Head of Operations, Trilogy

Head of Operations, Trilogy (Remote) Compensation: $100 USD per hour ($200,000 per year). Full-time, 40 hours per week, 50 weeks per year. Contractor of Record via Crossover. Payment weekly. This role requires an operations leader capable of rapidly building and restructuring systems that scale. Operational excellence is core to Trilogy’s competitive advantage. We acquire software businesses quickly and accelerate their growth; this pace demands executives who architect lean, automated systems rather than expanding personnel. What You Will Be Doing Executing operationally complex projects including M&A integrations, enterprise system migrations, and large-scale organizational transitions. Architecting and delivering automations that replace CRM and task management platforms using Python and large‑language‑model APIs. Implementing AI‑powered workflows through Cursor, Windsurf, and MCP to eliminate manual processes and reduce cycle time. Driving initiatives from problem diagnosis to deployment, applying proven playbooks and executive‑level decision‑making. Completing a hands‑on technical assessment to validate your ability to design and deploy AI‑first solutions. What You Won’t Be Doing Building or managing large teams or relying on hierarchical structures for execution. Participating in prolonged alignment sessions or waiting for consensus to proceed. Handing off complex technical work to IT departments or external contractors; you will design and implement solutions directly. Operating in maintenance mode—this role focuses on transformation and speed of execution. Head Of Operations Key Responsibilities Architect and implement AI‑first operational systems that remove manual effort, reduce complexity, and enable scalable execution across Trilogy’s global software portfolio. Basic Requirements Located in North America (excluding California), South/Central America, or Western Europe (UTC –8 to UTC +2). 5+ years of operational leadership in enterprise software. 3+ years in customer‑facing roles (Support, Sales, Collections, etc.). Demonstrated ability to write automation in Python and integrate with LLM APIs. Experience using Cursor, Windsurf, MCP, or similar tools to ship production‑grade automations. Proven ability to move fast, think independently, and deliver high‑stakes results without handholding. Nice‑to‑haves Experience leading large‑scale organizational transitions such as M&A integrations or mass offboarding. History of designing and deploying AI‑driven operational systems. Portfolio of automations you have personally built and shipped at scale. About Trilogy Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our focus is simple customer‑facing designs. We incubate new ideas and rearchitect existing projects for the modern cloud‑based stack. Trilogy offers a collaborative environment where you can grow your career by leaps and bounds. Working With Us This is a full‑time (40 hours per week), long‑term position. The role is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. Compensation is $100 USD per hour ($200,000 USD per year assuming 40 hours per week and 50 weeks per year). Payment is weekly. For more information, consult Crossover FAQs. Seniority Level Director Employment Type Full‑time Job Functions Management, Engineering, and Strategy/Planning Industries Software Development, IT Services and IT Consulting, and Technology, Information and Internet Referrals increase your chances of interviewing at Crossover by 2x. #J-18808-Ljbffr