Case study: Flagship customer conference
Client: Expensify
Event Type: Flagship customer and partner conference
Locations: Puglia, Italy, Bora Bora, and Maui
Dates: 2023, 2018, and 2016
Attendees: 100 top accounting professionals + guests
The challenge
Expensify wanted to deepen relationships with its most influential customers, partners, and leading accounting professionals worldwide through a bespoke, invite-only conference retreat. The goal was to foster community, surface product insights, and boost brand loyalty in an immersive, distraction-free environment.
ExpensiCon 3 — Italy, 2023
Strategy & execution
We crafted a highly curated, multi-touch experience:
Exclusive invite‑only community: Limited to 100 high-impact accounting leaders plus the option to bring a +1, amplifying connection both professionally and personally.
Multi-month nurturing process: Participants began engaging upon receiving invites, ensuring pre-event KPIs were met and to generate excitement and anticipation.
Five-day conference in Puglia: Hosted at the luxurious Borgo Egnazia resort, blending conference, not-so-typical “networking” events, and Italian culture.
Immersive local experiences: Included a convoy of 100 classic Italian cars winding through olive groves to a castle for sunset cocktails and a gala, as well as small group excursions to deepen partner-to-partner relationships.
High-caliber content: Featured power sessions with celebrity and industry speakers—like George Clooney—alongside Expensify’s leadership and roadmap workshops.
No sponsors, exhibitors, or ads: Purely community-first programming, emphasizing authentic connection and value.
Highlights
Community building: A tight-knit group sharing insights, challenges, and successes created a safe space for candid discussion.
Guest invitation: "+1s" fostered emotional bonds and enriched the personal experience.
Seamless execution: All logistics—from curated journeys to lodging and event flow—were purposefully orchestrated to delight and engage.
Results & impact
Cultivated a meaningful peer network among accounting leaders, enhancing product advocacy and community loyalty.
Gained strategic customer insights, directly influencing Expensify’s product roadmap.
Elevated Expensify’s brand by delivering a world-class, award-worthy client event.
Increased partner revenue targets and refreshed strategic co-initiatives with all accounting firms that attended.
Services delivered
Pre-event community engagement & invitation strategy
Full “retreat” venue design, production, and logistics coordination
Bespoke brand moments that showcased the local culture: convoy excursions, curated meals, gala, and cultural tours
High-profile speaker management and content planning
Conference agenda planning — speaker management, presentation practice, and content development
Guest +1 experience support to maximize emotional connection
Post-event impact capture and roadmap alignment
“Imposter Syndrome… is often defined as someone feeling like they don’t deserve to be in a certain position or space. Well, Simon certainly felt that way for both #ExpensiCon 2 and for 3. We were surrounded by giants in the accounting and fintech industry from across the globe. We experienced hospitality reserved for celebrities and even had one visit us (George Clooney). To all fellow attendees we had the privilege to meet and connect with, it was awesome and can’t wait to continue the journey beyond the trip.”
ExpensiCon 2 — Bora Bora, 2018
Location: Bora Bora, French Polynesia
Focus: Partner relationship building, client growth, and brand building
This second installment emphasized continued partner relationship building, client growth, and brand building. By fostering deeper strategic partnerships, we set the stage for firm growth, future co-marketing, and integrated growth.
Key responsibilities:
Oversaw creative strategy, budget, brand voice, event messaging, and a team of 5 who helped execute the event.
Collaborated with partnerships and sales teams to ensure high-touch partner engagement.
Developed frameworks to track revenue impact and long-term partner value.
Developed the agenda, and worked with speakers to develop their presentations.
Results & impact
Gathered critical product feedback to grow our accounting channel.
Opened new monetization pathways with top partnerships.
Created life-long evangelists within the accounting thought leadership community.
“There are moments in life when our experience completely transcends our expectations - ExpensiCon II has been one of those occasions.”
ExpensiCon 1 — Hawaii, 2016
Location: Maui
Focus: Influencer engagement & market validation
The inaugural event was a bold experiment: bring together the most influential voices in finance, let the brand speak through experience, generate buzz in the accounting community, and sign key contracts with Top 100 accounting firms. It worked.
Key Responsibilities:
Co-led strategic planning, budget allocation, and event production.
Partnered with sales and partnerships to curate a high-impact attendee list, goals for each partner, and hit those target goals.
Crafted positioning and narratives to drive long-term product alignment and advocacy.
Built the monetization model for future ExpensiCon playbooks.
Impact:
Validated the event model that would shape Expensify’s future GTM strategy.
Cultivated early champions who helped scale brand reach organically through partner content.
Created the foundation for a repeatable, high-ROI experiential strategy.
Signed 50% of the top 100 accounting firms within a year post-event
Strategically deepened the Expensify community network (including introducing a few to their future employers).
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