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Ocra — Unlimited PTO Jobs

The parking revenue-management platform runs remote-first with a flexible work-from-anywhere policy and unlimited PTO.

5 day weekUnlimited PTOChicago, United StatesMedium (51-200)Fully Remote

About Ocra

What is Ocra?

Ocra is the revenue-management layer for parking: software that helps parking operators, hotels and asset owners distribute their inventory across the aggregators consumers actually book on (SpotHero, ParkWhiz and the rest), manage rates dynamically, and reconcile the revenue — the airline-style yield toolkit an overlooked, cash-heavy industry never had. Founded in 2018 and backed by ~$11M, Chicago-based Ocra works with major operators and a growing hotel-parking business, selling calm, measurable revenue lift in an industry still run on spreadsheets. The market timing is good: parking is consolidating fast around aggregator demand, and operators who can't manage channel inventory dynamically leave real money on the table — Ocra sells the fix to an industry that measures results in occupancy points, so the feedback loop from feature to customer revenue is short and visible.

Where will I work?

From wherever suits you: Ocra's adverts describe a "Flexible work-from-anywhere policy" and a "remote-first environment", with Chicago as the home base rather than a mandate — current roles list as remote or Chicago-optional.

What is the Ocra team like?

Around 50 people across engineering, product, sales and operations — small enough that a full-stack engineer or an account executive sees their work land with named customers within weeks. An honest double note: Ocra is young enough to have no review-site footprint (the similarly named Glassdoor entities belong to other companies — we checked), and its time-off phrase appears in three of seven current adverts spanning two functions — the minimum spread our verification standard accepts; both facts are disclosed here rather than hidden. Current openings span an account executive seat and product/engineering roles including a technical product owner — a compact slate where each hire visibly changes the roadmap.

Work-Life Balance

The policy line, verbatim: "Unlimited PTO that supports work-life balance" — alongside comprehensive health cover and a work-from-anywhere setup.

Perks and Benefits

  • "Unlimited PTO that supports work-life balance" — verbatim, Sales + Engineering adverts
  • "Flexible work-from-anywhere policy" in a "remote-first environment"
  • "Comprehensive benefits: medical, dental, & vision"
  • "Company-sponsored 401k"
  • Early-stage ownership in a category-defining vertical platform
  • Chicago base, optional

Open Positions

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No open positions

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