Head of Operations, Trilogy

Head of Operations, Trilogy (Remote) - $200,000/year USD Join to apply for the Head of Operations, Trilogy (Remote) - $200,000/year USD role at Crossover This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range $100.00/hr - $100.00/hr This position is designed for operators who architect and re-architect systems built to scale. Operational excellence at Trilogy is not optional—it is the competitive edge that defines us. We acquire software companies at pace and scale them even more rapidly. Sustaining this velocity requires executives capable of designing and deploying lean, automated infrastructure—not adding layers of staff to manage growing complexity. You will take ownership of comprehensive transformations spanning our global portfolio. Projects may include redesigning the offboarding process for 1,200+ employees following acquisition, replacing legacy platforms like Jira and Salesforce with AI-driven agents, or engineering automations that remove thousands of hours of manual effort. Execution will be rapid, leveraging Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of field-tested playbooks designed to keep you focused on measurable results. Trilogy manages a portfolio of 100+ products with rigorous efficiency. We function with fewer organizational tiers, shorter iteration cycles, and more demanding standards than conventional enterprise settings. This role offers the opportunity to generate impact at scale without navigating red tape or leading oversized teams. We do not operate in maintenance mode. We do not delegate transformation externally. And we do not hire individuals who require approval chains or large staffs to execute. Our focus is on a select group of deeply technical, execution-oriented leaders who treat automation as a force multiplier and velocity as a core strategy. If this describes your approach—this environment will suit you. What You Will Be Doing Driving high-complexity operational initiatives including M&A integrations, enterprise platform migrations, and large-scale organizational transitions Building and deploying automations to replace CRM and task management systems using Python and LLM APIs Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual tasks and shorten cycle times Owning initiatives end-to-end—from problem definition through deployment—applying proven playbooks and exercising executive judgment Successfully completing a technical challenge that evaluates your capability to design and deliver AI-first solutions What You Won’t Be Doing Building or managing large teams, or depending on organizational layers to achieve delivery Attending protracted alignment sessions or waiting for consensus before acting Offloading critical technical work to IT departments or third-party vendors—you will design and execute the solution directly Running steady-state operations—this role centers on transformation and speed Head Of Operations Key Responsibilities Architect and implement AI-first operational frameworks that remove manual work, reduce complexity, and enable scalable execution across Trilogy's international 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 within enterprise software 3+ years in customer-facing functions (Support, Sales, Collections, etc.) Demonstrated capability to develop automation using Python and integrate with LLM APIs Practical experience using Cursor, Windsurf, MCP, or equivalent tools to deliver production-ready automations Proven track record of moving quickly, thinking autonomously, and achieving high-stakes outcomes without supervision Nice-to-have Requirements Background leading major organizational transitions such as M&A integrations or large-scale offboarding events Track record of architecting and deploying AI-powered operational systems Collection of automations you have personally developed and deployed at scale About Trilogy Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds. Working with us 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. The payment period is weekly. Consult for more details on this topic. Crossover Job Code: LJ-5145-CA-COUNTRY-HeadofOperatio.004 Seniority level Director Employment type Full-time Job function Management, Engineering, and Strategy/Planning Industries Software Development, IT Services and IT Consulting, and Technology, Information and Internet #J-18808-Ljbffr