Not accepting applications on crossover.com at this time.
There's a fundamental inefficiency in the SaaS world: operations traditionally don't scale. A typical VP of SaaS Operations oversees 1-3 products with headcount that grows linearly—add more products, add more people. Trilogy is demonstrating a different model. We're acquiring one SaaS company monthly and running 47+ products (expanding toward 100+) with team growth that's sublinear, proving that operations scale through 80-90% automation rather than proportional hiring.
This isn't routine operational maintenance. You'll drive the operational execution that supports 12 acquisitions annually. This is neither a corporate IT position nor an infrastructure management function. This is a hands-on leadership opportunity for someone who has built and owned SaaS Operations at a SaaS organization, not merely contributed as a team member. The right candidate combines technical depth with leadership capability, someone energized by designing operational frameworks that scale, embedding automation, and navigating high-impact operational decisions. You'll own the evolution of SaaS Ops across a varied portfolio of SaaS businesses, guaranteeing smooth product integrations and leveraging AI to build an automated, exceptionally efficient operations engine.
You'll collaborate with world-class colleagues spanning Engineering, Product, and C-Suite leadership to develop and deliver this vision. If you hold firm convictions about how SaaS Operations should function, relish the complexity of optimizing multi-product ecosystems, and want to pioneer AI-driven operations, this role is for you.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.






It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.