Payments Registration Mobile-First 2024

The Tournament Engine for Youth Sports

A systems-level redesign of high-volume tournament registration, bulk checkout, and payment architecture across regional and national youth sports leagues.

Role
Lead Product Designer Payments & Registration Squads
Company
LeagueApps New York City
Timeline
2024 Q1 – Q4
Methods
Discovery · Systems Design Gong · Dovetail · Figma
LeagueApps Tournament Checkout interface
00

Background

When LeagueApps underwent a company-wide reduction in force, I inherited leadership of two major product squads: Payments and Program Registration. My focus quickly shifted to the tournaments initiative — the highest-priority opportunity to capture share in the competitive youth sports market.

At the time, the platform only supported completing one team registration at a time and lacked mobile optimization. We needed to reimagine the system from the ground up: a scalable, mobile-first experience supporting bulk team registration, complex pricing logic, and seamless payments.

⚙️
Technical Context: OG → NG Migration

LeagueApps was mid-transition between its legacy (OG) and Next-Gen (NG) platform architectures. Data synchronization between the two environments introduced real complexity — requiring surgical precision in both design and engineering decisions at every step.

01

Users & Context

The LeagueApps ecosystem serves a diverse set of users, each navigating different workflows, responsibilities, and levels of technical comfort.

Tournament Organizer
Admin / Power User
  • Configure divisions, pricing, and roster caps
  • Manage waitlists and compliance flows
  • Register returning teams on behalf of coaches
  • Export data for compliance and reporting
Team Staff / Coach
Registrant
  • Register multiple teams quickly in the field
  • Select payment plan and complete checkout
  • Manage roster on a mobile device
  • Receive clear confirmation and receipts
Parent / Guardian
Registrant
  • Register a child without confusion
  • Complete payment quickly and securely
  • Receive clear confirmation of registration status
LeagueApps Sales & CS
Internal Stakeholder
  • Demo capabilities to enterprise prospects
  • Escalate organizer pain points quickly
  • Support partners during high-volume events

Internally, I worked across two product squads and multiple stakeholder groups — customer success, sales, and engineering. These cross-functional collaborations were essential to translating business priorities into a coherent user experience.

02

Problem

Core Question

How do we transform a fragmented, one-at-a-time registration system into a scalable tournament engine — without disrupting the ongoing OG-to-NG platform migration?

Tournament organizers and registrants alike struggled with a fragmented and inefficient registration process. The pain points fell into five categories:

Registration Efficiency
Each team, player, and staff member had to be registered and paid for separately — even when multiple registration types were needed in a single session.
Manual Organizer Workflows
Organizers manually handled tasks that should have been automated: adding players, managing waitlists, and enforcing roster caps.
Pricing Rigidity
No tools existed to vary registration costs by player position, role, or form response. A single flat price was the only option.
Poor Mobile Usability
Most users interacted with the system in the field and on the go, yet the interface wasn't optimized for mobile at all.
Inherited NG Debt
The in-progress NG system I inherited had its own usability and scalability gaps — addressed incrementally sprint over sprint to avoid derailing core work.

From a business standpoint, these shortcomings limited LeagueApps' ability to compete in the tournament software market — a space dominated by mobile-optimized, streamlined platforms.

03

Process

Discovery

Research began by analyzing feedback from recorded customer success and sales calls in Gong, then synthesizing insights in Dovetail. I facilitated assumption-mapping workshops and prioritization exercises to validate what we believed we knew about our users.

Assumption mapping artifact for tournament waitlists

Assumption mapping artifact from a waitlist prioritization workshop — used to surface hidden risk and align the squad before committing to design direction.

We interviewed over 20 tournament organizers plus a handful of parents and coaches. One surprising insight: organizers frequently registered returning teams on their behalf — a clear signal that the registration flow was too time-consuming for busy coaches and staff.

