Product Leader · AI Builder

Josh FlippanceProduct Leader and AI Builder

I build products. Now I build them with AI.

I take complex products to market. Strategy, roadmaps, and launches shipped across multiple industries in both B2B and B2C SaaS, including 100+ enterprise integrations where the data is regulated and nothing is allowed to break. I never stopped building, and today I direct AI coding agents to take a product from idea to a real release.

Open to Senior Product Roles and AI advisory for companies building or scaling with AI.

Burlington, ON

Portrait of Josh Flippance
40+ Products Shipped50M+ Users Reached$5M+ ARR Managed100+ Integrations200% YoY Growth7+ Industries
Roles acrossMealSuiteLimelight PlatformsCovers.comIMS (Insurance and Mobility Solutions)Prodigy EducationScalar DecisionsADP CanadaPoints.comADESA Canada

A builder who became a product leader

I began my career writing code, moved into business analysis, and grew into senior product leadership. Along the way, I led cross-functional teams managing budgets in the millions, contributed to multi-million-dollar ARR, and improved operational efficiency across a range of SaaS industry verticals, including healthcare, fintech, edtech, and cybersecurity.

The developer never left. I still get into the details, sketch the data model, and build the prototype myself. That is why AI clicked for me. I use it to research, design, and ship products end to end, and I bring the same discipline to how teams scope, evaluate, and release.

AI is also my day-to-day product operating system. I use it to synthesize research, draft and iterate PRDs, pressure-test roadmaps, and build prototypes before engineering sees a ticket. When I lead teams, I apply the same AI product discipline: scope what actually needs an LLM, evaluate model and prompt output against real cases, route the right model to the right task, and keep a human in the loop anywhere a bad output has real cost.

Product Leadership

Strategy, roadmaps, and scaling products from zero to one across regulated B2B and B2C SaaS.

Data Integrations & Interoperability

HL7 and EHR, APIs, and platform integrations at scale.

AI Product Builder

Directing AI coding agents to design, build, and ship production-ready products solo.

Go-To-Market & Growth

Commercialization, product-led growth, and partner ecosystems.

  • AI Product Management Certification, Product School
  • Graduate Master Certificate in Business Analysis, Schulich
  • Certified Agile Product Owner, Scrum Alliance
  • Computer Science Technology Diploma, Sheridan College

Experience

Building products across B2B and B2C SaaS and regulated industries.

Domain
Capability

MealSuite

2025-2026

Integrating senior-living clinical and partner feeds is complex, costly, and slow to deliver.

100+ Integrations · 50%+ Faster Delivery
  • Healthcare
  • Data Platforms
  • Integrations
View case study

Limelight Platforms

2023-2025

Brands needed one platform to run experiential marketing programs end-to-end with full CRM integration.

100+ Brands · Months to Days
  • MarTech
  • 0-to-1
  • AI/ML
View case study

Covers.com

2021-2022

Data throughput limited how fast and how deep sports content could be published.

+150% Data Speed and Volume
  • Data Platforms
  • Consumer
  • Integrations
View case study

IMS (Insurance and Mobility Solutions)

2020-2021

Auto insurers wanted claims to start the moment a crash happened, not days later.

Industry First · Team of 5 PMs
  • Fintech
  • 0-to-1
View case study

Prodigy Education

2019

Curriculum content updates took months to reach millions of learners.

50M+ Students · Months to Hours
  • Edtech
  • Growth
  • Integrations
View case study

Altus Group

2017-2018

Partners had no supported way to build on the platform.

Partner Platform Launched
  • Data Platforms
  • 0-to-1
  • Integrations
View case study

Scalar Decisions

2015-2016

A security services business needed productized offerings to grow.

200% YoY Growth
  • Cybersecurity
  • 0-to-1
  • Growth
View case study

ADP Canada

2013-2015

A large HR platform needed a roadmap that moved thousands of customers forward.

