How Ramp Scaled Group Travel to 800+ Employees With New Tools for Large Group Bookings

When Ramp began scaling its in-person gatherings, their travel challenges quickly outgrew traditional tools. As a fast-growing fintech company with hundreds of employees traveling to the same events, Ramp needed more than discounted hotel rates. They needed a system that could handle many unique use cases without adding more overhead for their team.

Workgrounds became that system, and along the way we worked together to grow the Workgrounds platform and build new tools to help Ramp and other large teams book group travel at scale. The goal was to remove friction and unlock more value from every trip.

Ramp regularly brings large groups together for offsites, planning sessions, and team events. These trips often involve hundreds of attendees, room blocks across multiple nights, and a mix of business and personal travel plans.

Before Workgrounds, the logistical burden of these trips typically fell on a small number of people (often travel managers, executive assistants, or HR leads) who then became the central points of coordination for everything from room assignments to last-minute changes. As Ramp grew, that model became unsustainable.

1Using Product to Scale Large Group Travel

When Ramp and Workgrounds began working together, we started to see real-world use cases where new features would be of value and improve Ramp's workflows.

"We kept seeing the same blockers come up. Ramp needed more flexibility for guests without creating more work for organizers. That's where product – not process – needed to do the work."

We assessed whether the new features would be broadly beneficial to other companies and whether there would be a significant impact. Then we got to work. The result was a focused push to build features that would help companies like Ramp book travel for large groups at scale.

From initial conversations to live product, the turnaround was fast. Two of the most important features were designed, built, and launched in roughly a month so Ramp could use them for upcoming trips. Here's what we launched:

2Feature 1: Allow Guests to Claim a Room When They RSVP

One of the biggest friction points in large group travel is room assignments. Traditionally organizers had to manually assign rooms, sometimes collecting preferences through spreadsheets and emails, then reconcile everything themselves.

With the new feature we launched in October 2025, organizers can now send a single invitation to their entire group and allow guests to claim their room directly when they RSVP. This shifts room assignments from a manual, organizer-driven process to a self-serve experience for guests.

For Ramp, the impact was immediate. Hundreds of attendees could be invited at once, claim rooms on their own time, and see real-time availability – without requiring any follow-up from the organizers.

"Letting guests claim their own rooms genuinely saves our team hours on every trip, if not more. Booking our large, 800-person all company offsite would have been a nightmare without this feature."

3Feature 2: Guests Can Book and Pay for Personal Nights

We found that, like with most companies, Ramp employees often wanted to arrive early or stay late to take some personal time when traveling for work. But handling all of those one-off requests, like extending rooms, securing group rates for personal nights, and changing credit card information, was wasting way too much of the organizers' time.

So we built personal nights into Workgrounds, allowing guests to add, pay for, and manage their personal nights within the group trip, all while benefiting from the group rate. Guests can specify whether an additional night is personal or for work, pay for any personal nights on their own cards, and organizers can approve all such changes in bulk – saving hours of manual approvals and keeping guests' personal credit card information secure.

"The ability to let guests book personal nights on their own was a game-changer for us. Our team gets more flexibility, finance gets clean separation, and our organizers are no longer inundated with ad-hoc requests. We don't have to create exceptions or new processes – it just works."

4Enabling Group Travel Anywhere in the World

We also expanded the Workgrounds platform to support group hotel sourcing at any 3+ star hotel around the world. This upgrade launched earlier in the year and unlocked global inventory for room blocks and meeting spaces, which was critical for a distributed company like Ramp that hosts events all around the world.

Teams can now evaluate dozens of hotels in a single market, compare proposals, and optimize for both price and availability without additional time or cost.

5The Results: More Value from Every Trip

By removing some of the more manual processes, we helped Ramp unlock significantly more value from group travel. Now there's:

Most importantly, Ramp didn't need to build out new processes or add headcount to handle a heavy manual workload as their travel needs grew. Our platform scaled with them.

"We're building for companies like Ramp. They help us see what's missing – not just for them, but for every customer operating at that level."

6Looking Ahead

Today, Ramp uses Workgrounds across multiple trips and organizers every month, distributing travel planning without losing control or visibility. And the features originally built to support Ramp are now core parts of the Workgrounds platform, benefiting other fast-growing companies with similar needs.