Head of Product

2 weeks ago

Toronto, Canada Tripshepherd Full time

**About Us**

At Tripshepherd, we believe travel should be more than just an itinerary—it should be a deeply personal journey that connects travelers with the true heart and soul of each destination. As a **fast-growing startup**, we’re on a mission to create a global platform where travel creators (Tripshepherds) can share their experiences, monetize content, and build communities that benefit both locals and travelers. Our goal is to reshape tourism so that it enriches destinations, with travelers contributing positively to the places they visit, rather than simply consuming resources and leaving them worse off.

Tripshepherd is evolving into a platform where locals don’t just guide tours—they create and deliver unique, branded experiences that foster lasting, respectful relationships between locals and travelers. From exclusive guidebooks and modded maps to restaurant recommendations and community-driven content, we empower creators to tell their story and engage travelers authentically. With human-centric design and generative AI at our core, we’re building products that promote a positive, two-way relationship between locals and travelers, ensuring that tourism contributes meaningfully to local well-being, economy, and community.

We’re looking for a visionary **Head of Product** to help bring this platform to life, leading a team that will shape the future of impactful, community-driven travel.

**The Opportunity**

As Head of Product at a high-growth startup, you’ll be the architect of our travel creator platform, enabling Tripshepherds to publish, monetize, and scale their unique content in ways that benefit both travelers and locals. You will lead the integration of AI and community-building tools to create a personalized, meaningful travel experience. Imagine a platform where Tripshepherds can offer exclusive content—branded tours, insider recommendations, and unique insights—that transforms travel from sightseeing to soul-seeing, helping travelers actively contribute to the well-being of the destinations they visit.

In this pivotal role, you’ll shape how we empower travelers to make connections, build communities, and create experiences that honor both the destination and its residents—ultimately establishing Tripshepherd as the go-to platform for positive, creator-driven travel experiences.

**Key Responsibilities**
- **Vision & AI-Driven Strategy**: Lead the product strategy that integrates **generative A**I with a **community-first approach**, allowing Tripshepherds to create and monetize exclusive travel content that fosters meaningful, mutually beneficial relationships between locals and travelers.
- **Creator Empowerment**: Design and deliver tools that empower travel creators to publish, monetize, and scale their branded content responsibly. Foster community-building, enabling creators to offer guidebooks, custom maps, restaurant recommendations, and exclusive tours that positively impact local communities.
- **Connecting Locals with Travelers**: Develop features that enable local Tripshepherds to engage directly with travelers, fostering a genuine connection that enhances the traveler’s experience while supporting the well-being and economy of the destination. Ensure the platform empowers Tripshepherds to share unique cultural insights and deliver experiences that support the local economy.
- **End-to-End Product Lifecycle Management**: Own the product lifecycle, ensuring seamless integration of community-driven features, AI personalization, and content monetization capabilities.
- **Customer-Centric & Impactful Innovation**: Keep travelers and creators at the center of everything we build. Drive user research, A/B testing, and continuous iteration to enhance user experiences and promote tourism that positively impacts destinations.
- **Scalability & Community Building**: Lead the charge in developing scalable features that allow Tripshepherds to build communities, offer exclusive content, and deliver meaningful, positive travel experiences at scale.
- **Cross-Functional Collaboration**: Work closely with AI specialists, marketing, sales, and operations teams to bring products to life that blend travel with content creation, community engagement, and positive impact.
- **Data-Driven Decision Making**: Leverage data analytics to guide product development, measure success, and continuously optimize features that drive user engagement and revenue, all while promoting tourism that leaves destinations better off.

**Who You Are**
- **Visionary Leader with a Creator Mindset**: You have a passion for platforms that empower creators to own and monetize their content. You see how this can be applied to travel, enabling Tripshepherds to lead the way in impactful tourism.
- **AI & Community Advocate**: You understand the power of AI and community-driven platforms. You’re excited by the idea of integrating these into a product that brings people together while enhancing and

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