← Work / Midseason
Case study · Founder work
An AI-powered sports marketplace that processed $250K+ in its first 90 days.
- Strategy
- UX/UI
- Design system
- Development leadership
Midseason — the AI-powered sports marketplace
The problem
Sports organizations run on fragmented admin tools while athletes have no central place to discover events, courts or community.
My role
I owned strategy, research, UX/UI, the design system and go-to-market, and oversaw our team of developers.
Club sport runs on software that treats sport as admin work.
Organizations stitch together registration, scheduling, payments and communication from tools that were never designed for them. Athletes get the leftovers: no central place to find events, courts or community.
Midseason was the marketplace answer: one AI-powered platform connecting both sides across mobile and web. Volleyball first, on purpose — a single sport keeps the cold-start problem winnable and the product opinionated.
Every decision has two customers.
Athletes want
- Discovery — events, leagues, courts near them
- Profiles that get them seen and scouted
- Simple sign-up and payment
- Community around their sport
Organizations want
- Registration that runs itself
- Payments without the paper chase
- Insight into their leagues and members
- A pipeline of new athletes
The athlete side
Finding your sport should feel like the sport.
The problem
A plain search box over early-stage inventory returns empty results — and empty results teach athletes to never come back.
The options
Three ways to make discovery work on a young marketplace.
The call & the cost
It demos less flashily and took longer than wrapping an off-the-shelf chat UI. The win: AI that personalizes results athletes were already asking for.
Shipped
Intelligent search across events and organizations, plus map-based court and venue discovery — courts were real even before inventory was deep, so the app was useful on day one in a brand-new region.
AI that has to be discovered as a feature has already failed.
The marketplace isn’t real until money moves.
The problem
Club sport money moves through e-transfers, cheques and spreadsheets. For a marketplace, payments aren’t a feature — they’re the proof the model works.
The options
Launch free and add payments later, or carry marketplace payments from day one.
What happened
in transactions within 90 days of launch.
Organizations trusted the rails enough to move their registration revenue onto a brand-new platform — run by clubs, paid by parents, in three regions.
One system, every sport.
The design system was mobile-first and token-driven — color, type and spacing as tokens, components built once and reused across the athlete app, the organization surfaces and the web platform.
Volleyball was a theme, not a hard-coding. Expanding to the next sport meant re-theming the product, not redesigning it. Spend once, flex forever.
Built to grow with every sport it touched.
“Nathan has shown a great amount of care when it comes to our experience using Midseason. He quickly developed a deep understanding of how we operate as a league and business.”
I registered 2 spring doubles teams today using Midseason. Super easy process! Love the app!
What I learned.
- 01
Two-sided means everything ships twice
The smallest thing that serves both sides, or it doesn’t ship.
- 02
Payments-first was the right hard call
Usage can flatter you; revenue can’t.
- 03
Constraints were the best design tool
Every constraint I resented made the product more focused.
- 04
A marketplace is operations, not just product
The screens are half the job.
