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

This position is for operators capable of designing and redesigning systems at scale. Operational excellence at Trilogy is not optional—it's a core competitive advantage. We move quickly to acquire software companies and scale them even more quickly. Sustaining that pace requires executives who can architect lean, automated infrastructure—not add layers of management to handle complexity. You'll take ownership of complete operational transformations spanning our global portfolio. This might include redesigning the offboarding process for 1,200+ employees following an acquisition, replacing platforms like Jira and Salesforce with AI-driven agents, or creating automations that remove thousands of hours of manual effort. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of proven frameworks that keep you focused on results. Trilogy manages a portfolio of 100+ products with disciplined efficiency. We work with fewer hierarchies, shorter cycles, and greater accountability than conventional enterprise settings. This is an opportunity to create meaningful impact at scale without navigating red tape or overseeing large, unwieldy teams. We do not run steady-state operations. We do not delegate transformation to third parties. And we do not hire leaders who require consensus or extensive support structures to deliver. We are building a small cadre of highly technical, execution-oriented leaders who treat automation as a force multiplier and speed as a strategic asset. If that describes you—this environment will suit you well. What You Will Be Doing

Executing operationally complex initiatives including M&A integration, enterprise platform migration, and large-scale organizational restructuring Architecting and delivering automations that replace CRM and task management systems using Python and LLM APIs Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and accelerate execution Driving projects end-to-end—from diagnosis through deployment—using established playbooks and senior-level decision-making Completing a technical assessment to validate your ability to design and build AI-first operational solutions What You Won’t Be Doing

Building or managing large teams or depending on multiple organizational layers to execute Spending time in protracted alignment sessions or waiting for group consensus to proceed Handing off the technical heavy lifting to IT departments or third-party vendors—you will design and implement the solution directly Running business-as-usual operations—this role centers on transformation and rapid execution Head Of Operations Key Responsibilities

Architect and implement AI-first operational infrastructure that removes manual overhead, reduces complexity, and enables scalable execution across Trilogy's worldwide software portfolio. Basic Requirements

5+ years of operational leadership in business operations Experience presenting to C-suite executives Experience building automation using Python and integrating with LLM APIs Experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable platforms Ability to work remotely with a minimum of 6 hours overlap with CST time zone 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. 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 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 www.crossover.com/help-and-faqs for more details on this topic. Crossover Job Code: LJ-5145-CA-Vancouve-HeadofOperatio.003

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