Director, Product Management: AI

Employment Type:

Job Description:

AI is changing how travelers discover and buy travel. Based in Montreal, you will lead the Solutions business unit's AI product portfolio, from strategy through to products that ship and create measurable value for our partners.

What You'll Be Doing

You will define and own the multi-year AI product strategy and roadmap for the Solutions business unit, spanning agentic commerce, discovery, offer optimization and partner operations. You will turn that strategy into funded priorities, make trade-offs with executives, partners and engineering, and own outcomes including partner revenue, adoption, model quality and cost to serve. You will build a team of people who prototype and ship, hiring, developing and retaining strong product talent while removing the blockers that slow delivery. AI will be part of your daily operating model: you will use modern tools to prototype, design evaluations, test experiences and move ideas into live partner tests, working closely with AI Product Operations.

What Success Looks Like

• First 90 days: A clear, agreed AI product strategy and roadmap for Solutions, an honest assessment of the team and a hiring plan, and at least one working prototype in front of a partner.
• Six months: The team is staffed with builders and operating for speed, with clear ownership and rhythms with AI Product Operations and engineering; multiple AI products have gone from idea to live partner test in weeks.
• Twelve months: Measurable partner revenue attributable to AI and agentic channels, a maturing agent distribution footprint, and a team recognized as the center of AI product excellence at Plusgrade.

What You Bring

• 10 or more years in product, including several years leading and developing product managers or applied AI teams, ideally in a B2B or platform business.
• Hands-on experience designing and shipping ML, LLM or agent-based products that customers pay for, with a practical understanding of model drift, evaluation, hallucination, latency and cost trade-offs.
• A track record of accelerating teams, hiring and developing builders, and moving products from idea to prototype to live partner test.
• Strong commercial instincts: you connect product decisions to revenue, margin and partner outcomes, and collaborate effectively with engineering, data science, design and partner-facing teams.
• Clear, direct communication with executives, partners and technical teams. Experience in travel, loyalty, e-commerce, marketplaces or pricing is an asset but not mandatory.

Why Plusgrade

Travel is about the moments that make a journey feel personal. At Plusgrade, we build the technology that makes those moments possible, from upgrade offers and loyalty experiences to revenue tools used by 575+ airline, hospitality, cruise, rail, and financial services partners worldwide.

The work is global, complex, and rewarding. You will solve meaningful problems, take ownership from idea to outcome, and work alongside people who are smart, curious, and committed to doing great work.

We also give our teams access to AI tools and the encouragement to use them thoughtfully, to move faster, explore ideas, and build better ways of working.

We trust our teams to do their best work. That means autonomy, flexibility, and room to grow.

Come help us shape the future of travel.

What You'll Love About Us

🏦 RRSP Matching · 🏥 Comprehensive Health Plans · 📅 Flexible Paid Time Off · ✈️ Travel Experience Perk · 🧘 Annual Wellness Perk · 🚆 Commuter Perk · 🌅 Tenure-Based Work From Anywhere Program · 🍼 Parental Leave Top Up · 🌍 Adventure Pass · 🎓 Learning Allowance

Our Process

We believe every candidate deserves a fair, transparent experience, so regardless of outcome, everyone gets feedback.

Our process: Recruiter call → Team interview → Hiring Manager interview → Final Interview.

Plusgrade is an equal-opportunity employer committed to accessible recruitment. We welcome applications from all qualified individuals regardless of gender identity or expression, race, ethnic origin, creed, place of origin, age, sex, marital status, physical or mental disability, sexual orientation, or any other category protected by law. Accommodation is available upon request. We may use AI-assisted tools to help screen and assess applicants for this role. This posting is for an existing vacancy.