12 Lessons in 12 Years

In honor of my professional life lasting as long as K-12 schooling, here is the most important lesson I learned in each year of work thus far.

2011: Software Engineer –> Designing a Data Warehouse is a technical and usability challenge. Ideal to have a single very wide table at lowest level of granularity (view or physical depending on database). Everyone mess up joins. Avoid duplicates. Pick descriptive and long column names.
2012: Solutions Engineer –> Cohort analyses are extremely helpful in understanding your customers (e.g new/loss/gain/churn over time). When in high-SKU domains (e.g eCommerce) product affinity analysis is also extremely valuable.
2013: Sr Solutions Engineer & first management role –> Engineering leadership must be done from the front. Communicate consistently and clearly explain priorities. If the team is staying up all night for a release, you are too. Hold yourself to the standards you hold the team to. Get coaching and learn. Listened to Manager-Tools Podcast and learned “When you tell a group of people something 7 times half will say they hear it once”
2014: Technology needs its own multi-year vision. Company, product and/or customer driven roadmap is not enough. Focusing on a core customer goal (High Availability for our largest client) led us to a multi-year delay in a more long-term important technology requirement for our business (native AWS).
2015: Director –> $500million acquisition! I led product demos + technology due diligence with prospective buyers. Before the deal closes there is a multi-year investments in relationships, clear narrative, consistent performance against prior commitments, demonstration of deep bench, and enthusiasm of all the principals.
2016: When something is working let it rip! I served as engineering + product leader for a segment of our business that hit $10m ARR in 18 months from launch. With just 3 engineers (and ~5 GTM folks!). We did this with extreme focus on customer needs, good early architecture decisions, and a very cohesive and strong team. Once growth hit this inflection point we should have invested dramatically more to define category and deepen moat against incumbents who had more distribution. We grew business to ~$25m ARR but it could have been $100m+.
2017: VP –> Recognition is the ultimate incentive. Money is a critical form of recognition (especially in a competitive market!) but in the end most people strive for status and recognition. Culture is defined by recogition and created with thoughtful org structure and operating cadence. Critical when balancing mission vs functional teams, creating career ladders, deciding compensation, and in creating org rituals.
2018: SVP –> The faster you need to execute the fewer objectives you must have. Narrow and prioritize. Then cut again. Dramatically increase expectations of quality and speed while dramatically decreasing number of projects and ‘decision makers’
2019: Sr PM at Slack –> Small companies have drama, big companies have politics. Understand the coalitions and competing goals. With many Type A people getting things done requires (1) willingness to heads down make decisions and ‘ask for forgiveness’ or (2) building coalitions for your cause. Know which strategy to employ in which circumstance.
2020: Brands matter. A brand is the expectations and emotions people associate with something. McDonald’s brand is so strong because it is consistent. Work to clearly communicate consistent expectations of your project/team to stakeholders (and follow through!)
2021: Proximo –> Stated vs Revealed preferences are very different. Social desirability bias is real. Potential users unintentionally lie during user interviews to (1) be nice to you and your ideas, and (2) showcase the best aspirations they have for themselves. Be careful to suss out true challenges and avoid solutioning too quickly.
2022: Proximo –> People were much more supportive of me shutting down Proximo than I expected. Customers, employees, investors all understood, respected the decision, and moved on to great things. Take chances - life is too short!