Felix Del Rosario is the VP of Product at The Zebra, a company that provides accessible and equitable access to insurance by enabling consumers to easily compare rates online and then purchase policies through both its website and its agency. He started as a senior software developer at Cervecería Nacional Dominicana, and later transitioned into an IT project coordinator role. Felix then moved into product management roles at Indeed.com, Small World Labs, SpareFoot, and Web.com, before joining The Zebra.
In our interview with Felix, he discusses how he leverages the co-creation model to tailor opportunities to the individual career paths of people on his team, build trust, and drive retention and business success. He also shares his approach to aligning business strategy with consumer needs.
My background in engineering and software development still helps in conversations with engineers. While I now spend more time with engineering leadership, that technical foundation helps me tackle gritty details and build trust that we understand our functional areas and can move forward together.
As product leaders, we will always push to the limit. There’s always a healthy tension between us and our stakeholders or partners. With engineering, the conversation is often about, “How much is this going to cost us?” I’m able to talk through that, thanks to my technical background.
I was also a project manager in the IT department of a previous company, and that’s how I started understanding the nuances of projects and their value. They were highly technical, but With my background, I was able to grasp both the technical aspects of the projects and the business needs. I also started to understand what things cannot fail, what things can fall apart, and which items are trade-offs..
As a project manager, I often felt frustrated leading projects with little to no business value or initiatives that were somebody’s pet project. What attracted me to product management was the ability to drive initiatives that truly mattered to the business and the consumer. As a PM, I could prioritize value and ensure alignment with business needs. Product was a nice intersection between that, my previous career, and my college education.
People care about many things, but I’ll talk about two specifically. The first is that people want to have an opportunity to challenge themselves and bring growth through the work they’re doing. At The Zebra, I allow my team to use this process. We define outcomes and define the biggest problems to solve. Outcomes generally sound like metrics or goals, and then we break those down into what keeps us from getting there.
Generally, an outcome is assigned or aligned with a large consumer need. For example, consumers want to save time and money when buying insurance policies, and we want to sell policies. How do we make both these things happen? Well, we need to figure out how to make our product the easiest to use and the one that saves consumers the most money.
The second is that people want to have a sense of ownership. In this regard, we’ve embraced the co-creation model. The traditional team model is based on defining the outcome and the initiatives with a leadership team, and then handing them off for ICs to execute on. This type of relationship between leadership and the people trying to grow their careers can be impersonal. Sure, they’ll work this way for a bit, but they’ll eventually leave. With the co-creation model, leadership sets goals and provides context from which ICs can then create customer and business value.
It definitely lends itself to more senior folks. Right now, our team makeup is more senior. We’ve implemented a scaffolding system to help guide people through different career levels, with senior team members responsible for helping more junior members get comfortable with the process.
That said, we haven’t tested it extensively with more junior staff lately. The most junior person on the product management team is a product manager — we haven’t had an associate product manager in over three years. But as we keep growing and bring new people into the fold, we’ll reassess whether our framework supports everyone’s career development
We have collaborated with our People department to create functional guidelines. Both leadership and management teams follow this framework, so everyone knows where they’re headed and why. We offer two distinct career paths — management and individual professional tracks. Everyone can choose which path they want to take when the options are available.
While management roles aren’t always available, we’ve created well-defined individual contributor paths, which are becoming more common across companies. This allows employees to choose a path that aligns with their aspirations when the opportunity arises. The framework provides clarity on the next steps, what’s needed to progress, and how to collaborate with managers to achieve those goals. We aim to have monthly check-ins with employees, conduct a full evaluation every quarter, and align with the company’s biannual review cycles. This structure helps keep people engaged and focused on their growth.
I refrain from calling it a “career ladder” — I prefer calling this “career progression” instead. This progression is very clearly defined at both The Zebra and within my team. It is especially helpful for junior team members, as middle- to senior-level relationships are highly collaborative. It’s a relationship-driven approach, where everyone’s trying to help move the team forward, and junior people are equally incentivized to seek our support and advance.
