Whoop wants to nearly double the size of its Boston headquarters, according to a lease the fitness-tracker maker is pursuing for 107,000 square feet of office space in a building right next door to its current home at One Kenmore Square near Fenway Park. The additional space would be enough to accommodate roughly 1,000 more employees, a dramatic bet on growth as the company inches toward a public offering.
The planned expansion, first reported by Bloomberg, has not yet been finalized, and the lease has not been signed. Whoop already occupies all eight floors of Related Beal's Commonwealth Building at One Kenmore Square, a 121,000-square-foot headquarters it first signed onto in 2021, according to Bisnow. Bloomberg's Greg Ryan reports that CEO Will Ahmed believes in the local talent pool as a reason to keep growing in the city rather than looking elsewhere, even as the report notes Boston is struggling to grab a bigger piece of the artificial intelligence boom.
A War Chest to Match the Ambition
The expansion push comes just months after Whoop closed a $575 million Series G funding round in March that pushed its valuation to $10.1 billion, according to a Whoop press release. That round was led by Collaborative Fund, with participation from the Qatar Investment Authority, Mubadala Investment Company, Abbott, and Mayo Clinic. It marked a nearly threefold jump from Whoop's $3.6 billion valuation during its August 2021 Series F round, which was led by SoftBank's Vision Fund 2, per Sacra.
The company's underlying business has scaled quickly. Whoop reported reaching roughly 2.5 million active members while its annual bookings doubled year-over-year in 2025 to surpass $1 billion, according to Hoodline's earlier reporting on the funding round. Whoop is the maker of screenless fitness trackers that have become popular among athletes and everyday consumers alike, monitoring metrics like sleep, recovery, and strain.
Eyeing an IPO Within 18 Months
Ahmed said in August that Whoop remains on track for an initial public offering in roughly 18 months, according to Athletech News. The company was founded in 2012 by Harvard University alumni Ahmed, John Capodilupo, and Aurelian Nicolae, launching out of the Harvard Innovation Lab before growing into one of Boston's most closely watched homegrown tech companies, per Built In Boston.
Whoop has also leaned heavily into artificial intelligence as a growth engine. In September 2023, the company partnered with OpenAI to launch WHOOP Coach, becoming one of the first wearable makers to integrate GPT-4 directly into its app for personalized biometric recommendations, according to OpenAI. That AI push has since made Whoop's Kenmore Square offices something of a stage for state government, too — in February, Massachusetts Governor Maura Healey hosted a press announcement at the headquarters unveiling a state contract that deploys an OpenAI ChatGPT assistant to roughly 40,000 executive branch workers, as Hoodline reported at the time.
A Neighborhood in Transition
The proposed expansion would land Whoop in the middle of a Kenmore Square that is already being reshaped. The company's headquarters sits directly next to the iconic Boston CITGO sign at 660 Beacon Street, which went dark in May for a six-month project to raise it 30 feet and shift it 120 feet east, a transformation Hoodline covered in its reporting on the sign relocation.
The timing also lines up with a broader recovery in Boston's downtown office market. The market recorded 803,879 square feet of positive net absorption in the second quarter of 2026, with overall vacancy dropping to 18.7%, according to CBRE data cited by the Boston Real Estate Times. A 107,000-square-foot commitment from a single tenant would rank among the city's largest office leases of the year, a sign that major occupiers are once again willing to expand their footprints downtown.
Whether Whoop can pull off the hiring surge that a doubled headquarters implies remains an open question. The company would need to build out a pipeline for up to 1,000 new employees in a competitive AI talent market, all while keeping its IPO timeline intact amid uncertain public market conditions heading into late 2027 or early 2028.
