Challenge admin, tools so customers don't need us

Problem

Challenges worked. Running one did not.

Every challenge a customer wanted meant a request to us: someone to configure it, someone to write the invitation, someone to remember the reminders, and someone at the end to work out who had won. A feature that needs its vendor present every time it runs is a feature that runs rarely — and the value of a challenge is in repetition, which is exactly what a support queue prevents.

What I did

• Designed a creation flow the customer's own stakeholders and leaders can use: challenge type, dates, prizes, and the rules specific to that type — maximum team size for a leaderboard, and so on.
• Designed the raffle selector. Personal and team target challenges accumulate entries per participant across the run; at the end an admin draws from them and gets a winner, rather than exporting a spreadsheet and trusting it.
• Specified the email sequence to run off the challenge itself, so nobody has to remember to send anything. Creating a challenge sends the invitation with its details; reminders go out during the run; a result email closes it, naming the winning team or the raffle winner.
• Kept it to the web deliberately. This is a task someone does sitting down, once, with real attention — a phone-sized version of it would have been effort spent making a rare task portable.

Outcome

• Organizations create and run their own challenges without us in the loop.
• The communication around a challenge happens whether or not anyone remembers it, which is what keeps a month-long challenge alive in week three.
• Prize selection is a button rather than a spreadsheet and a promise.

Who did what: I led design and UI. Engineering built the tool and the automated sends; product management and leadership shaped what an admin needed to be able to configure.

Why this is its own case study: the participant experience and the admin experience are two different products with two different users, and designing the second is what made the first repeatable. Most of the value in Challenges — the 65% lift in Daily 5 completions — only materialises if a challenge happens more than once.