Building AI products end-to-end

Josh Flippance

Senior Product Leader — AI-Powered Products, Strategy & Go-To-Market

20+ years building and scaling SaaS products — now building AI into how product gets done.

Burlington, ON

About

Product strategy, shipped with AI in the loop.

Product leader with 20+ years building, launching and scaling software across healthcare, senior living, cybersecurity, insurance, education and SaaS. I set product strategy, lead roadmaps and cross-functional teams, and drive products from concept through commercialization. I use AI heavily in day-to-day product work — research, PRDs, prototypes, data analysis — and apply AI product discipline: scoping which features are worth building with LLMs, evaluating model and prompt output, and designing for responsible-AI trade-offs. Most notably, I direct AI to design, build, and ship real products end-to-end as a solo non-engineer.

  • AI Product Management Certification – Product School
  • Graduate Master Certificate in Business Analysis – Schulich
  • Certified Agile Product Owner – Scrum Alliance

AI Projects

Real products, designed and shipped by directing AI.

Statuses are accurate as of 2026 — apps are in active testing; the Integration Copilot is at the research and design stage.

Fairway

In testing (TestFlight & Google Play)

AI-Built Cross-Platform Golf App

Solo-built and shipped a cross-platform golf app (web, iOS, Android) as a non-engineer, directing AI coding agents (Claude Code) as the entire development team — from architecture to app-store submission. Its core AI feature turns a photo of a paper scorecard into structured hole-by-hole scores via Claude vision, plus real-time multiplayer group scoring.

  • React / TypeScript
  • Node
  • Supabase
  • Capacitor
  • Claude Vision
  • Sentry
  • PostHog
  • Playwright
  • GitHub Actions
  • Codemagic → TestFlight

Sidekick

In Google Play testing

AI-Powered Job-Search App

Land your next job — the honest way.

Founder & builder — product, design, and full build

Sidekick tailors your résumé and cover letter to a specific job using only what's true about you, with an 'honesty guardrail' that fact-checks every output so nothing is invented. It also walks users through a guided, adaptive intake that builds their brand, résumé, LinkedIn profile, and a job-search plan — then tracks every application.

  • Résumé + cover-letter tailoring with an AI verification pass that flags anything unsupported
  • Adaptive, one-question-at-a-time intake wizard that reshapes based on your answers
  • Saved-roles tracker (drafted → applied → interviewing → closed)
  • Google + email sign-in, cross-device sync
Sidekick app icon
Sidekick home screen
Sidekick apply to a job screen with honesty check
Sidekick guided get-ready intake wizard
Sidekick my roles application tracker
  • React Native (Expo)
  • Next.js / Vercel
  • Claude API (Sonnet + Haiku)
  • Supabase (Auth, Postgres/RLS)

AI Mapping Copilot

In progress (research & design)

Healthcare EHR Integration

As a solo PM directing AI, I self-initiated a healthcare data-integration product and ran the full front end of product development — market research, PRD, competitive analysis, and architecture — end-to-end without a team. AI research across ~40 cited sources identified a specific whitespace: sub-$30K legacy-feed integration for post-acute-care SaaS. I designed a healthcare-safe architecture where the LLM produces reviewable, versioned mapping artifacts behind a human-in-the-loop approval gate and a deterministic runtime — no AI on live clinical data.

  • Claude / Claude Code
  • HL7 v2
  • EHR / EMR
  • Human-in-the-loop
  • Deterministic runtime

AI-Augmented Job-Search System

Personal system

An AI agent system that runs an end-to-end job search — automated role sourcing and screening, tailored résumé and cover-letter generation, outreach drafting, a persistent memory layer, and a live analytics dashboard — orchestrating multiple LLMs and connected tools.

  • Claude
  • ChatGPT
  • Gemini
  • Google Workspace
  • Automation

Experience

20+ years leading product across B2B & B2C SaaS and regulated industries.

  • Limelight PlatformsVP Product2023–2025
  • MealSuiteDirector, Data Integrations2025–2026
  • Covers.comSenior Product Manager2021–2022
  • IMSSenior Product Manager2020–2021
  • Prodigy EducationProduct Manager2019
  • Points.comSenior Product Manager2007–2011
  • EarlierScalar Decisions, ADP Canada, Invatron, BlueSun, Altus Group
Full history and detail on LinkedIn

Contact

Let's talk about building AI products that actually ship.

Burlington, ON