Former FLASH and Parkonect growth leader joins to scale Ocra’s hospitality industry footprint and help hotel owners and operators unlock ancillary parking revenue

 

Chicago, IL – Ocra, the first AI-powered revenue management platform purpose-built for hotel parking assets, announced the appointment of Jake Squillaci as its new Head of Sales. Squillaci will spearhead the company’s sales strategy, focusing on expanding Ocra’s footprint across parking assets in the hospitality sector.

Squillaci’s career trajectory blends deep parking industry roots with a proven track record of scaling sales at high-growth technology companies. He worked for a leading parking operator before pivoting to selling complex cloud infrastructure hardware and software, mastering the art of scaling digital-first solutions.

In 2016, anticipating a massive shift toward utilization data and online sales in the parking sector, Squillaci joined Parkonect, working alongside founder and CEO Harlan Karp. As an early employee, Squillaci was instrumental in scaling and expanding Parkonect’s full-system hardware and software solutions, successfully landing major portfolio customers and expanding the company’s footprint. Following Parkonect’s acquisition by FLASH in 2021, Squillaci served as Director of Sales for the West Coast, where he managed a $25 million budget and led a high-performing team of eight representatives.

Even with rapid technological advancements across industries, parking remains one of the last frontiers for true digital transformation – and hotel parking, in particular, is still viewed as a static guest amenity rather than a dynamic profit center. While hotels have long had dedicated revenue management technology for their core operations, Ocra has created the first actual parking revenue management controls that hotel properties need in order to maximize yield of this high-margin asset.

“We spoke with many talented sales professionals when searching for the right leader and Jake absolutely stood out,” said Ethan Glass, CEO & CoFounder, Ocra. “Jake has impressed us for years with his sales prowess and servant leader mindset. He embodies our core values, has deep domain understanding of the ecosystem, and is poised to take our highly ambitious sales team to the next level. We couldn’t be more excited to have him on board.”

“What drove me to Ocra is the tangible value we add from day one,” says Jake Squillaci, Head of Sales, Ocra. “We’re building something that fundamentally transforms how a business operates and how a hotel generates revenue. The team here is completely motivated and passionate to change the industry for the better. By optimizing parking revenue, we give hotels the financial freedom to reinvest in their properties and enhance their operations far beyond the garage. A rising tide lifts all ships, as our team always says.”

Squillaci’s hire signals momentum for Ocra expanding its footprint in the hotel sector, partnering with assets to unlock parking as a high-margin revenue stream through hands-on revenue management, sophisticated software, robust platform integrations, and AI-driven pricing strategies.

About Ocra
Ocra is the first AI-powered revenue management platform purpose-built for hotel parking assets. Hotels use Ocra to sell underutilized parking inventory to non-guest customers without adding labor or disrupting operations, increasing net operating income (NOI) while never compromising guest parking.

25+ hotel groups partner with Ocra to achieve optimum yield of their parking assets – including MCR, Starwood Capital Group, Aimbridge, Stonebridge, Highwood Properties, Concord Hospitality, and OTH Hotels & Resorts. Ocra has raised $10M in strategic funding to date – $3.5M in an oversubscribed round in April 2024 led by MCR and Parker Technology, and $5M led by Trestle Partners with significant follow-on from MCR in August 2025.

Ocra was named the winner of the 2026 ALIS Tech Challenge and was ranked #1 overall on Hotel Tech Report’s Global Best Parking Management software list in the 2026 HotelTechAwards.

For more information, visit getocra.com or email info@getocra.com.

Media Contact:
Sarah Becherer
SVP, Marketing
Ocra
sarah@getocra.com