Admin theme editor before the migration — inconsistent patterns, harder to maintain
Building the team, systems, and product foundations Teachable needed for its next stage of growth.
Over 3.5+ years at Teachable, I grew the design team 3× as the business scaled from $15M to $60M ARR. Along the way, I built the foundations the team needed to scale, led through an overnight shift to remote work during COVID, and ultimately led Design through the company's acquisition by Hotmart.
One of the biggest challenges during that growth was that the product and frontend foundations hadn't kept pace with the business. We were duplicating work across Design and Engineering while simultaneously preparing for a frontend migration and company rebrand. Rather than treating those as separate projects, we used the moment to rethink how they could work together.
As Teachable scaled, Design and Engineering were increasingly duplicating effort — different teams solving the same interface problems slightly differently, with no shared foundation to build on. That inconsistency was compounding as fast as the business was growing, and it was starting to show up in both the product and in how much rework each new feature required.
By early 2021, that gap had become a real business problem, not just a design tidiness problem: Product and Engineering leadership agreed we needed to address years of accumulated tech and UX debt before it got more expensive to fix.
I was part of the decision to dedicate roughly three quarters to migrating our frontend rather than continuing to build new features on the old one. That's a real tradeoff — three quarters of slower visible output — and I helped make the case for it by tying the migration to work that was tightly coupled with the Design System build-out, so the investment paid off in more than one place at once.
Making that case meant being honest with Product about what we'd be giving up in the short term, and specific about what it would buy us: faster future delivery, fewer inconsistencies for users to run into, and a foundation the rebrand could actually sit on top of.
The frontend migration, the design system, and the company rebrand could have been run as three separate initiatives. I pushed to run them as one coupled effort instead, because doing them in isolation would have meant redoing work: a rebrand without a design system underneath it would have meant re-touching every screen twice, and a design system without the frontend migration would have had nowhere real to live.
Admin theme editor before the migration — inconsistent patterns, harder to maintain
The same experience after the migration and design system work landed together
Alongside this, I grew the design org from a centralized team of 2 to a team of 10. Scaling headcount that fast only works if you're also building the operating structure underneath it — I built the career frameworks and design operations that let the team keep a consistent bar for quality as more people, and more parallel work, came into the org. In 2021, that included hiring a dedicated Design System team of 1 visual designer and 2 frontend developers, which is what made the migration itself tractable and measurable.
As of September 2021: 695 components imported into the new system, 55 created net-new.
The color audit that started this: roughly 50 near-duplicate shades of our brand green were in use across the product, with no single source of truth.
Form field anatomy from the system — the level of specificity Engineering needed to stop rebuilding the same field types differently.
The simplified palette after the audit and rebrand — from ~50 shades of green down to a defined, documented scale.
In May 2020, Teachable rebranded — moving from a look created in the company's early days to something that better matched who our creators were and where the company was headed. That rebrand started on our marketing site and collateral, and in late 2020 began moving into the product itself through the design system, which is what let it actually stick rather than existing only on the homepage.
Teachable.com before the rebrand
Teachable.com after the rebrand
My 3.5+ years at Teachable were ultimately much bigger than any one project. I joined a growing company, scaled the design team 3× as the business grew from $15M to $60M ARR, and had to keep changing how I led as the company changed around us.
Some of those changes were planned. Others definitely weren't. When COVID took us from working together in an office to fully remote almost overnight, I quickly adapted our team rituals to keep people connected and morale up. We kept the team intact through the transition while continuing to grow and ship.
By the time I left, we'd built a much more mature design organization and I had led the team through rapid growth, a pandemic, and ultimately Teachable's acquisition by Hotmart. What I took from that experience wasn't a particular framework or process. It was learning that the way you lead has to keep evolving with the people, the business, and whatever gets thrown at you.