By: Jessica Dubin, Chief Product Officer, Remesh
My story begins with a personal decision after becoming a parent. I had been working within a large product organization as Senior Product Manager when I had my first child. At that point I realized that every hour I worked or spent time thinking about work was time away from my kid. The opportunity cost of working became much higher. I had already been feeling uninspired and distanced from my work, and becoming a parent amplified that feeling for me. I knew that I wanted to continue my career, but that I needed my work to be as fulfilling as possible.
I began to look for an opportunity where I could enjoy the people, be inspired by the technology, and fall back in love with product management. I knew that I had something to say when it came to Product, but I would only be effective if my voice resonated with the organization. I chose to move to a much smaller company with a nascent product team, keeping my title and salary the same. Even though this wasn’t a clear step forward for my career, my intention was to find work that aligned with my values and made the most of my strengths.
The Individual contributor product manager role has always been rewarding for me. I enjoy working closely with engineering and design to build something that makes customers happy and has clearly defined, measurable impact. My new team and I were completely in tune. We were able to identify new features that improved the user experience for our target audience and we delivered quickly.
Soon after I started this new role, I faced a big challenge when my boss left, and I was asked to lead the team. In fact, I was asked to take her exact role, which was VP of Product. I rejected this idea knowing that there was a long road of learning between Sr. PM and VP. But, I also knew that the team needed a leader, and so I suggested instead that I become a Director of Product. I deeply enjoyed mentoring Product Managers and helping them succeed, and I thought that with the Director title I could shirk the seemingly overwhelming task of creating product strategy.
I clearly remember calling a former manager who I respected to get his opinion on my readiness for the Director role. “Yes,” he said, “you are definitely ready, but you also need to have a product vision and direction. You can’t lead the team without it.” Of course he was entirely correct, leading a team without a clear strategy is like conducting an orchestra without sheet music. Since I didn’t have the experience to know how to best approach developing product strategy, I decided to pick something simple: focusing on removing platform friction. That clarity at least allowed us to create a decent roadmap that we could socialize while I, and my team, found our rhythm.
The Director role gave me the opportunity to create a culture of collaboration and risk taking within the product organization, and foster more collaboration between departments. I deeply enjoyed coaching the other product managers and dedicated an hour each month with each product manager in addition to our weekly one-on-ones to work on a professional development opportunity that we had jointly identified. Every 6 months, we used peer and stakeholder feedback collected through a survey to track progress and identify movement on the product manager’s strengths and weaknesses. One of my product managers shared that he received more feedback from me in one session than he had in his entire career up to that point.
I realized that creating a high functioning team was my highest point of leverage. With capable product managers, I had the time I needed to build relationships with others on the leadership team and better understand the business as a whole.
Though I had articulated clear boundaries for my Director role, (e.g. I wouldn’t join the executive team and I wouldn’t present to the board), those were quickly eroded as the company needed a strong product voice. I slipped into the executive function of a Vice President, without ever officially taking a title change. Becoming part of the executive team and presenting to the board gave me a new perspective on the details of the business. It was clear that our biggest revenue driver, services, was also our lowest ROI, and was draining our capital. In getting much closer to the business and evaluating my function’s place in achieving our company objectives, I began to develop a strong perspective on how we needed to change our business operations, and our product strategy. The product strategy became clear: make the platform accessible enough to be used without services.
In addition to providing a clear product vision for a fully self-use platform, I advocated for us to evolve our business model – away from selling low-retention services towards selling more self-use SaaS with higher margins and recurring revenue. It would require much more reliance on our platform, and the company was only just starting to trust the product team to deliver on that promise. There was resistance to this idea since we had a good amount of inertia with the existing leadership team, but that would soon be upended.
A big push for change came when we missed a mergers and acquisitions opportunity, and our finances started to look untenable. The CEO came to a small group, myself included, to let us know that the company would need to drastically cut costs, and asked for my support. Once again, I declined the initial offer. It was clear to me that unless we made a change to our business model, that we didn’t have a sustainable business. My position was clear: If we keep as much of our tech team as possible (40%+ of the total company) and retrench as a SaaS company, then I would stay. To my surprise, the answer was yes, but it also came with yet another role change as I was asked to be a founding member of this new iteration of our company.
I resisted publically changing my title to Chief Product Officer for a while because it felt presumptuous to me. At my prior company, a much larger organization, we would roll our eyes when someone went to a startup and got an inflated title. I didn’t want or need a title to know the value that I brought to the business. But eventually I acquiesced to a title change to create clarity on roles and ensure that the product function had a voice at the C-level.
The CPO role is still new to me. Now more than a year in, I still have much to learn. My scope is now the entire business. More than ensuring that Product’s voice is heard, it’s now important that all of the functions are harmonized. I care as much about Sales and Customer Success as I do about Design and Product. The C-suite is deeply involved in business strategy, managing costs and making strategic investments. It also sets the tone for the organization as a whole.
A friend recently asked me “what’s your takeaway on how you can best lead from the C-level”? I believe that it comes down to relationships. In the role that I left after having my first child, no one knew who I was outside of work. In one team building exercise where the product team drew representations of each other, my section was nearly blank with the exception of dollar signs – I was the Monetization and Billing PM, and a baby – I had recently come back from Parental leave. It wasn’t my team’s fault. I deliberately left my humanness at home in order to appear more professional. But what I have learned over these past few years is that building relationships is critical to professional success, and you need to be your full self in order to build deep, trusting relationships that can weather disagreement and business challenges.
To me, bringing your full self to work means getting to know people across the organization by setting up quick “coffee chats” and asking about their hobbies and interests. It means making time for socializing at the start of team meetings. In our Product and Design meetings, we always start with a Question of the Week such as “What fad have you recently been pulled into?” or “What’s the best under $100 purchase you’ve made in the past 5 years?”. And at the C-level, it means insisting on a definition of success, holding each other accountable and encouraging challenging conversations. Activities like these have not only helped me to find an authentic voice, but have also set the tone for a supportive and inquisitive work environment overall.
When I returned from parental leave after having my second child, one of the engineers reached out to say that she was glad I was back because the company felt different when I was gone. I was truly shocked to hear that since she and I didn’t have the chance to work together directly. What I took away from her comment was that the dynamics and tenor at the C-level reverberates through all of the functions.
I hope my story inspires others to embrace their career journeys and enjoy each part of the career progression for what it is. Recently one of our PMs went on parental leave and I had the opportunity to product manage a team directly for a few months (in addition to my leadership role). I jumped at the opportunity. I relished collaborating closely with our designer and engineering leads and all of the detailed decisions that leveled up to a solution we could be proud of. I got the chance to do more customer discovery, an experience which reignites my desire to connect more with the users of our platform and not just the buyers or primary champions. It solidified in my mind the differences between the levels of product management but more importantly, it reminded me that there is no one right or most desirable level, there is only love of the craft.