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Built by someone who spent 20 years
making fragmented markets legible.

Benny Rachamim
Founder & CEO

Owl & Odds was founded by Benny Rachamim, a 20 year enterprise software operator: a decade at Eloqua through its Oracle acquisition, sales leadership at Infor, scaling Uberflip's revenue organization through acquisition, co founding Freight Hero, and currently leading global sales at a16z backed Supermove.

The pattern across that career: underserved markets that needed a data and intelligence layer. Freight. Logistics. And now the largest one yet: 45 million American bettors with no honest tooling, served by an industry that profits from keeping it that way.

The company began with a test that disproved its own easiest marketing pitch, and chose to publish the result. That choice is the company. We believe the first honest actor in a dishonest category does not just win customers. It defines the category.

Owl & Odds is headquartered in Ontario, Canada, and operates to iGaming Ontario standards.

benny@owlandodds.com
Founder & CEO, Owl & Odds
The career

Twenty years inside markets
that needed a legibility layer.

2006–12
Eloqua · AE to DirectorThrough the category that became marketing automation.
2012–18
Oracle · Director to Sr. DirectorFollowing the Eloqua acquisition into the enterprise.
2016–18
Infor · VP Sales, North AmericaEnterprise vertical software at scale.
2018–22
Uberflip · SVP RevenueScaled the revenue organization through acquisition.
2022–24
Freight Hero · Co FounderBuilt go to market from zero in logistics technology.
2024–now
Supermove · VP Global Salesa16z backed. The same thesis, the next market.

Responsible use & disclaimer

Owl & Odds is an analytics and entertainment product, not betting advice. We never accept wagers. Must be 19+ in Ontario or of legal age in your jurisdiction. Past signal performance does not guarantee future results. If gambling stops being entertainment, help is available: ConnexOntario 1 866 531 2600. Owl & Odds operates to iGaming Ontario / AGCO standards.