DIY Career Development for Startups

Josh Sassoon
7 min readMar 27, 2019

One of the benefits of joining a startup is the ability to have more varied opportunities and larger scope projects, all in a shorter amount of time compared to an established company. But the flip side is that startups don’t normally provide formal career development until they reach a certain level of organizational maturity.

In fact, there’s a tacit acknowledgement about the lack of career development resources at startups — we’re used to thinking that it’s just what comes with the territory and that you have to pull yourself up by your bootstraps when it comes to your own professional development.

But why should we accept that as a given? Just because you’ve joined a startup, doesn’t mean you’ve been relegated to the career development wild west.

Whether you’re a manager or an individual contributor, you can define your own development goals and make meaningful steps toward them in a way that mirrors what you’d expect at the bigger companies.

Over the past few years while I was working in the startup world I had the chance to build career development resources with my teams from the ground up. We didn’t do it formally (with HR) at first — it was a DIY effort. We originally did it to help our team get the development they were asking for, not because we felt titles or levels were necessary, and we did it with virtually no resources. Later on we would do a formal company-wide initiative that built on our original thinking. Below is a quick recap of how we approached providing our budding team with a career development framework.

1. Adopting criteria and building a skills matrix

Our early team was small, everyone had the same title and we didn’t have any levels. But in reality, we obviously had a variety of experience levels and competencies. We also had several people who wanted to grow into leadership roles. People were feeling frustrated that they didn’t know how to develop themselves, and that they didn’t have a way to measure their progress.

We needed to give everyone concrete ways of understanding how we could all improve, but also be realistic about the types of resources we could provide. After all, we were a startup, and our team was stretched as it was.

We started by articulating a set of criteria that we could all agree were the qualities of a great designer: impact, craft expertise, collaboration, leadership and citizenship. One of my colleagues documented these criteria in more detail in a previous post about what makes a great product designer. Even just this first simple act of writing down the criteria helped our team focus on growth areas, as well as lean into areas where they were already strong.

After we established the shared set of criteria, we drafted a “skills matrix” that showed designers how they could progress on a developmental spectrum from “budding” to “expert” on each criteria. It was basically a mini-ladder for each criteria.

The criteria and skills matrix allowed us to create actionable plans with each of our team members. It also helped put each individual’s goals into clearer focus. Some designers were more interested in craft than leadership, while others spiked on collaboration and wanted to do more citizenship work. While we needed everyone to meet a minimum-bar of excellence on each of the criteria, we wanted people to identify their superpowers and biggest development areas and lean into them more deeply.

2. Establishing career tracks

The criteria and skills matrix were a good first step, but we still had to solve the problem of giving our team clear paths they could point themselves toward. Continuing to develop individual skills didn’t add up to a holistic approach to career development. Several people wanted to pursue leadership roles, and others wanted to understand what it looked like to grow into a more senior individual contributor.

So we decided to roll out career tracks — a designer could progress on the individual contributor track to become a principal designer, or choose the leadership track and become a design lead or a people manager. We made it clear that both IC and leadership tracks were equivalent, and that pursuing leadership wasn’t “better” or more impactful in any way.

One of the best parts of this time was debunking the myth that formal leadership was more influential than being an IC. To help show the team that there was a viable career trajectory as an IC, we hosted a principal designer speaker series with a few amazing external principal designers. We also did a lot of work on recognition and feedback to make sure that people saw individual contributors being rewarded and given credit for their thought leadership in the organization.

After rolling out career tracks, we moved a few people on the team into the design lead role and added a design manager to show the team there were internal growth opportunities. It was an important moment for the team, since we were still very much doing this as a DIY effort, but still able to show that we were investing a significant amount of internal energy into our own development.

3. Building an official career development framework

Almost a year later we were able to do a formal career dev initiative as a company. Every function was asked to build career tracks and criteria at this time, and our scrappy DIY work set us up for the formal efforts perfectly. As engineering, product and all of the other functions were just starting, we’d already spent over a year building awareness and alignment around our approach.

We still had more detailed work to do, so I formed a working group comprised of designers, researchers and writers. Prior to this formal effort we’d been a team of mostly designers, so we’d really only been able to build development resources for design. By this point we had quite a few more researchers and writers, and we wanted to invest in building out their resources just as much as we had for design.

To start, we got as much reference information as we could from other companies that were willing to share their frameworks. And then we started writing our own framework in detail. Thanks to some tight deadlines from HR it took our working group just a few weeks to get our initial draft done. Once we were done, we needed to make sure it not only looked right on paper, but that it actually worked in practice.

We asked our team to do self-evaluations using the framework, and then we went through a calibration process where we matched people to the appropriate track and level. The self-assessments were also a great tool to learn about how people viewed their own strengths and areas for development.

We also realized we’d need to adjust some of our thinking. It was unrealistic to think that we’d get it right from the start, and we knew the framework would be a living document that would go through many iterations as the team and company grew. Shortly after we first applied the framework, we made some of the criteria for the senior design levels more rigorous to reflect what we saw from our more senior people in their day-to-day work.

What I learned

Looking back over the past few years, I’ve learned a lot about how to approach career development based on what the team actually needs, not based on what other teams or companies are all doing. Regardless of whether it’s a startup or a company with established career dev tools, the important thing to remember is that this is all about finding the most realistic and scrappy methods to develop yourself and your team.

It’s not about having the perfect set of resources from HR, or having formal titles or levels, although most career development frameworks do anchor on those constructs. It’s about giving people a clear sense of what skills matter on your team, giving them guidance for developing those skills, and helping them measure their progress.

I’m now working at a larger company with a well established career development framework, but that doesn’t mean my work is done and I can just lean on the existing framework and call it a day. A framework is still just that — a set of guidelines, not hard and fast rules for how to grow your people.

If you’re at a startup and you’re looking for ways to develop yourself and your team, remember you don’t have to build a formal framework overnight. In fact, you probably shouldn’t. Start small, and focus on what your team needs in the moment and work toward realistic goals, whether it’s a simple set of criteria to start, or a more robust skills matrix.

Eventually you’ll get to a more detailed set of guidelines, and perhaps even a formal career development framework. But remember the important part, which is giving your team clear and meaningful opportunities to keep growing.

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Josh Sassoon

UX lead @ Google Photos. Previously Thumbtack, YouTube, Apple, & Sony.