Extraordinary experiences for good

IfOnly is an online marketplace to buy and sell extraordinary, one-of-a kind experiences. 

Challenge

Design a trusted marketplace that could scale from a concierge-supported service into a self-sustaining ecosystem without losing the quality and emotional connection that made the experiences valuable.

Solutions

1. Mobilize

To meet the needs of aspiring on-the-go luminaries, mobile tools were essential. Evangelizing responsive design throughout the company helped us optimize the site for mobile use. I also defined and launched IfOnly's first iOS and Android apps.

2. Provide structured communication 

To ensure IfOnly marketplace luminaries fulfill experiences that exceed expectations with minimal supervision, I defined a structured communication system. To automate communication between IfOnly and luminaries, I defined a simple To-Do List that sends notifications when fulfillment tasks must be complete. Each task needed to complete a booked experience- from confirming schedules and locations, to creating and sending beautiful, personalized itineraries for each guest- was distilled and built into the system. To improve communication between customers, luminaries and IfOnly, I designed a secure omni-channel messaging system that allows for the company to be alerted to requests that have gone unanswered in case IfOnly Concierge needed to step in to close the communication loop.

3. Enable plans to change

Customers and luminaries need to modify orders post-purchase, so I defined an order modification system that allows luminaries and customers to request and negotiate changes to booked experiences. Granted requests that deal with schedule or duration automatically update the availability calendar. Granted requests that require payment such as additional guests, increased duration or add-ons automatically charge the customer. 

4. Facilitate discovery of a growing marketplace

As the IfOnly marketplace grew, we needed to provide an experience to help our customers discover new experience categories at different price points across multiple cities. User research taught us that grouping inventory into Interests, Activities & Occasions, and Destinations encouraged serendipitous discovery and increased conversion.

Outcome

The vendor workflow system launched, including tools for marketplace fulfillment, on-boarding, order management, customer service, and payouts, enabled the company to successfully manage a 300%+ annual growth rate in orders.

Reception

Reflection

IfOnly’s marketplace demonstrated how product design can connect storytelling, commerce, and social impact. By designing for both buyers and sellers who want to give back to their community, we created a platform that balanced usability, trust, and emotional engagement while supporting long-term growth (IfOnly was acquired by MasterCard Priceless Cities). Building cross-functional teams to deliver high-quality end-to-end experiences optimized to balance customer delight with operational feasibility for sellers was key to the platform’s success. It was a personal pleasure to contribute to a system that connects social impact with commercial success, and a fun challenge to scale marketplace platforms with complex workflows.

Emerging Technology Context

We built a platform that combined philanthropic e-commerce, social discovery, and mobile-first experiences to connect users with curated, once-in-a-lifetime experiences. The technology was emerging in its integration of marketplace dynamics, mobile usability, and social engagement—a first-of-its-kind platform, linking philanthropy and commerce. Marketplace success depended less on transaction efficiency than on reducing uncertainty. By treating operational workflows, communication systems, and service recovery as integral parts of the customer experience, we were able to increase trust while enabling the platform to scale operationally.

What I’d Do Differently Now

The biggest lesson wasn’t about marketplace mechanics. It was that extraordinary experiences depend on trust between strangers. Every workflow, notification, and communication tool was ultimately about reducing uncertainty while preserving the sense of anticipation and delight that made the experience feel special.

Today, I would invest in tools that help customers understand and improve their contributions to their local communities, leveraging data-informed storytelling to highlight impact and drive repeat engagement. I would further strengthen the platform’s capability to support ongoing relationships between customers and sellers, extending beyond one-time transactions.