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

This position is designed for operators capable of constructing and reconstructing systems that scale effectively.Operational excellence at Trilogy is not optional—it is a core competitive advantage. We acquire software companies rapidly and accelerate their growth even more quickly. To sustain this pace, we require executives who can architect and implement lean, automated systems rather than address complexity through additional headcount.You will oversee complete transformations spanning our global portfolio in this capacity. This might involve redesigning the offboarding process for more than 1,200 employees following acquisitions, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of manual work hours. Execution will be swift, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of proven playbooks that enable you to concentrate on results.Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This represents an opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.Steady-state operations are not our focus. Transformation is never outsourced. And we do not bring on individuals who require permission or extensive teams to produce results. We seek a select group of highly technical, execution-oriented leaders who leverage automation and treat speed as a strategic asset. If this describes you—this environment will suit you well.What You Will Be DoingDelivering high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitionsArchitecting and launching automations to replace CRM and task management platforms using Python and LLM APIsImplementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and decrease latencyDriving projects from assessment through deployment, applying proven playbooks and executive judgmentWhat You Won’t Be DoingOverseeing large teams or depending on multiple organizational layers to accomplish workParticipating in prolonged alignment sessions or waiting for consensus to proceedHanding off the complex work to IT departments or third-party vendors—you will design and implement the solution directlyRunning steady-state operations—this position centers on transformation and rapid executionHead Of Operations Key ResponsibilitiesArchitect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution throughout Trilogy's global software portfolio.Basic Requirements5+ years of operational leadership in business operationsExperience making presentations to C-suite executivesExperience writing automation in Python and integrate with LLM APIsExperience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automationsRemote work capability with at least 6 hours of overlap with the CST time zoneAbout TrilogyHundreds 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.There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!Working with usThis 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 www.crossover.com/help-and-faqs for more details on this topic.Crossover Job Code: LJ-5145-US-COUNTRY-HeadofOperatio.018