How Block Saved $150,000 Per Trip and Went From Zero to Booked in 48 Hours with Workgrounds

Block, the parent company of Square, Cash App, and Tidal, has hubs all over the US and frequently gathers to bring together their remote-first teams. Traditionally, this kind of travel planning can stretch into weeks: figuring out where to host the meeting, RFPing hotels one by one, then working through a slow contract negotiation for the room block. But Block values flexibility in its travel and wanted a solution that allowed for short planning timelines and on-demand booking.

Workgrounds helped Block keep its flexible approach to trips and secure group rates as a rule. What used to take weeks to source, days to contract, and constant manual upkeep to manage, now happens in as little as 48 hours from search to signed room block, with guests handling much of their own logistics after that. Block has used the platform for several trips, consistently securing group rates 30% below standard pricing. Here's how.

1Planning without the lead time

When Aimee Wong of Block's Executive Operations team started planning her first event on Workgrounds – a 150-person gathering for the Controllership team – she didn't have a destination in mind. Block has hubs across California and in cities like Atlanta, London, and New York City, so there's never a default answer for where to gather the distributed team.

Done manually, that decision alone can take weeks. Comparing markets and properties against headcount, dates, budget, and available amenities means hours of research on tools built for one-off, self-serve trips. Then you have to send RFPs, track responses, and compare bids yourself. Most planning teams end up defaulting to one city and a handful of properties just to keep the search manageable, with no real way to know if that choice is the most economical.

Aimee used Workgrounds' hotel sourcing tools alongside the Flight Estimator tool to evaluate all of Block's hub cities at once, automating RFPs to roughly 75 hotels across six potential markets. The bids came back in less than 48 hours.

"I expected to be sourcing hotels for weeks. Instead I basically clicked through the search, focused on other work, and came back to bids from all the hotels in a few days."

The data pointed to Atlanta as the clear winner on rate, hotel availability, and travel logistics. This decision took two days instead of the weeks it would normally take to compare six markets by hand. That kind of turnaround matters most for a distributed team like Block's, where the next team's offsite can't always wait for a month of lead time.

2Booking without endless contracts

Booking a hotel for an individual or a small group is easy: search, find the rate that fits, select your rooms, check out. It's a simple e-commerce transaction. But once you cross the 9-room threshold, you fall into an entirely different process. Room blocks typically require a negotiated contract, which means legal and finance reviews, redlines, and back-and-forth that can take days or weeks.

Shannon Middlebrooks, another Executive Operations partner at Block, had no room for that kind of timeline. She needed a San Francisco hotel contracted and booked for a trip just three days before check-in – not enough time for a traditional room block negotiation.

Workgrounds handled the contract negotiation in the background, working within the terms and conditions of Block's existing master services agreement (MSA), saving Shannon from having to negotiate or deal with the contract process. Instead of every booking triggering a new contract and extended legal review, the MSA already covers the legal groundwork, and the contract for any specific booking is generated straight from those terms.

"I'd normally be chasing legal and the hotel for a week just to get a contract signed. This felt as fast as booking my own vacation, not a 150-person block."

Three days after picking the hotel, guests were arriving. That's one of the reasons why Block chose Workgrounds: Whether it's a three-day timeline, a first-time planner, a team of one – none of it requires the time or expertise room block negotiations used to demand. Booking 100 rooms now takes the same effort as booking one.

3Managing without the manual work

With a simple CSV upload, Aimee added the full 150-person guest list for Atlanta into Workgrounds, where each guest could log in via their Okta single sign-on without needing a separate account or invite. From there, guests could claim their rooms, adjust their check-in and check-out dates, or add on personal nights before or after the offsite (on their personal credit cards, while still getting the group rate).

Across the Atlanta and San Francisco trips, 15% of guests changed their dates or added on personal nights. When even the simplest guest changes can mean a lot of back-and-forth on the organizer's end, that's hours of admin work saved that Aimee and Shannon could use to focus on much more critical event functions.

"I didn't realize how much time I was losing to guest management until I got that time back."

4The results

With Workgrounds, Block has cut the lead time it takes to choose a market, the back-and-forth it takes to get a hotel under contract, and the manual work it takes to manage guest bookings, all without giving up the group rates and legal protections that room blocks are meant to secure in the first place.

When Block's People team booked its event in San Francisco for 40 people, it was run by a different organizer who had never used Workgrounds before, but the hotel sourcing tools, effortless contracting, and self-serve guest management didn't require extensive onboarding or training. It's a small preview of what happens when Workgrounds rolls out company-wide: Every team gets to take advantage of group rates, without anyone having to learn the ins and outs of travel planning and hotel contract negotiations.

That consistency shows up in the numbers, too. Across its portfolio of trips with Workgrounds, Block has booked travel in well under a week each time and consistently secured 30% off the hotel costs, saving an estimated $300,000 in total. For a team that needs to move quickly and stay flexible, speed and savings aren't the exception anymore – they're now the standard Block expects from every gathering.