Executive Assistants are the connective tissue of any organization: managing calendars, coordinating between teams and partners, keeping leadership running smoothly, and generally serving as the keepers of institutional knowledge and culture. In high-growth tech environments especially, where the pace is relentless and the teams are distributed, EAs are usually the ones quietly holding everything together.
Case in point: At Calm, the Executive Assistant team plans company travel and gatherings in addition to dozens of other ownership roles. Previously they used a third-party agency as support to source hotels and book room blocks, but it just couldn't keep up with Calm's always-on tempo of high frequency smaller trips.
When the EA team decided to look for a new solution, they worried that cutting out the agency would mean absorbing all the logistical burden themselves. Instead they chose Workgrounds' AI-enabled platform, which took on the logistical grind and gave the EAs back their most valuable resource: time. Time that they used to focus on shaping experiences, strengthening culture, and making every gathering feel intentional.
1The Challenge: High-Frequency Travel Breaks the Agency Model
Agencies work by routing client needs through a network of contractors who manually hunt for the right hotel fit. It's a model built in a different era, and it has trouble stretching to the always-on travel programs that remote-first companies now run as a matter of course.
Lisa Breiman, Executive Assistant to the CEO, Co-Founders, and President at Calm, puts it plainly:
"At the pace we move, we needed something we could just pick up and run with. When we worked with an agency for travel, we were always one step removed from the process, and that made it hard to move fast or get creative."
One of the other options – taking the work in-house and manually sourcing room blocks – would have had major operational costs. It takes companies 100 emails on average to coordinate the RFP process and secure a hotel. Multiply that by the annual travel portfolio for a company like Calm (30 bids, in four markets, across 20 trips), and the number of emails grows exponentially. And that's just to secure the hotel contract. For a lean team already juggling dozens of other priorities, that overhead just did not compute.
2The Solution: Speed & Visibility Unlock Intentional Planning
Calm's team of Executive Assistants needed to move faster and book more group travel without taking on more work. They found that solution in Workgrounds. From first demo to signed contract, the EA team onboarded the platform entirely on their own with zero IT or procurement hiccups.
"The whole thing just worked. We were running RFPs on our own within the first week, and nobody had to hold our hand. That's not something you expect from an enterprise platform."
The starting point is the RFP generator; it asks for the same information the EAs would typically give an agency, but with more controls and zero room for missing details or misinterpretation. The new AI search functionality even lets you enter your search in natural language, looking for things like "artsy boutique hotels in Nashville for 20" or "hotels for 40 with a courtyard in the Garden District of New Orleans."
From there, AI agents run in the background to surface the full landscape of bids. Each hotel room block option shows total cost transparency and clearly identifies matching or missing criteria. Plus, the team can easily play with trip parameters to re-run RFPs and see how the results change.
While the automated RFP process is the biggest win, Workgrounds' suite of additional trip planning tools has become indispensable for Calm. A built-in Flight Estimator shows where attendees are coming from and surfaces the most cost-effective destinations. This has opened up a whole tier of markets that wouldn't have made it off the map previously. In fact, that's how some of the team's favorite gatherings happened in places like Philly and the Twin Cities.
Once a destination is booked, organizers can customize the trip splash page with invite information, agendas, and trip details for each attendee. This gives the team full control over the narrative of every gathering while dramatically cutting down on inbound questions. And while any planner will tell you that trip logistics really start to spiral when individuals want to make changes after booking, the Calm team can fine-tune individual stays with a couple of clicks – or simply hand it off to guests to manage themselves.
"When we planned our annual Sales Kickoff this year – 42 rooms in Newport Beach – Workgrounds helped us research hotels and book the full room block while essentially customizing each guest's stay. It gave us so much control with zero headaches."
3The Result: From Logistics Team to Culture Architects
"We're seeing more EA teams driving travel programs at remote-first companies, and that makes a lot of sense," says Nikhil Sethi, CEO of Workgrounds. "They bring a level of care and cultural understanding that you just can't outsource. Our job is to give them a tool that keeps up."
For Calm's EA team, that's exactly what happened. What started as a search for a faster way to book hotels became something bigger: the infrastructure for an always-on travel program built around culture, not logistics. The old process of coordinating every trip manually through an agency and contractors has been replaced by something the team can pick up and run with the moment a need arises. And it's helped them host 130 guests across 265 room nights in just one year of travel.
But the most meaningful change is what the EA team does with the space Workgrounds created. They can pulse-check markets, explore destinations, and run RFPs as frequently as they want. They can build splash pages and agendas that make every trip feel intentional. They've recentered Calm's gathering program on culture rather than logistics – and that's exactly what Workgrounds was built to do.
