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Transforming Multi-Day Travel with AI: Why We’re Excited to Lead WeTravel’s Series C

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Transforming Multi-Day Travel with AI: Why We’re Excited to Lead WeTravel’s Series C

Behind curated multi-day trips like a yoga retreat, cycling adventure across the Pyrenees or a tour through Italy, there’s often a business juggling a web of moving parts. Travelers paying on different timelines, multiple vendors to coordinate and pay, foreign exchange conversions, contracts to manage and itineraries to finalize. Unlike other areas of travel, these operators frequently rely on fragmented tools and manual workflows that make growth difficult to achieve at scale.

WeTravel was built to change that. From our very first conversation with WeTravel CEO Ted Clements and the team, we felt it was clear that they’re on a mission to transform the complex world of multi-day travel, streamlining the digital experience for operators of all sizes. That’s why we couldn’t be more excited to lead WeTravel’s $92M Series C round.

We’ve seen how vertical software can transform entire industries through companies like EliseAI, Supio, Project44, Side and others, evolving into end-to-end platforms that fundamentally simplify business operations. We believe WeTravel is on that trajectory, and are thrilled to be part of the journey ahead as the company expands globally, launching new platform capabilities to power the future of multi-day travellers.

Complexity in Group Travel That Doesn’t Scale

Ask any multi-day travel operator–it’s not just about crafting an itinerary. It’s about managing countless moving parts, such as collecting payments from travelers across borders, paying vendors in multiple currencies, handling legal waivers and keeping every traveler informed along the way.

The reality is most organizers still run their businesses on spreadsheets, email chains and a patchwork of point solutions that don’t talk to each other. The result is a ‘Frankenstein’ configuration for payins, payouts and administrative workflows that add complexity, drive up costs and prevent travel operators from focusing on what is most important: creating delightful travel experiences and growing their businesses.

Overview of Multi-Day Travel Business Payments & Operational Workflows 

The diagram below illustrates just how many stakeholders, workflows and financial touchpoints operators must navigate. Travel buyers sit on one side, vendors on the other and in the middle is the operator—stuck managing everything from payments and approvals to marketing, CRM and itinerary building–often without the right technology in place.

Operating System Purpose-Built for Multi-Day Travel

WeTravel is a one of a kind platform purpose-built for the unique needs of multi-day group travel. In the last few years, the product has evolved from a core payments and booking engine, into an all-in-one operating system where organizers can seamlessly collect payments in multiple currencies with flexible installment options, manage participant details through a branded portal and reconcile finances in real time. WeTravel also offers capabilities for creating and sharing mobile-friendly itineraries powered by AI, issuing virtual or physical cards for on-the-road expenses and simplifying every aspect of trip planning and execution.

WeTravel Evolution: From Payments & Booking Engine to Full Operating System

The top of the chart below illustrates the ‘status quo’ fragmentation of the booking, payments, and administrative workflows for multi-day travel operators. They rely on a patchwork of tools for sales, marketing, client engagement, contracts, spreadsheets and payment platforms to manage suppliers. WeTravel consolidates all of these activities onto a central platform, powering not only booking & payments, but also all of the relevant upstream sales and downstream functions so operators can manage the entire workflow seamlessly.

Much like how Visa provides the rails for global commerce, WeTravel is becoming a backbone of a very unique and fragmented ecosystem in travel, bridging the gaps between travelers, operators and vendors, and streamlining the payments and workflows that connect them. With this new funding, WeTravel will double down on AI to power both growth and efficiency for organizers. Intelligent tools like itinerary builders, contract management and automated operations will leverage AI to replace manual work. At the same time, the supplier network will expand into a true marketplace where organizers and vendors can seamlessly discover, contract and transact. Together, these initiatives position WeTravel to become a holistic, connective network for multi-day travel.

Demonstrating CEO-Market Fit with Relentless Execution

Ted Clements_headshot

Ted Clements, CEO, WeTravel

We’re big believers in CEO-market fit and in our opinion, no one fits this framework better than WeTravel’s CEO, Ted Clements. Ted brings deep experience in the travel sector, including his time as the COO of FareHarbor where he helped scale the company to several hundred millions in revenue through its acquisition by Booking.com

From closing deals to calling the shots, Ted’s career in travel technology has given him a rare perspective on this sector. His rise from sales rep to COO during his time at FareHarbor proves that he has both the hustle and know-how to take a travel platform to new heights. 

It’s clear from each interaction with Ted and the WeTravel team, they know how to move quickly, iterate on customer feedback and maintain a break-neck pace of innovation. From launching AI-powered itinerary builders to expanding into new financial services like card issuing, WeTravel is relentlessly focused on shipping products that help their travel operator businesses thrive.

At Sapphire Ventures, we love partnering with companies building essential infrastructure behind big, fragmented markets. The multi-day group travel industry, despite its size and cultural significance, has long lacked a modern operating system. WeTravel is giving travel organizers the tools to manage complex trips with confidence, while unlocking more revenue opportunities and ultimately empowering entrepreneurs to build thriving businesses in one of life’s most joyful industries.

If you want to learn more about what WeTravel is up to or explore open roles, you can check it out here.

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