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There's an unspoken truth in the SaaS world: operational scalability remains elusive. A conventional VP of SaaS Operations typically oversees 1-3 products, with team size growing in lockstep with product count. Trilogy is demonstrating a fundamentally different approach. Acquiring one SaaS company monthly, we now operate 47+ products—scaling toward 100+—while maintaining sublinear headcount expansion through 80-90% automation rather than proportional hiring.
This position transcends routine operational maintenance. You'll drive the operational execution that supports 12 annual acquisitions. This is neither a corporate IT position nor an infrastructure oversight role. This is a hands-on leadership opportunity for someone who has personally built and owned SaaS Operations at a SaaS organization—not merely contributed as a team member. The ideal candidate combines technical mastery with leadership capability, thriving on architecting scalable operational systems, embedding automation, and navigating high-impact operational decisions. You'll define the evolution of SaaS Operations across a varied portfolio of SaaS enterprises, guaranteeing frictionless product integration and leveraging AI to construct an automated, exceptionally efficient operations engine.
You'll collaborate with elite peers spanning Engineering, Product, and Executive leadership to architect and implement this vision. If you hold strong convictions about how SaaS Operations should function, relish the complexity of optimizing multi-product ecosystems, and are energized by pioneering AI-enabled operations, this role is your opportunity.
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.