Trilo: Full-Stack SaaS for Sports League Automation

Executive Summary

Built a full-stack SaaS product from 0→1: a Discord bot automating fantasy football league management (reducing commissioner workload from 3+ hours/week to under 5 minutes) plus a conversion-optimized marketing site with Stripe payments and Discord OAuth. End-to-end ownership from AI feature development to user acquisition funnels.

The Problem

Running a fantasy football dynasty league on Discord is operationally brutal.

• Administrative Burden: Commissioners spend 3+ hours weekly creating matchup channels, tracking records, and managing team rosters manually.
• Commissioner Burnout: High friction causes 40%+ of leagues to fold within two seasons due to organizer fatigue.
• Fragmented Tools: Existing solutions either require external websites (friction) or charge per-league pricing ($15-35/league), making multi-league management expensive.
• No AI Integration: Manual schedule entry from game screenshots is tedious and error-prone.

The Solution

I built two interconnected products that form a complete SaaS business:

1. Trilo Bot (Discord)

An intelligent Discord bot that automates league operations through slash commands. Commissioners interact where their community already lives. No external tools required.

2. Trilo Website (React)

A marketing site that handles user acquisition, Discord OAuth authentication, Stripe payments, and license key delivery via Discord DM.

System Architecture

The platform is fully event-driven across both products, with shared state in Supabase.

Data Flow

1. Acquisition: User visits trilo.gg → authenticates via Discord OAuth
2. Conversion: Stripe checkout creates subscription → webhook fires
3. Fulfillment: License key generated → delivered via Discord DM
4. Activation: User runs /admin activate in Discord → bot validates against Supabase
5. Usage: Bot handles all league operations, storing data in PostgreSQL

Key Features

AI-Powered Matchup Creation

The flagship feature: upload a schedule screenshot and Trilo extracts team matchups automatically.

COMMAND PREVIEW

D

(C) DucksToday at 11:55 AM

used /matchups create-from-image

category_name: Week 5image1: schedule.JPGgame_status: True+2 more

T

TriloAPP

Today at 11:55 AM

Thinking...

Scanning matchups...

TRILO ACTIVATED

Technical Implementation:

• OpenAI Vision API (gpt-4o-mini) processes images with structured JSON schema enforcement
• 95% extraction accuracy achieved through prompt engineering
• Cost-optimized: ~10x cheaper than GPT-4 Vision with comparable results

Discord-Native Operations

Everything happens where the community lives. No external dashboards.

Command Groups:

• /teams - Assign users to teams, view rosters, auto-updating list embeds
• /matchups - Create game channels, sync records, AI schedule import
• /attributes - Award points, approve upgrades, track spending
• /settings - Configure roles, channels, league type (CFB/NFL)

Reaction-Based Game Status

Single-tap interactions for marking games complete.

Conversion-Optimized Website

UX Decisions:

• Discord OAuth pre-checkout reduces friction
• License key delivered via Discord DM (arrives where they'll use it)
• Interactive setup guide with progress tracking

Technical Stack

Key Product Decisions

This table represents the core PM thinking behind the product. It weighs trade-offs and makes defensible choices.

Database Architecture

A critical technical decision: supporting both SQLite (local dev) and PostgreSQL (production) through a unified abstraction layer.

Why This Matters:

• Local dev: Zero setup friction with SQLite. Just run python -m src.bot
• Production: PostgreSQL with connection pooling (2-10 connections) for concurrent Discord servers
• Abstraction: Auto-converts ? placeholders to $1, $2 for PostgreSQL

Schema Design

server_settings     → Per-guild configuration
cfb_teams/nfl_teams → Team assignments (user_id, team_name, server_id)
cfb_matchups        → Matchup data with game status tracking
attribute_points    → User balances (available, total_earned)
attribute_requests  → Pending upgrades with approval workflow
server_subscriptions → Subscription status, expiration, license keys
command_usage       → Analytics (timestamp, execution_time, success/failure)

User Journey & Conversion Funnel

Funnel Stages:

1. Awareness: User lands on trilo.gg via Discord community referral
2. Consideration: Explores features page, interactive setup guide
3. Conversion: Connects Discord, completes Stripe checkout ($69.99/year)
4. Fulfillment: Webhook generates license key → DM'd to user
5. Activation: /admin activate TRILO-XXXX-XXXX-XXXX in their server
6. Retention: Daily bot usage for league operations

Impact & Metrics

Competitive Analysis

Positioning: Only solution combining AI automation with flat-rate multi-league pricing.

Challenges & Learnings

Challenge 1: SQLite → PostgreSQL Migration

• Problem: Started with SQLite; needed production-grade database
• Solution: Built abstraction layer that auto-converts query syntax
• Learning: Would start with PostgreSQL from day one in future projects

Challenge 2: Discord's 3-Second Interaction Timeout

• Problem: AI operations exceed Discord's response window
• Solution: interaction.response.defer() for long operations, then followup.send()
• Learning: Always design for async-first in chatbot architectures

Challenge 3: License Key Delivery UX

• Problem: Email delivery adds friction; users might not check email
• Solution: Discord OAuth + DM delivery-key arrives where they'll use it
• Learning: Deliver value in the channel where users already are

Challenge 4: Pricing Strategy

• Problem: Per-league pricing is industry standard but punishes power users
• Solution: Flat rate for 3 servers-competitive moat for multi-league commissioners
• Learning: Understand user behavior (2-3 leagues typical) before pricing

What I'd Do Differently

• Start with PostgreSQL: Avoid migration complexity
• Add analytics earlier: No conversion tracking currently. I would add GA/Mixpanel from day one
• User interviews before building: More upfront research on pricing sensitivity
• Build webhook monitoring: Dashboard for Stripe webhook failures

Skills Demonstrated

Links

• Live Site: trilo.gg
• Discord Bot: Invite Link
• Support Server: Join