Improving retention with clear career paths
Supporting the team on its path from 23 to 135 designers through vertical and lateral opportunities
Context
When I arrived the 23-person team had a 3-year average tenure. They’d lost a few designers but morale was good. The team was doubling each year, so retention looked like a future problem.
The team had a flat structure with two management levels. Designers were capped at Senior with no path to Staff-level roles, causing limited career progression and unclear advancement criteria. This often relegated designers to a “junior partner” role when working with Staff PMs or Engineers.
Mobility across the team was nearly nonexistent because the contextual knowledge needed to move between areas was difficult to obtain, creating friction that slowed transitions and limited who could take on different responsibilities.
My Role
As the DesignOps Manager, I was responsible for:
Updating the career paths
With most of our managers being first-time managers, the role of Ops fell to me naturally, so I drove the writing of the career paths with an angle on clear progression paths.
Secure deployment and enablement
A key piece of this process was the ability to provide managers with proper enablement to be the guardians of these new levels.
Define governance
I established a calendar of revisions for the paths to make sure they evolved as the needs of the teams evolved. The challenge for this piece was to avoid the feeling of “moving goal posts”
Invest heavily in Managers’ Enablement
I created a “Manager’s version” document to support the new flexibility of the career paths. Just like teachers have a “Teachers’ Manual” when learning languages, this document helped managers set clear goals for each individual while ensuring fairness and equality across their teams.
Every minor or major revision was accompanied by a short 2–3 minute Loom video that explained the change to managers and outlined how it would impact their teams. These brief videos made updates easy to absorb and put practical guidance directly in managers’ hands.
As the organization grew from two levels of management (six managers total) to a five-level structure (twenty-three managers total), we maintained the commitment to enable every single manager. The combination of the Manager’s version document and the accompanying Loom videos ensured consistent support and alignment at every stage of growth.
Ran regular revisions
This was a tricky one because we needed to avoid the feeling that we were “constantly moving the goal posts.” We balanced stability with iteration so people wouldn’t feel that expectations shifted arbitrarily.
We ran minor revisions every six months, usually focused on improving language and clarity. These updates kept the guidance readable and relevant without changing the underlying expectations.
We ran major revisions every year to reflect the growth of the team and the company environment. Annual updates allowed us to address larger shifts in scope and responsibilities while giving everyone time to adapt.
For instance, when the company expanded from three products to seven, designers needed to become more platform-minded and understand end-to-end user workflows. In response, we added clearer statements that designers should think thoroughly across product workflows as part of the core skills we expect.
Approach
Give more accountability to Managers
The initial version of the career paths felt like a checklist where designers had to “complete challenges” to get promoted and managers had very little to say, because intangibles were not accounted for in the career paths. I rewrote the career paths recognizing context and qualitative contributions rather than rigid counts.
For instance, instead of asking “Designers are producing 2–3 workflows per month,” we shifted the wording to “Designers are following and even improving the delivery work of teams.”
This intentional vagueness allowed managers to adapt expectations to the rhythm of their team while keeping focus on impact and continuous improvement.
Key Takeaways