Rippling, the San Francisco-based human resources software company backed by $1.8 billion in venture capital, is nearing a lease for nearly 30,000 square feet of office space at 111 South Wacker Drive in downtown Chicago. If finalized, the deal would give the workforce management platform its first physical foothold in the city, with plans to bring on a manager role tied to a future Chicago office as soon as early next year.
The pending agreement, first reported by The Real Deal, comes per Crain's Chicago Business, though the deal terms remain undisclosed. A Rippling spokesperson declined to comment on the pending lease, and Union Investment, the German company that owns and serves as landlord of 111 South Wacker Drive, has not detailed the arrangement publicly. Rippling currently lists 19 job openings based in Chicago, an early signal of the buildout to come if the lease closes.
A Trophy Tower Built for a Post-Law-Firm Era
111 South Wacker Drive is a 51-story blue-glass tower built in 2005 and designed by Lohan Caprile Goettsch Architects, offering 1.2 million square feet in the heart of the Loop. The building sits at 92 percent leased, according to CoStar Group, a mark that towers well above the downtown Chicago office market's 72 percent average leasing rate — a gap that underscores the flight-to-quality trend reshaping the city's commercial real estate landscape.
That resilience hasn't come without turnover. Deloitte, still the building's anchor tenant, renewed a 330,000-square-foot lease in 2015 before later trimming its footprint by roughly 200,000 square feet, according to The Real Deal. Law firms Locke Lord and White & Case both departed the tower two years before publication of the Rippling report. Union Investment has worked to backfill that space, including a lease signed with law firm Venable, while pursuing tech tenants to round out its roster.
Rippling's Rapid Rise Since Its 2017 Founding
Rippling was founded in 2017 and now generates more than $1 billion in annualized revenue, according to the pending lease report. CEO Parker Conrad has said the company employs 5,000 people globally. Rippling's platform automates payroll, benefits, hiring and other workforce management tasks for employers, a compound-product approach that Conrad built after his earlier venture, HR software startup Zenefits, according to Entrepreneur. The company's scale was cemented in April 2024, when it raised $200 million in Series F funding led by Coatue, pushing its valuation to $13.5 billion, per PYMNTS.com.
Joining a Wave of Bay Area Tech Names in the Loop
Rippling would not be the only West Coast tech name making a move on downtown Chicago this year. Stripe and Databricks have each inked or are finalizing downtown Chicago deals, and blockchain firm Ripple has done the same, all per Crain's Chicago Business reporting cited in the lease report. Databricks entered lease negotiations in May for a large block of space at The Franklin tower on West Monroe Street, as Hoodline previously reported, while Ripple signed for space at 300 North LaSalle Street in River North back in April.
The pattern reflects a broader split in Chicago's office market. Cushman & Wakefield data from mid-2026 showed overall Central Business District vacancy at 27.2 percent, but vacancy in trophy-class buildings sitting at just 13.4 percent — a divide Hoodline detailed in coverage of a $213 million refinancing tied to the same flight-to-quality trend. Suburban Chicago office space, by contrast, hit a record-high 33.4 percent vacancy in the first quarter of 2026, fueling a wave of building surrenders and data center conversions across the metro area.
Union Investment's tower has effectively become a case study in how premier, amenity-rich buildings are absorbing space vacated by shrinking law firms and downsizing anchor tenants, repositioning it toward fast-growing tech and fintech occupiers instead. Whether Rippling's Chicago team ultimately grows beyond its initial footprint, or how quickly the company's global workforce integrates the new office, remains to be seen once the lease terms are finalized.
