Empower Anyone to Create Amazing Travel Experiences
SquadTrip is the group travel booking platform that makes it easy to plan, promote, and collect payments for group trips.
Growing Fast, Building for the Future
Trusted by organizers across the country to manage group travel payments.
Backed by investors and recognized by TechCrunch, PhocusWire, AP News, and Skift.
There's a better way ↓Our Founders
SquadTrip was founded by Darrien Watson and Stevon Judd, avid travelers and passionate entrepreneurs who saw firsthand how difficult it was to organize group trips. They set out to build the platform they wished existed — one that handles the logistics so organizers can focus on the experience.
Darrien Watson
Co-Founder & CEO
Darrien leads product and strategy at SquadTrip, driven by a passion for making group travel accessible to everyone. Before founding SquadTrip, Darrien organized dozens of group trips and experienced the headaches of chasing payments, managing spreadsheets, and juggling group chat threads. That frustration became the spark for SquadTrip. He brings a deep understanding of what organizers need because he has been one himself. Darrien is focused on building a product that saves organizers time and gives them confidence that every detail is handled.
Stevon Judd
Co-Founder & CTO
Stevon leads engineering at SquadTrip, building the technology that powers thousands of group trips. With a background in software development and a love for travel, Stevon saw the opportunity to apply modern technology to a space that had been overlooked. He architects the systems behind automated payment plans, real-time dashboards, and seamless Stripe integrations. Stevon is committed to building a reliable, scalable platform that organizers can trust with their most important trips.
Our Story
SquadTrip started the way a lot of great companies start — with a real problem that the founders could not ignore. Darrien and Stevon were planning their own group trips and kept running into the same wall. There was no single tool designed for the job. Instead, they were cobbling together spreadsheets to track who had paid, sending Venmo requests that went unanswered, and drowning in group chat threads trying to coordinate logistics.
Every trip was the same cycle: excitement at the start, followed by weeks of chasing people for money and fielding endless questions about dates, prices, and room assignments. The organizer always bore the burden, and the tools available were never built for group travel. They were general-purpose apps awkwardly repurposed for a very specific and complex use case.
Darrien and Stevon knew there had to be a better way. So they built it. SquadTrip was born out of that firsthand frustration — a platform purpose-built for group travel organizers, where everything from creating a booking page to collecting payments to sending reminders lives in one place. No more spreadsheets. No more chasing payments. No more guesswork.
What started as a solution to their own problem quickly resonated with thousands of other organizers who were dealing with the exact same pain points. Today, SquadTrip serves more than 2,000 organizers and 50,000 travelers, and the team continues to build features that make group travel simpler, more transparent, and more enjoyable for everyone involved.
Our Values
These are the principles that guide everything we build and every decision we make at SquadTrip.
Simplicity
We remove complexity so organizers can focus on what matters — the trip itself. Every feature we build is designed to reduce steps, eliminate confusion, and make group travel management feel effortless. If it does not make things simpler, we do not ship it.
Empowerment
We give organizers superpowers. Whether you are a first-time planner coordinating a friends trip or a professional travel advisor managing dozens of groups, SquadTrip gives you the tools to operate like a pro. We believe anyone should be able to create amazing travel experiences, regardless of experience level.
Trust
Trust is the foundation of group travel. Travelers trust organizers with their money and their plans. We earn that trust through transparent pricing with no hidden fees, secure payment processing via Stripe, and clear communication tools that keep everyone on the same page.
Community
We celebrate group travel culture. Travel is better together, and we are building more than a platform — we are building a community of organizers who share a passion for bringing people together through travel. We support, learn from, and grow alongside the people who use SquadTrip every day.
Built to Handle the Heavy Lifting
Our mission is to streamline group trip planning and execution. Whether you are organizing a destination wedding, a retreat, or a large-scale group tour, SquadTrip gives you the tools to create booking pages, automate payment plans, communicate with travelers, and track everything in real time.
Our Philosophy
“Travel brings people together.”
We believe that shared travel experiences create bonds that last a lifetime. SquadTrip exists to remove the friction from group travel so more people can experience the world together.
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Start organizing your next group trip with SquadTrip today.