication, and focus. All while knowing there was a chance I wouldn’t get a waiver (for asthma) near the end. I followed the process, and tried, anyways.

I was Junior Class President when I applied, and was re-elected Senior Class President. I did my tests – including physical testing – with a close friend applying for Kings Point. At the end, and likely because of the Marine Infantry component of the Navy, I wasn’t granted a medical waiver. Although I hadn’t had asthma issues in many years, I wasn’t surprised, but it meant I was a month behind regular College admissions.

My sponsor, who sat on Maine’s Senate committee for Service Schools (including USNA) and was my Lacrosse coach, went to a school that happened to have a 4 year Chinese language program (rare at the time, and a focus of mine). He had just presented me a Senior Athletic Award for leadership and recommended me for admission at his alma mater, despite the admissions deadline passed. Thankfully Hobart College accepted me. I hadn’t visited the campus before I committed (only after accepting admission and an on-campus meeting).

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. To me, it’s a powerful reminder of many lessons in life, and serves me well.

My Freshman year. While everyone was having fun, I sat in Chinese class and language lab at 8 AM – Noon. Every Day.

I was very good at Chinese, having done home-stays across China & Japan during High School. 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.

My “President’s Year End” Letter to Faculty & School Administration

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 found a company called Litmus that shared my values, was a fit to hit my goal of moving to Product, 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 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.

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.

Key Lessons taken from watching my father’s Business

• Take risks. Don’t follow dogma. Identify a niche, know yourself and your customers.
  • Have a great COO/CFO. This was by chance, and why I’ll never follow “Dogma.”
  • Don’t focus on growth at any cost.
  • Focus on relationships, delegate responsibilities.
  • Consistency & Competency can’t be replicated easily. Be unconventional.
    • Hire SMEs (former nurses) for key roles. They knew the voice of the customer, the system, and it turned out, they were also very, very good at their new jobs.
  • 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. Live your values in these moments.
• The above, to me, made the difference – and are why many companies fail.
• A teenager during the Great Financial Crisis: Unique perspectives. Writing applications & homework in the office, down the road from school, I listened to executives navigate the recession, and how to keep clients and employees.
  • I saw a focus on fundamentals.
  • Not knowing if my family would have a roof over our heads, day-to-day, while knowing any layoff – even if for my benefit- meant someone wouldn’t have healthcare, and child wouldn’t go to college. I heard and lived this every day.
  • No layoffs. In fact, the focus on quality, relationships, having industry experts in-house, and an extremely talented COO/CFO (who wasn’t known at the time – and should write a book, in my opinion), meant the business survived – and grew. I had a roof over my head.
  • Perhaps most interesting for me was watching competitors get bailed-out.