2,000+ Customers · 3 Releases
  • Fintech
  • Growth
View case study

Points.com

2007-2011

Loyalty currency commerce needed new revenue-generating products.

$5M+ ARR · 14+ Product Lines
  • Fintech
  • Growth
View case study

Earlier: ADP Canada, Invatron, BlueSun, Altus Group

Full history on LinkedIn

Products

Solo-built products, shipped by directing AI.

Anyone can prompt a chatbot. These are working products. The usual path takes a staffed team, designers, front end, back end, QA, release engineering, and a run of sprints. I built these solo by directing AI coding agents, and the first market-ready build of Fairway was in front of testers in under a business day.

This is my operating model, not a side hobby. One product leader, directing agents, taking an idea to a real release: architecture, auth, data model, observability, and an automated pipeline to the app stores. It is the same speed I bring to the teams I work with.

Fairway

In testing (TestFlight and Google Play)

Product lead and AI orchestrator, no hand-written code

Groups still keep score on one paper card, then someone has to add it all up and retype it into an app afterward.

0→1 Shipped
  • MarTech
  • Consumer
  • AI/ML
  • 0-to-1
View case study

Sidekick

In Google Play testing

Product lead and AI orchestrator, no hand-written code

AI job-search tools embellish. Candidates need tailoring that stays true.

0→1 Shipped
  • Consumer
  • AI/ML
  • 0-to-1
View case study

AI Mapping Copilot

In progress (research and design)

Solo product lead, research through architecture

Post-acute-care SaaS can't afford six-figure legacy EHR feed integrations.

In Progress
  • Healthcare
  • AI/ML
  • Integrations
View case study

Operating Model

Case study: the agentic pipeline I run on myself

Most PMs who say they use AI mean they prompt a chatbot. I design and run agentic systems. To prove it, I turned my own job search into one and ran it on myself for months.

This is dogfooding. Before I ask a team to trust an autonomous loop, I run one where a bad output costs me, not a customer. It runs the whole search end to end across real tools, with memory that compounds. Same way I build product: find where AI earns trust, keep a human in the loop where it matters, and redesign the workflow instead of bolting AI onto the side.

Source & discover

Searches the web and job boards for roles matching a multi-lane target, not one keyword. Normalizes every posting into one schema.

Screen & score

Scores each role for fit, flags stretch vs. strong matches, and filters out noise before I spend attention.

Tailor per role

Generates a role-specific resume and cover letter for every posting from a bank of my own pre-approved answers. Auto-names and exports to PDF.

Apply & track

Keeps a live board as the single source of truth, with every opportunity tracked across stages, follow-ups, and next steps updated automatically.

Outreach & inbox

Drafts recruiter and hiring-manager outreach and tracks headhunter follow-ups as their own pipeline.

Interview prep

Assembles role-specific prep, including an AI-fluency reference before technical screens.

Learn & persist

Writes durable memory between sessions and logs finished answers back to the bank. Each cycle runs faster than the last.

Orchestrate

Runs scheduled tasks and chains tools end to end. Self-corrects when a connector goes offline, then reconciles later.

Runs on

Web automationGoogle DriveNotionEmailLocal diskPersistent memoryRetrievalHuman-in-the-loop reviewScheduled tasks

The real shift with AI is upstream of what ships. It changes how the work gets made. So I built the proof on myself instead of putting it on a slide. This is what an AI-native PM looks like in practice: clear stages, real tool orchestration, memory that compounds, and a human in the loop where accuracy matters.

How I Work

A structured product lifecycle, start to finish

This is the operating model I run whether I am leading a product org or inside a short engagement. Six phases, each with a question it has to answer and an output the team can hold me to. It is built to kill weak bets early and get the strong ones in front of real users fast.

  1. Phase 01

    Discover

    What problem is real, and who has it?

