Outside wanted to expand into the travel industry and explore the potential of how AI could improve the product as well as accelerate discovery and development.
After acquiring Inntopia, Outside needed to unlock near-term value from the platform while also defining a net-new travel product aligned with its brand. Through workshop-driven discovery and AI-assisted synthesis, this work aligned leadership on a human-first, AI-assisted travel direction—securing funding and a dedicated team to take the concept forward.
Exploring Travel as a New Growth Vector
Outside wanted to expand into the travel market following the acquisition of Inntopia, a SaaS booking and inventory platform. The ambition was twofold: unlock immediate value from the acquisition, while also identifying what a net-new Outside travel product could be.
This work ran in parallel with a broader directive to explore how AI could accelerate product discovery and development.
- Put Inntopia’s backend and inventory to work as quickly as possible.
- Define a longer-term travel product opportunity aligned with Outside’s brand and audience.
Workshop-Driven Discovery and Alignment
The workstream was structured around a series of workshops that I designed and facilitated for a cross-functional group of leaders from product, design, engineering, and business.
The initial workshops focused on understanding Inntopia—what it enabled today, where it fell short, and how it might fit into Outside’s ecosystem. This created a shared baseline and surfaced early constraints.
A key near-term insight was that Inntopia’s out-of-the-box experience was not sufficient for direct use within Outside products. However, there was strong alignment that rebuilding the front end on top of the existing backend would unlock meaningful value quickly.
Near-Term Execution Through Principles, Not Mockups
From the first workshop, we generated a clear set of requirements for a reimagined front-end experience. Because this initiative explicitly aimed to trial AI-assisted workflows, engineers were embedded directly in the sessions.
Rather than producing traditional mockups, I defined a set of guiding principles and interaction constraints. Engineers began building immediately, using these principles as direction. I then provided iterative feedback on early implementations, refining the experience collaboratively.
This approach significantly reduced handoff friction and allowed us to test a faster, more fluid design–engineering loop.
Defining the Long-Term Product Direction
While many longer-term ideas existed, there was no alignment on which opportunity to pursue. A second workshop focused on evaluating concepts through the lens of user value and Outside’s differentiation, allowing us to converge on a general direction.
A third workshop then explored that concept in more depth, identifying unknowns, risks, and areas requiring further discovery.
Following alignment, I used AI tools to accelerate synthesis—first summarizing workshop outputs, then generating a structured PRD. This allowed me to produce a working prototype within hours of the final session.
While intentionally rough, the prototype helped validate direction with stakeholders and highlighted where deeper thinking was still required.
Human-First, AI-Assisted Travel
The aligned concept centered on travel itineraries. In parallel with using AI to speed up the process, there was a clear mandate to use AI thoughtfully within the product itself.
Outside is built on human-created content, so the challenge was balancing automation with curation. I developed a product vision that positioned AI as an assistant—augmenting human expertise rather than replacing it.
Impact
I presented this vision to leadership and the CEO, securing approval, funding, and a dedicated team to take the work forward.
- Launched the first Outside travel OTA
- Identified a new product opportunity in the travel market.
- Created alignment across stakeholders and executive leadership.
- Established and validated AI-assisted discovery and delivery processes.
