This role is designed for operators who own outcomes — not advisory roles, not reporting functions, but full accountability for delivering multi-million-dollar results. You will lead high-stakes operational initiatives across a global software portfolio, converting complexity into measurable financial performance. You will design the programs, execute the strategy, and witness your contributions reflected directly in margin expansion, retention rates, and acquisition integration success.
Trilogy manages a broad, diversified portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant unrealized financial potential. Your responsibility will be to lead the transformations that unlock that potential. From driving a $2M/quarter renewal uplift program to reducing cloud infrastructure costs without sacrificing performance, or integrating a newly acquired company into the Trilogy operating model in 30 days — your contributions will be tracked at the executive level. You will shape profitability across multiple business units.
This position suits candidates who perform best in high-visibility, high-autonomy settings. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, structure decision-making, and execute faster than conventional operating teams. Hierarchy and bureaucracy will not constrain you; instead, you will have the latitude — and the responsibility — to generate clarity, secure alignment, and act with conviction. If you find energy in converting intricate operational challenges into reliable, scalable wins, you belong here. Apply if you are prepared to lead transformational initiatives that redefine how an entire software portfolio operates.
Architect and execute portfolio-wide transformation initiatives that produce measurable improvements in retention, cloud cost efficiency, and acquisition integration — with direct executive exposure and tangible impact.
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.
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