Sean Smith has worked in the Boston startup community for the last six years in product. For the prior seven years Sean worked in consulting at PwC and Oliver Wyman in their tech and strategy groups. He grew up in Southeastern Mass, went to Wentworth in Boston for his undergrad and has been around the city since. Sean lives in Canton with his wife, two boys and two greyhound retired racers.
This article is about how a self-described “product guy” spent roughly six months quasi-leading a revenue function, having never done it before, and the lessons learned along the way.
Top Learnings:
- Just Say Yes!
- Get Started – Build Trust & Lead with Transparency
- Harness New Energy To Create Quick Wins
- Dig into the Numbers and Make Your Bets
- Resetting Strategy and Confronting Challenges Head On
One of my favorite parts of MGMT Boston is how Matt refers to folks working in the startup ecosystem as Operators. It’s not employees, it’s not the product leaders, it’s not founders, it is for operators, and at our core, we join startups to build and operate (and scale them, of course).
Well, through the course of operating, we’re all given opportunities to grow and do something different than our current role, and what the business needs of us. As some may attest, your role in a startup changes around every six months, so don’t get too comfortable.
Just Say Yes!
A new opportunity came to me this past summer, six months after getting promoted from Director of Product to VP and joining the management team at Denim. I was on a call with our CEO about coverage and how to help after parting ways with our revenue leader. I can’t remember the exact phrasing, but the request ended up being something along the lines of, “So if you could take over marketing and partnerships, and also keep an eye on the sales folks so that I can focus on the debt-facility work that would be huge.” At that moment, my answer was “totally let’s do it” and I thought to myself… How hard could it be?
Get Started – Build Trust & Lead with Transparency
My first priority was building trust with the team. To me, that was about being vulnerable, transparent and doing what I say I am going to do. I openly discussed my capabilities and intentions, understanding that my role as a leader was not just about directing but also about listening and supporting. Establishing regular one-on-one meetings was critical, providing a platform for open communication and understanding each team member’s career aspirations. I ensured that the spotlight shone on the team’s achievements, not mine, and focused on identifying the most pressing areas where I could make an immediate impact.
Managing and nurturing the team’s energy emerged as the next priority for the remainder of the first month. I took time to observe and understand what motivated them – be it small wins, collaborative efforts, or even just venting sessions. On the flip side, I also identified what drained their energy, including certain tasks and, at times, the influence of specific individuals. I tried to inject my own brand of energy into the team using humor (this might not work for everyone; your mileage may vary) and enthusiasm to keep spirits high. I also made sure to be responsive and engaging in our communications, especially on Slack, understanding the importance of these ‘small things’ in team dynamics.
Harness New Energy To Create Quick Wins
Having turned the energy in the right direction, I shifted my focus towards empowering the team. It was time to turn our good energy into tangible outcomes. I strived to be an enabler, making quick decisions and valuing the judgment of our star players. I worked on reinforcing a strong team dynamic, emphasizing the ‘win as a team, lose as a team’ ethos. This was most visible on pricing decisions for new deals, and on spending decisions for new initiatives. I was able to quickly absorb the key points and make a decision to keep the team moving fast and build comradery being in the trenches with the team everyday.
Dig into the Numbers and Make Your Bets
As the weeks turned into months, I started playing to my strengths. My experience in product management came in handy. I ran my own analysis to understand what was working and what wasn’t. I assessed our market focus, ensuring our activities aligned with our target customer segments. I made ROI decisions on new initiatives and contributed to team communication strategies (the big realization for me was in positioning and how we were really not pointing the direction where our target market was looking, instead attracting far larger prospects). This period was also about developing insights from my new perspective, carving out time for deep work, although not as much as I would have liked.
Especially as we were finding our new normal, I made a habit of over-communicating our learnings. I shared our progress and lessons with my team and peers, stressing that learning is a form of progress. This approach helped foster a culture of transparency and continuous improvement. In leading by example in my communication, I encouraged the team to share their insights and strategies, which contributed to a strong team dynamic.
Resetting Strategy and Confronting Challenges Head On
We took the reset opportunity to align on the strategic bets we wanted to make in our go-to-market motion. I was clear about the changes I wanted to make and involved the team in these decisions. By setting specific, measurable objectives and using structured templates to track these initiatives, we were able to keep a clear focus on our goals.
Looking back, I realize that not all my actions were part of a neat, pre-planned strategy. They were more responses to the challenges and opportunities that presented themselves. However, there were areas I wish I had approached differently. By resetting targets earlier we could have avoided a drag on morale by missing numbers with a smaller team size. Moving faster to put the right teammates in the right seats could have given us another boost.
Lastly, I realized the necessity of confronting challenging areas head-on, rather than avoiding them, as understanding them would have benefited both me and the business. There are still some parts of the GTM machine that I don’t feel very well versed in, and on my to-do list those areas kept getting pushed back and pushed back, and I know in my head I was avoiding it. I should just have bit the bullet.
At the end…
Overall, I had a ton of fun. I am glad I said yes and would absolutely do it again. Compared to Product, this was a new set of levers and tools to use, and the feedback loop was much faster (weeks and months in GTM instead of months and quarters in Product). It certainly helped that I have some incredibly talented, patient, and resilient colleagues for whom I will always appreciate and be forever grateful.
January numbers aren’t final yet but it is looking like our best month for pipeline ever (this is currently disputed in a Slack but I am optimistic my definition will win out 😀).
We have two co-founders at Denim; one is Shawn as well, so I have been happily known as pSean for Product Sean since I joined, well for a short while, the p was an r.
pSean