Operations AI Lead

$200,000 USD/year ^{Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks}  ($100 USD/hour)

This role breaks the traditional VP mold. You will not inherit a reporting team, attend recurring status syncs, or prepare quarterly strategy presentations. There is no existing operation to manage at steady state.

Instead, you will lead M&A diligence and integration efforts for enterprise software acquisitions, take ownership of P&L goals for distinct business units, deploy AI-powered automations using cutting-edge tooling, negotiate agreements with vendors, and deliver findings directly to portfolio CEOs, CFOs, and functional leadership. All of this work is yours to execute—simultaneously, across multiple portfolio entities.

Trilogy specializes in acquiring and revitalizing distressed enterprise software businesses, targeting a cadence of one deal every week. Our 10-person VP of Operations group oversees operational execution for more than 50 portfolio companies. The scope divides into three core areas: full-cycle acquisitions (from due diligence through integration), serving as effective COO for business units (managing budgets, P&L, vendor ecosystems), and advising central functions (Support, SaaS, Engineering) to align their initiatives with measurable business impact.

This is a high-exposure, high-consequence position where daily priorities shift constantly. You will shape decisions made by key stakeholders throughout the organization—portfolio CEOs, functional heads, and deal execution partners. Success here demands initiative: you develop your own conviction, marshal the data, and drive stakeholders to action without waiting for alignment.