Chicago's Ocra raises $5m to accelerate AI‑led parking

Ocra, a Chicago‑based provider of parking revenue‑management software and services, has raised $5 million in strategic capital in a round led by Trestle Partners, with follow‑on participation from existing investor, hotel management company MCR. According to a company announcement, the capital is intended to accelerate product development and expand go‑to‑market efforts, particularly across the hospitality and commercial real‑estate sectors.

The company characterised the round as a milestone for a business it says reached cash‑flow breakeven while also growing “nearly 200%” year‑on‑year according to their data. The company said that their Ocra CoPilot offering, a data‑driven rate and inventory management system, has been deployed across more than 600 locations in North America, with roughly $12.3m of incremental hotel revenue generated at over 45 sites in the past six months alone.

Thomas Babcock, Partner at Trestle Partners said “Parking is no longer an afterthought, but a substantial ancillary revenue stream for asset owners. Our investment is a reflection of… the momentum that Ocra is building.”

MCR is the third‑largest hotel owner‑operator in the United States, with roughly $5.0 billion in assets under management and a portfolio of some 150 hotels.

The hotel owner was part of an oversubscribed $3.5 million round co-led by Parker Technology back in April 2024. At the time, the company then said the funds would support product development and hiring across engineering, operations and revenue functions, and the company appears to have almost doubled employee headcount since then, according to data on LinkedIn.

Alongside the funding news, Ocra announced the hire of Anthony Broad‑Crawford as Chief Technology Officer. Broad‑Crawford comes with more than two decades of experience in product roles within parking and mobility. Broad‑Crawford added that the current wave of artificial intelligence is “more significant than personal computing, the internet, and mobile computing combined.”

Beyond the capital raise and executive hire, Ocra says the fresh funds will be deployed to speed product work and expand commercial coverage — as they seek to convert early‑stage commercial traction into broader market share.