    Customer interviews, support and sales signal, usage data, and competitive teardowns. AI helps me synthesize hundreds of inputs into themes in hours instead of weeks, then I pressure test the themes with real users.

    • Customer and stakeholder interviews
    • Usage and funnel analysis
    • Market and competitor teardown
    • Opportunity sizing

    Output A ranked problem set with evidence behind each one

  2. Phase 02

    Define

    What are we betting on, and how will we know it worked?

    I turn the chosen problem into a crisp bet: target user, outcome, success metric, and the constraints we refuse to break. This is also where I decide what genuinely needs AI and what is better solved deterministically.

    • Product strategy and positioning
    • PRD with scope, non-goals, and risks
    • Success metrics and guardrail metrics
    • Build, buy, or model decision

    Output A one page bet the whole team can repeat back

  3. Phase 03

    Design and prototype

    Does the solution hold up when someone touches it?

    Flows and interface design with the team, then a working prototype rather than a deck. I direct AI coding agents to stand up something real in days so we learn from behaviour, not opinions.

    • Journey and flow design
    • Clickable or functional prototype
    • Usability sessions
    • Technical spike on the risky part

    Output A tested prototype and a validated or killed bet

  4. Phase 04

    Plan and build

    What is the smallest version worth shipping?

    I slice the bet into releasable increments, sequence them with engineering, and stay in the build daily. Scope moves, dates get defended with tradeoffs, and quality gates are agreed before the first ticket, not after the first bug.

    • Roadmap and release slicing
    • Estimation and sequencing with engineering
    • Data model and integration design
    • Evals, review gates, and QA plan

    Output A sequenced plan and a build the team can defend

  5. Phase 05

    Launch

    Is the market ready, not just the code?

    Launch is a cross functional event. Pricing, packaging, enablement, docs, support readiness, and a staged rollout with a rollback path. Shipped means in customers' hands with telemetry, not merged to main.

    • Go to market plan with sales and marketing
    • Pricing and packaging input
    • Beta, staged rollout, and feature flags
    • Instrumentation and dashboards live at launch

    Output A release customers can buy, use, and get supported on

  6. Phase 06

    Measure and iterate

    Did it move the metric, and what do we do next?

    I read the data against the metric we named in Define, talk to the users who adopted and the ones who did not, then decide to double down, fix, or sunset. Nothing stays on the roadmap out of politeness.

    • Adoption, retention, and outcome review
    • Qualitative follow up with users
    • Backlog reprioritization
    • Scale, fix, or sunset decision

    Output An evidence based next bet, and one fewer thing to maintain

How an engagement runs

Compressed into a working sequence when I come in from the outside.

  1. 01

    Frame the bet

    We name the outcome, the user, and the metric that would prove it worked. If a feature does not need an LLM, I say so.

  2. 02

    Prove it in a prototype

    I direct AI coding agents to build something real in days, not a deck. You interact with it before anyone commits a sprint.

  3. 03

    Design the guardrails

    Evals against real cases, review gates where a bad output has cost, and a deterministic path for anything regulated.

  4. 04

    Ship and instrument

    Auth, data model, observability, and a release pipeline. Shipped means in users' hands with telemetry, not merged.

  5. 05

    Hand it to the team

    I leave behind the workflow, not a dependency: how your team scopes, evaluates, and releases AI features on their own.

Principles I hold across every phase

Scope before you build.

Decide what actually needs an LLM, and what doesn't.

Keep humans in the loop.

Reviewable, versioned outputs and approval gates, especially in regulated domains.

Evaluate like a product, not a demo.

Test model and prompt output against real cases before it ships.

Build the workflow, not just the feature.

Bring AI into how the team researches, specs, prototypes, and ships.

What I believe

Most AI projects die between demo and production.

The prototype is the easy part. What kills it is undefined evaluation, no owner for bad outputs, and integration work nobody scoped.

AI changes how the work gets made, not just the feature list.