20+
Organizer interviews conducted
5
Core friction themes identified
2
Product squads aligned under one vision

Key Insights


Design & Strategy

With these insights, I restructured the experience around scalability and reuse — not just patching existing flows, but rearchitecting the registration model.

D-01 Introduce a bulk registration cart and simplified checkout
Why
Organizers needed to register dozens of teams in a single session. One-at-a-time checkout created compounding friction and payment errors.
Tradeoff
Cart architecture added backend complexity and required coordination across Payments and Registration squads during an already fragile migration window.
D-02 Dynamic payment plan entry — up to 12 configurable options
Why
The original structure offered a single fixed payment option. Partners needed granular control over installment schedules to serve different budget situations.
Tradeoff
More options risk decision paralysis. We capped at 12 and added smart defaults to reduce cognitive load for both organizers and registrants.
D-03 Apply Fieldhouse DS for accessibility and consistency
Why
Fieldhouse enforced WCAG 2.1 compliance across the platform. Tournaments needed to meet the same baseline — especially for mobile and form-heavy flows.
Tradeoff
Some component constraints required custom pattern work. We contributed back to the system rather than working around it.
D-04 Reduce visual clutter — open layouts over box-heavy UI
Why
The existing NG interface was dense and overwhelming. Tournament registration involves many steps and high-stakes decisions — clarity reduces error rates.
Tradeoff
Open layouts can feel less structured to power users. We used progressive disclosure to keep advanced controls accessible without surfacing them by default.

Collaboration & Handoff

I led design reviews across both squads, presenting work twice monthly to leadership and weekly to engineering. During handoff, we used boxing exercises — structured working sessions mapping each UI element to its backend endpoint — to catch mismatches early and keep velocity high.

Feedback loops were tight: constant iteration between Figma prototypes, Jira tickets, and in-progress demos kept all parties aligned without heavy documentation overhead.


Testing & Iteration

I moderated prototype walkthroughs at key decision points. The most significant early win came from a single microcopy change.

Registrants were entering parent information where tournament administrators expected child information. One field label update nearly eliminated the error entirely.

— Usability Test Finding, Tournament Registration Flow

These iterative test-and-learn cycles transformed stakeholder understanding of user testing's value — leading to broader adoption of unmoderated usability testing company-wide.

Phase 1 — Foundation
Bulk Cart & Core Registration
  • Bulk team registration cart
  • Mobile-optimized checkout
  • Roster cap configuration
  • Fieldhouse DS application
Phase 2 — Advanced Tooling
Pricing, Waitlists & Compliance
  • Dynamic payment plan builder
  • Native waitlist management
  • Position-based pricing logic
  • Automated compliance flows
04

Outcome

110%
of $3M payment goal hit before end of Q3 2024
96 teams
registered by one partner in 30 minutes
~100%
drop in form errors after microcopy update

The previous solution could take a single organizer over 8 hours to register the same number of teams. The redesigned experience compressed that to 30 minutes — a 16× improvement in throughput for high-volume events.

Beyond registration, the tournaments initiative created a roadmap for future extensibility into memberships, e-commerce, and add-ons — establishing a scalable architecture that future teams can build on.

05

Reflection

What Worked
  • Cross-squad design reviews built alignment fast
  • Boxing exercises caught integration gaps before dev
  • Incremental NG debt reduction prevented rework
  • Microcopy testing produced outsized impact
What I'd Do Differently
  • Map the full program ecosystem earlier to surface cross-program redundancies
  • Prioritize an IA overhaul alongside the visual redesign
  • Involve CS earlier in waitlist notification design

This project reinforced the importance of balancing deep collaboration with design autonomy. While constant communication across squads was time-consuming, it built the trust needed to move fast during a critical product transition.

I also learned firsthand that mobile-first thinking is non-negotiable in youth sports. Nearly every critical action — from roster checks to payments — happens on the field, on the go, under pressure.

The Tournaments initiative modernized a core LeagueApps product and catalyzed an organizational shift toward scalable, design-led systems thinking — one that continues to shape how new programs are conceived.