This position is designed for operators who take full ownership of multi-million-dollar financial outcomes — not those who observe, advise, or simply track. You will assume direct control of the most critical operational initiatives across a global software portfolio, converting uncertainty into concrete, measurable financial performance. You will design the programs, lead the execution, and witness your contributions reflected in margin expansion, retention metrics, and acquisition integration results.
Trilogy operates a broad and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and substantial untapped financial opportunity. You will spearhead the transformations necessary to unlock that value. Whether you are executing a $2M quarterly renewal uplift program, reducing cloud expenditure without compromising system performance, or integrating a newly acquired company into the Trilogy operating model within 30 days, your contributions will be clearly visible to executive leadership. Your work will directly shape profitability across dozens of 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 accelerate analytical work, structure strategic insights, and drive outcomes more rapidly than conventional operating teams. You will not be constrained by rigid hierarchy or bureaucratic process; you will have both the latitude — and the mandate — to establish clarity, secure cross-functional alignment, and execute with conviction. If you are motivated by transforming complex operational challenges into scalable, repeatable successes, you will thrive in this environment. Apply if you are prepared to lead transformative initiatives that redefine how an entire software portfolio operates.
Design and execute portfolio-wide transformation programs that deliver measurable improvements in retention, cloud efficiency, and acquisition integration — with executive-level visibility and direct financial 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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