The Challenge

Travelers don’t trust generic OTA listings. Reviews are anonymous, itineraries are vague, and there’s little accountability once the booking is done. Younger travelers, especially Gen Z, have shifted their discovery to TikTok and Instagram, but those platforms don’t connect to bookable experiences.

Hosts need better tools to scale trust. They can’t just rely on a profile picture and a line of text. They need structured ways to show what their experiences are, who they are, and why travelers should trust them.

Our job was to build a system where trust and discovery were inseparable , not bolted on after the fact.

My Role

I led product and design across the MVP, working with squads distributed across Canada, Pakistan, and Brazil. My role wasn’t just to design flows or prioritize a backlog, it was to create the systems and frameworks that allowed the team to move quickly, stay aligned, and build something coherent.

• Product Strategy: Sequenced the roadmap into three themed sprints (social → discovery → booking).
• Design Leadership: Directed app navigation, feed design, booking flows, and review functionality.
• Cross-functional Orchestration: Aligned engineers, designers, and ops across three continents.
• Org Practices: Transitioned teams from Jira to Plane and restructured epics, stories, and tasks to fit hybrid squads.

The Approach

We worked in arcs, each sprint layering onto the last:

1. Videos & Profiles: gave us the social foundation, TikTok-style feed, profile pages, engagement.
2. Search & Navigation: built discovery flows, filters, and search.
3. Booking & Post-Tours: tied it together with trust: reviews, cancellation flows, refund clarity.

The sequencing mattered. We didn’t start with booking because trust isn’t something you bolt on. It has to grow out of the way people discover, engage, and connect.

Solution Pillars

1. Trust & Transparency

• Rich experience pages with itineraries, host profiles, and transparent pricing.
• Video & text reviews for accountability.
• Cancellation flows with clear refund breakdowns.

2. Quality Content & Discovery

• TikTok-style video feed with city, experience, and following filters.
• Social tagging, location metadata, and 'See More' deep links to experiences.

3. Scalable IA & Booking

• Global search with filters for city, date, price, and accessibility.
• Experiences hub with tabs for all, booked, and saved.
• Booking confirmation with shareable link, guest management, and refund policies.

4. Operational Foundations

• BOAT moderation tool extended to TripShepherd for content, users, and experiences.
• Analytics framework spanning growth, sales, and engagement.

Reviews as the Keystone

Reviews became the growth loop, more than just feedback:

• Guests gain trust from authentic video and text reviews.
• Hosts build reputation and credibility.
• Platform collects structured data for better recommendations.
• Content from reviews feeds back into discovery.

Growth

Acquisition Through Deep-Linking Our Network

Thanks to the incredible work of our sales and partnership teams and our MVP, we were able to onboard a significant network of content creators and experience creators. By providing deep linking to our network's profiles and experiences, we created a kind of symbiotic relationship between TripShepherd's goals and our creator network's.

As creators shared their profiles and experiences for increased reach and revenue, we gained a free acquisition channel.

Low-Friction Exploration and Onboarding

While this isn't anything novel, TripShepherd's combination of travel and social commerce platforms is. Social commerce, in general, is still fairly novel in the Western world. This meant we had to allow low-friction exploration and onboarding to help users understand the platform. Sign-up prompts only show up when a user wants to perform an action which is tied to a user account. For example, saving an experience. If they've attempted to save an experience, we've already activated them.

Onboarding

Another complication with this novel combination of platforms meant we had to implement patterns in a novel way. Some onboarding gave some guidance, but we also didn't want to front-load information, so we provided behaviour-specific onboarding when a user performed a relevant action. A little bit of help when needed.

Retention and Engagement Through Shared Profits

TripShepherd is a B2B2C app at its core. We're helping experience creators book their experience, and content creators build their audience. In this context, the work of the latter is advertising for the former. So we created a profit-sharing feature. If a user books an experience through a content creator's video, the content creator gets a cut.

Of course, this creates massive retention benefits and encourages content creators to push engagement on their content from their other networks.

But we also allowed regular users to post their content after completing an experience, so why not allow them the same profit-sharing? This gives us an army of users, content creators, and experience creators pushing their friends, audiences, and customers who get paid if their content is engaged with.

Results

Tripshepherd now hosts hundreds of experiences across Niagara Falls, Toront, and New York City, with content posted from users around the Americas.

Our onboarding features helped us onboard 1000s of users in the first few months, after seeing some pretty dismal retention rates due to the novelty of the platform.

Our retention and engagement features have also led to the Creator Marketplace, currently in closed beta. This allows content creators and experience creators to partner with each other, helping experience creators grow their audience and content creators grow their income.