The biggest gains I have seen come from rebuilding the research, spec, and prototype loop, upstream of anything customers see.

In regulated domains, determinism wins.

Let the model produce reviewable artifacts. Let deterministic code run against live data. That is how you get AI leverage without AI risk.

Tools & Technology

AI I build with
Claude / Claude CodeGitHub CopilotLovableClaude API
AI I run product work with
ChatGPTGeminiGranola
Product & delivery
JiraConfluenceClickUpNotionFigmaMiro
Technical & integration
React / React NativeNodeNext.jsSupabaseGitHubCI/CDHL7 / FHIRREST APIs

Work With Me

I help teams solve real problems with AI, and ship products that get used.

Two ways to work together, and I'm open about both.

Full-time leadership. I'm looking for a senior product role, Director or VP, at a company that wants a practitioner who ships, not a manager who only reviews.

AI advisory and engagements. I take on a small number of engagements: AI product audits, agentic build work, data integration architecture, and fractional product leadership for teams past the AI hype stage.

We scope the problem together. If the AI work is not worth doing, I will tell you that.

AI Product Audit

A clear read on whether your AI bet is real, and what it takes to ship it.

  • Review the use case, data, and current prototype
  • Where an LLM earns its place, and where it does not
  • Risk, evaluation, and compliance gaps

You getA written recommendation with a scoped path to production.

Timeline · 1 week

Let's talk

AI Product Sprint

From idea to a working AI prototype, fast.

  • Research
  • PRD + metrics
  • AI-directed prototype

You getA working prototype your team can click, plus the spec behind it.

Timeline · 2 to 3 weeks

Let's talk

Fractional AI Product Leadership

Senior product horsepower, part-time.

  • Strategy + roadmap
  • Embedding AI into how teams ship (feature scoping with LLMs, evals, responsible-AI)
  • Cross-functional leadership

You getA roadmap that ships and a team that can run it without me.

Timeline · Ongoing

Let's talk

Build-with-AI Enablement

Ship from zero to one by directing AI, like Fairway and Sidekick.

  • Stand up an AI-augmented build pipeline
  • Coach the team

You getYour team building and releasing with agents, end to end.

Timeline · Project-based

Let's talk

References

What people I have worked with say

Recommendations from clients and leaders I reported to, quoted as written.

It was a privilege to have Josh on my team as VP of Product at Limelight. He successfully navigated highly complex stakeholder environments with creative problem-solving, always delivering beyond expectations even under extreme pressure and budget constraints. I highly recommend him to any company looking for a collaborative, high-impact product leader.
Terry FosterChief Executive OfficerJosh's manager at Limelight Platforms
I worked with Josh while he was VP Product at Limelight Platforms, on the strategy behind rebuilding their core SaaS platform from the ground up. What I saw in that work was someone who could set direction and hold it. He made a clear case for retiring the old system rather than patching around it again, then translated that into a roadmap the whole team could execute against.
Nathan Tran TrinhAI, Data and CX Modernization LeaderJosh's client at Limelight Platforms
Every day Josh brought great insight, dedication and a commendable level of professionalism to the very challenging role of Senior Product Manager at Points.com. His mandate to oversee and grow a very large and diverse portfolio of global SaaS offerings was a hard one, which he fulfilled with excellent and unwavering attention to his clients.
Simon BrightmanChief Product Officer, RuntimeAISenior to Josh at Points.com
Josh is a highly talented, creative project owner. He dove into one of the most complex developments at ADP with enthusiasm. His many years in software development product ownership were a huge asset. Very organized and methodical in his approach to massively complex projects, taking initiative from day one.
Charles DimovMarketing Professor and CMOSenior to Josh at ADP Canada

Let's Connect

I'm open to senior product roles and a small number of AI advisory engagements. If you're building with AI, or working out whether you should, book a free 30 minute call and we'll scope it.

Want a copy of my CV? Send me a message below and I'll reply with one.

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Burlington, ON