Director of Operational Excellence, Trilogy (Remote) - $200,000/year USD

This position is designed for operational leaders who design and rebuild systems to achieve scale. Operational excellence at Trilogy is not optional—it is a strategic advantage. We acquire software companies rapidly and scale them faster still. Sustaining this pace requires executives capable of creating lean, automated systems—not adding layers of management overhead. You will take full ownership of transformations spanning our global portfolio. This may involve re-engineering the offboarding process for 1,200+ employees following an acquisition, replacing legacy platforms like Jira and Salesforce with AI-driven agents, or deploying automations that remove thousands of hours of manual effort. You will move quickly using Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep you focused on delivery. Trilogy manages a portfolio of 100+ products with disciplined efficiency. We maintain fewer organizational layers, shorter execution cycles, and higher performance standards than conventional enterprise settings. This role offers the opportunity to generate meaningful impact at scale, free from bureaucratic friction or the need to oversee large teams. We do not engage in steady-state operations. Transformation is never outsourced. And we do not hire individuals who require approval or large teams to achieve results. We seek a select group of technically proficient, execution-driven leaders who treat automation as leverage and velocity as competitive strategy. If this describes your approach—this environment will suit you. What You Will Be Doing Leading high-complexity operational initiatives including M&A integration, enterprise system transitions, and large-scale organizational restructuringBuilding and deploying automations using Python and LLM APIs to replace CRM platforms and task management systemsImplementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and accelerate executionOwning projects from initial analysis through full deployment, applying proven frameworks and exercising executive-level judgmentCompleting a technical assessment designed to validate your capability to architect and deliver AI-first operational solutions What You Won’t Be Doing Building or managing large teams or depending on organizational hierarchy to drive outcomesAttending prolonged coordination meetings or waiting for consensus before taking actionHanding off critical technical work to IT departments or third-party consultants—you will design and execute the solution directlyRunning steady-state operations—this role centers on transformation and speed Director Of Operational Excellence Key Responsibilities Architect and implement AI-first operational systems that remove manual tasks, reduce complexity, and enable scalable execution across Trilogy's global portfolio of software companies. Basic Requirements Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)5+ years leading operational initiatives in enterprise software environments3+ years in customer-facing functions (Support, Sales, Collections, etc.)Proven capability to write automation scripts in Python and integrate with LLM APIsHands-on experience deploying production-grade automations using tools such as Cursor, Windsurf, MCP, or equivalentTrack record of moving quickly, thinking independently, and delivering high-impact results with minimal oversight Nice-to-have Requirements Background leading complex organizational transitions including M&A integrations or large-scale employee offboardingPrior experience designing and deploying AI-powered operational platformsA portfolio of automations you have personally designed 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. 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-DE-COUNTRY-DirectorofOper.001