Full-Time | Remote (Canada) | Must be legally authorized to work in Canada

About TravelAI & Traveler.md

TravelAI builds AI-powered travel products and infrastructure for a network of travel brands and booking platforms. Traveler.md is our portable, traveler-owned memory file: travelers build it once, and it carries their preferences, loyalty programs, and trip context into any AI assistant, booking platform, or travel brand they choose to connect it to. Traveler.md is live today in public beta, and this role sits at the center of turning that platform into real, everyday products across TravelAI’s network.

Role Summary

TravelAI is building a new generation of AI-powered travel products designed to make travel more personalized, useful, and trustworthy.

We are looking for a Product Manager to work alongside our Director, AI Products & Personalization and help turn our Traveler.md platform into real, consumer-facing products and experiences. The core focus is advancing personalization across TravelAI's consumer-facing brands, think property tiles, property feeds, search, property discovery, and recommendations, as well as personalization within Traveler.md itself. This may also include supporting the integration of Traveler.md into TripDesk and our existing travel distribution network, though that build-out will be led by others; this role's focus is the consumer-facing personalization work.

This is a hands-on individual contributor role for someone who can move comfortably between product discovery, requirements, design, technical discussions, and delivery. You will work closely with developers to take ideas from an early concept through implementation, launch, and iteration.

You will not simply manage an existing backlog. You will help determine what should be built, define how it should work, and maintain a high standard for the final experience.

The right person will be extremely detail-oriented, autonomous, highly proactive, and comfortable taking meaningful ownership. You should also have strong design instincts and good product taste, with the ability to recognize when an experience is intuitive, useful, and ready for customers.

What You’ll Do

Build Products on Traveler.md

- Help define and deliver products, features, and experiences built on top of the Traveler.md platform
- Support the rollout of Traveler.md capabilities across TravelAI's consumer-facing brands and sites, and help support (but not lead) the integration of Traveler.md into TripDesk
- Identify practical ways to turn platform capabilities into useful traveler and business outcomes
- Work with development teams to move initiatives from concept through launch and continued improvement

Personalization and Traveler Experiences

- Own and shape personalization initiatives across TravelAI's consumer-facing brands, including property tiles, property feeds, search, property discovery, recommendations, traveler preferences, and other customer experiences
- Translate traveler context and behavioural signals into clear product opportunities
- Balance personalization, usability, business value, and traveler trust
- Use customer feedback, product data, and judgment to improve experiences over time

Product Discovery and Definition





- Investigate product opportunities through research, internal discovery, customer feedback, data, and experimentation
- Turn broad ideas and ambiguous problems into clear product direction
- Write product requirements, workflows, user stories, acceptance criteria, and implementation plans
- Define expected user outcomes and help determine how product success should be measured
- Prioritize opportunities based on customer value, strategic importance, effort, and technical feasibility

Technical Product Collaboration

- Work closely with developers throughout product planning, implementation, testing, and launch
- Develop a practical understanding of APIs, integrations, data flows, AI capabilities, and platform constraints
- Ask effective technical questions and help teams make thoughtful product tradeoffs
- Ensure requirements are detailed enough to support efficient development without unnecessarily limiting technical solutions
- Help identify dependencies, risks, edge cases, and implementation requirements early

Product Quality and Design

- Bring strong design instincts and attention to detail to every stage of product development
- Partner with design and development teams to create clear, intuitive, and polished experiences
- Review product work carefully and identify usability issues, inconsistencies, and missing details
- Maintain a high standard for how products look, feel, and function
- Advocate for the traveler while balancing business and technical considerations

AI-Native Product Work

- Use AI tools as part of your own daily product workflow to improve speed, research, analysis, documentation, prototyping, and decision-making
- Help identify where AI can create meaningful customer or operational value
- Work with AI-enabled features, workflows, personalization systems, and data-driven products
- Evaluate when AI is appropriate and when a more structured or deterministic approach will produce a better result
- Experiment thoughtfully and help the team learn quickly from product testing and real-world use

Ownership and Execution

- Take ownership of assigned product initiatives and move them forward with limited oversight
- Keep priorities, decisions, documentation, and next steps clear
- Track progress, identify risks, and actively help resolve blockers
- Coordinate effectively across product, design, development, AI, data, and business teams
- Support testing, launches, feedback loops, and post-launch iteration
- Bring structure and momentum to a fast-moving product environment

What We’re Looking For

- Approximately three to five years of product management experience
- Experience taking digital products or features from discovery through delivery and iteration
- Experience designing and shipping consumer-facing digital products or features, not primarily enterprise software, internal tools, or B2B platforms




- Strong ability to translate ambiguous ideas into clear requirements and action plans
- Comfortable working directly with software developers and discussing technical concepts
- Familiarity with APIs, integrations, platforms, data products, developer tools, or AI-enabled products
- Extremely detail-oriented, with strong follow-through and a high standard for product quality
- Autonomous and proactive, with the ability to identify what needs to happen and move work forward
- High agency and a willingness to take responsibility for outcomes
- Strong design instincts and good judgment around usability and customer experience
- Practical experience using AI tools to improve how you work
- Strong written and verbal communication
- Comfortable working in a fully remote, collaborative, and fast-moving environment

Additional Experience That Would Be Valuable

This includes travel technology, marketplaces, booking products, or consumer travel experiences, as well as work on personalization, recommendations, search, merchandising, or customer-data products.

Background in consumer growth, retention, or engagement on B2C digital products is a plus, as is experience in a startup, scale-up, or zero-to-one product workplace. Travel industry experience is helpful but not required. Strong technical product instincts, curiosity, and the ability to learn quickly matter more.

What Success Looks Like

You'll get up to speed quickly on Traveler.md, TravelAI's existing products, and the opportunities to build current experiences on top of the platform, and from there build an effective working relationship with the Director, AI Products & Personalization and the development team. You'll bring clarity, structure, and momentum to several concurrent product initiatives, translating product ideas into detailed, actionable requirements that support efficient implementation. Success means helping launch Traveler.md integrations and new AI-powered travel products, and improving personalization experiences across TravelAI's products along the way.

Just as importantly, you'll become a trusted product partner known for autonomy, strong judgment, attention to detail, and consistently high-quality work, and you'll use AI tools effectively both to increase your own speed and to help the broader team work more intelligently.

Compensation The expected salary range for this role is C$145,000 to C$165,000 per year, depending on experience, technical depth, and overall fit.

How to Apply

Please send your résumé and LinkedIn profile to [email protected], along with a thoughtful introduction that helps us understand why this role is a strong fit for you. We prefer human written answers to an AI generated cover letter. Please send us a document answering these 3 questions. Bullet points are fine, but please use your own words.

Tell us about yourself in 5-10 bullet points.

Tell us about a project you built that you're proud of.

Why are you interested in working on Traveler.md?

We are not looking for a generic cover letter. We want to hear your perspective, understand what motivates you, and see the effort, curiosity, and product thinking you would bring to the role.

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📌 Product Manager, AI Products & Personalization (Canada)
🏢 TravelAI™, An UpNext
📍 Canada