Head of Operations, Trilogy (Remote) - $200,000/year USD jobs in United States
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Crossover · 1 day ago

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

Crossover is looking for a Head of Operations to lead transformation initiatives at Trilogy, focusing on architecting systems for operational excellence. The role involves delivering high-complexity operational initiatives and implementing AI-driven automations to enhance efficiency across the company's software portfolio.

Information Technology & Services

Responsibilities

Delivering high-complexity operational initiatives including M&A integrations, enterprise system overhauls, and large-scale organizational transitions
Building and deploying automations that supplant CRM and task management platforms using Python and LLM APIs
Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and cut cycle time
Driving projects from root-cause analysis through to deployment, applying proven playbooks and executive judgment
Completing a practical technical assessment to validate your capability to architect and deliver AI-first systems
Architect and implement AI-first operational frameworks that remove manual effort, simplify complexity, and enable scalable execution across Trilogy's international software portfolio

Qualification

Operational leadershipPythonLLM APIsAutomation toolsC-suite presentations

Required

5+ years of operational leadership in business operations
Experience making presentations to C-suite executives
Experience writing automation in Python and integrate with LLM APIs
Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
Remote work capability with at least 6 hours of overlap with the CST time zone

Company

Crossover

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Crossover is a global recruitment company, founded in 2014.

Funding

Current Stage
Late Stage

Leadership Team

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Brad Weinert
COO
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Company data provided by crunchbase