I’m a big advocate of documenting everything. Even though I spend a lot of time talking about it and repeating it in meetings, my first step is always to write things down. I start with the key takeaways I want people to have — usually in the form of three to five bullet points. Then, I get feedback from the exec team and our CEO to ensure alignment, flesh out the details, and create a document I can reference whenever needed.
I have regular touchpoints with my leadership team, and I start by sharing the vision with them. From there, we hold product development town halls, which include engineering and data teams, where I outline our focus areas. This way, everyone hears the same message at the same time. I also spend additional time with the product managers to discuss their specific responsibilities and expectations.
Even though we have a 20-person team, we’re not multi-layered. The product managers, designers, SEO analysts, and others are all just one level removed from me, so it’s relatively easy to keep communication clear and direct. We have monthly all-hands meetings, during which the product team reiterates our focus and our progress.
Since we have more senior folks on the team, the first step is to simply trust that they can take on sizable projects and break them into manageable parts. That means that we need to promote accountability and trust as a team. These folks also need to have a good understanding of exactly what they’re marching toward.
We use a couple of tools and services to manage this. I have 1:1s with my leadership team, so I can keep track of everything. However actual empowerment comes from making it clear that each team member owns their project and is expected to deliver results. To get into the details of what that looks like every week, they collaborate with engineering, design, and other stakeholders to create solutions to the problems they’re talking about. It’s their responsibility to ensure that brainstorming sessions happen and that the product moves forward.
That sense of ownership drives retention because, in my opinion, the excitement of knowing that business leadership has trusted you to deliver on a particular outcome is huge. It keeps people on. That process of co-creation, delivering on our business needs, etc., is a big driver of retention.
Additionally, we focus a lot on our consumers — what they want, need, and even what they don’t yet know they want but that we can deliver. Our team members joined The Zebra to solve consumer problems, and I work to create feedback loops where they can see how their work impacts people. Whether it’s through reviews on platforms like Trustpilot or direct feedback, knowing that the product is making a difference in consumers’ lives adds a meaningful dimension to a PM’s work, which further supports retention.
We listen to customer support calls, conduct interviews with both consumers and customers, and closely read their emails to understand their pain points and feedback. We also conduct user testing. While user testing is primarily focused on specific product features, it often leads to broader insights as users share their thoughts on other aspects of the product during the process. We help permeate what we’re hearing and experiencing with our consumers to the rest of the company.
We also have brainstorming sessions with the engineering and design teams and other stakeholders. Eventually, we intend to invite actual customers to the brainstorming meetings as well. We’re getting closer to making that happen, and I believe it could be a game-changer in keeping us close to the voice of the customer.
We do two company-wide reviews each year, and during the annual review, we include upward feedback, too. Everyone on my team gets to provide feedback on their managers, and managers give feedback on me. There’s also the option to provide feedback on skip levels. A couple of the leaders on my team also run what they call “pulse checks” — ad hoc check-ins with the team that work like upward feedback.
We also have weekly 1:1s between managers and individual contributors. I use this model called the SOON funnel (success, obstacles, options, and next steps), and I reference it before each session. It’s written into every 1:1 doc and helps unlock any challenges in the manager-managee relationship.
Our performance reviews are also closely tied to our company values. People are asked, “How does this person embody values A, B, C, and D? Can you provide specific examples?” For example, two of our core company values are candor and accountability, and we ensure they’re not just fluff. We also use emoji reactions to represent each of the values on Slack — that helps us remember to live by them day-to-day.
We have the primal rewards — salary changes, promotions, etc. But we also have a gratitude channel, where team members publicly acknowledge each other’s efforts and celebrate the outcomes they’ve achieved together, especially when solving consumer needs. I also make it a point to express gratitude publicly, ensuring people feel recognized for their hard work.
We’re not just here to do the bare minimum — we’re working to make insurance more accessible and equitable for everyone. Helping people find the best insurance for their needs is a deeply rewarding goal. And giving people the autonomy to shape how we get there adds an extra layer of fulfillment for the team.
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