Looking for a job

Josh Flippance

@joshflippance

Canada

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What I'm looking for

A senior product role, Senior PM through VP, on a B2B, B2C or B2B2C SaaS product where AI is core to the strategy, not a feature added late.

Zero to one or an established product that needs a new direction. I want real ownership of the problem and the outcome, on a team where building things yourself is normal.

Remote, or hybrid in the Greater Toronto Area

B2B SaaS product management across health tech, fintech, edtech, cybersecurity, martech, and HR tech.

Built and led product and integration teams of up to 5 at IMS, ADP Canada, and MealSuite.

Owned product strategy and a $2M operating budget at Limelight, leading the core SaaS platform rebuild from concept to launch, and a portfolio of 14+ product lines contributing $5M+ ARR at Points.com.

Scaled MealSuite's integration platform to 100+ enterprise customer connections across EMR/EHR, ERP, financial, and identity systems, cutting delivery time by more than half.

Specialties:

Product Strategy & Roadmaps

Zero-to-One Product

AI Product Management

Agentic Workflows

RAG Model Evaluation & Guardrails

Human-in-the-Loop Design

Platform & API Strategy

Enterprise Integrations

Data Governance

HL7 / FHIR

Go-to-Market Strategy

Strategic Partnerships Portfolio & P&L Ownership

Team Building & Mentorship

Agile / Scrum / SAFe

Experience

Work history, roles, and key accomplishments

Director, Data Integrations

MealSuite

Jan 2025 - Jan 2026 (1 year)

Built and led a team of 5 integration professionals and delivered 100+ healthcare interoperability integrations across EMR/EHR, ERP/financial systems, supply chain, and SSO/identity platforms. Cut implementation timelines by 50%+ by standardizing HL7, API, EDI, SFTP, SAML/OIDC/SCIM integration delivery and driving AI-assisted documentation and spec workflows.

HL7 EHR Integration API Strategy EDI SFTP Data Interoperability Enterprise SaaS LLM Assisted Documentation

VP Product

Limelight Platforms

Jan 2023 - Jan 2025 (2 years)

Directed launch and commercialization of a SaaS platform from concept through market delivery, including AI-powered features for content generation, analytics, dashboards, reporting, and site creation. Managed a team of 3 product professionals and a $2M operating budget while supporting adoption across 50+ customer organizations.

Dashboarding Product Strategy SaaS Marketing AI Content Generation Product Launch Stakeholder Management Budget Management

Senior Product Manager

Covers.com

Jan 2021 - Jan 2022 (1 year)

Launched a sports data platform that improved ingestion, processing, and delivery by 150%+. Delivered automated content solutions using advanced sports statistics, picks, and predictions while managing third-party data provider relationships and roadmap execution.

Product Management Data Ingestion Sports Data Roadmapping Agile

Senior Product Manager

IMS

Jan 2020 - Jan 2021 (1 year)

Built, mentored, and coached Product Managers within the Canadian Product organization. Launched an industry-first Connected Claims solution with mobile-first FNOL capabilities, led roadmap/release planning for the IMS Mobile Platform and DriveSync, and supported the transition to SAFe.

Product Leadership Mobile First FNOL SAFe Release Management Roadmapping Agile Scrum Stakeholder Management

Product Manager, Platform Partners

Altus Group

Jan 2017 - Jan 2018 (1 year)

Led strategy and launch of a new multi-tenant cloud API platform, including Integration Partner and Certification programs. Drove platform go-to-market execution alongside roadmapping and partner enablement.

Partner Programs Go To Market Roadmapping SaaS Platforms Developer Enablement

Director, Product Management

BlueSun

Jan 2016 - Jan 2017 (1 year)

Set product strategy and roadmap for a SaaS wealth management platform and designed an MVP to consolidate five products. Drove early delivery planning to align stakeholders around the product direction.

SaaS Product Strategy MVP Development Roadmapping Requirements Definition Stakeholder Management Agile Product Delivery

Senior Product Manager, Security

Scalar Decisions

Jan 2015 - Jan 2016 (1 year)

Drove 200% YoY growth and launched Canada’s first Managed Cloud SIEM service. Owned security product roadmapping and go-to-market execution to scale adoption.

Security Product Management SIEM Managed Cloud Services Growth Strategy Go To Market Roadmapping Stakeholder Management

Senior Product Manager

ADP Canada

Jan 2013 - Jan 2015 (2 years)

Owned the product roadmap for Workforce Now and coordinated three major releases impacting 2,000+ customers. Managed release planning and stakeholder alignment to deliver enterprise-scale updates.

Workforce Now Product Roadmapping Release Management Enterprise SaaS Agile Scrum Customer Impact Management

Senior Product Manager

Invatron Systems

Jan 2011 - Jan 2013 (2 years)

Led an Agile transformation that lifted development efficiency 200%+ and improved delivery predictability. Recovered a critical release and shipped a new product in under a year through focused planning and execution.

Agile Transformation Development Efficiency Release Recovery Product delivery Cross functional Leadership Project Management

Senior Product Manager

Points.com

Jan 2007 - Jan 2011 (4 years)

Promoted from BA to Senior PM in under a year and managed 14 product lines generating $5M+ ARR. Led product execution for major loyalty partnerships and owned outcomes across the portfolio.

Product Management Revenue Growth Go To Market Agile Delivery Stakeholder Management

Product Manager

Prodigy Education

Jan 2019 - Present (7 years 9 months)

Led development of internal content management and authoring platforms supporting 50M+ students globally. Delivered a new content management system that reduced publishing timelines from months to hours and coordinated cross-functional teams across Product, Engineering, QA, and Design.

Product Management Content Management Systems Authoring Platforms Cross functional Leadership Agile Delivery Product Strategy