Operations AI Lead

Job Overview:
This position is designed for operators who excel at creating and re-engineering scalable systems. Operational excellence at Trilogy is not optional—it's what gives us a competitive edge. We move quickly to acquire software companies and accelerate their growth even faster. To maintain this pace, we require executives capable of architecting and implementing efficient, automated systems—not those who rely on expanding headcount to handle complexity.

Duties and Responsibilities:
Delivering high-complexity operational initiatives including M&A integrations, enterprise system transitions, and organization-wide changes. Building and launching automations that supplant CRM and task management platforms through Python and LLM APIs. Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and decrease delays. Owning projects from assessment through delivery, applying established playbooks and senior-level decision-making.

Required Qualifications:
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.

Experience:
5 years

Additional Notes:
This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year.