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Crossover · 1 day ago

Head of Operations, Trilogy (Remote) - $200,000/year USD

United States

Full-time

Remote

Lead/Staff, Director/Executive

$200K/yr - $200K/yr

5+ years exp

Crossover is a company that specializes in acquiring and scaling software companies. They are seeking a Head of Operations who will be responsible for architecting and implementing AI-first operational systems to enhance efficiency and drive transformation across their global portfolio.

Information Technology & Services

Responsibilities

Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions

Building and launching automations that replace CRM and task management platforms using Python and LLM APIs

Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual processes and cut latency

Owning initiatives end-to-end—from analysis to go-live—leveraging established playbooks and executive-level decision-making

Completing a practical technical assessment to showcase your capability to architect and deliver AI-first solutions

Architect and implement AI-first operational systems that remove manual work, reduce complexity, and enable scalable execution across Trilogy's global software portfolio