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

This position is designed for systems-builders who can engineer and re-engineer operations at scale. Operational excellence at Trilogy is a strategic differentiator, not an optional pursuit. We acquire software businesses rapidly and accelerate their growth even more aggressively. Success requires executives capable of architecting lean, automated frameworks—not adding layers of management to absorb complexity. You will take ownership of comprehensive transformations spanning our international portfolio. Examples include redesigning offboarding workflows for 1,200+ employees following acquisitions, substituting Jira and Salesforce with AI-powered agents, or creating automations that remove thousands of manual work hours. Execution will be fast-paced, leveraging Python, LLM APIs, Cursor, Windsurf, MCP, and a library of battle-tested playbooks that enable you to concentrate on measurable results. Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We function with minimal hierarchy, compressed timelines, and elevated performance standards compared to conventional enterprise settings. This represents an opportunity to generate meaningful impact at scale without navigating bureaucratic obstacles or overseeing inflated teams. Steady-state operations are not part of our model. We do not delegate transformation externally. And we do not bring on individuals who require extensive approval chains or large supporting teams to produce results. Our focus is on recruiting a select group of technically proficient, execution-oriented leaders who treat automation as a force multiplier and velocity as a competitive weapon. If this describes your approach—you will excel here. What you will be doing • Driving complex operational initiatives including M&A integrations, enterprise platform migrations, and large-scale organizational restructuring • Building and deploying automations to replace CRM systems and task management platforms using Python and LLM APIs • Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce operational lag • Owning projects end-to-end from initial assessment through production deployment, applying established playbooks and senior-level decision-making • Successfully completing a practical technical assessment that validates your capacity to architect and deliver AI-centric solutions What you will NOT be doing • Building or managing large teams, or depending on hierarchical structures to achieve outcomes • Participating in prolonged coordination meetings or waiting for collective agreement to advance work • Handing off technical challenges to IT departments or third-party consultants—you will design and build solutions directly • Running business-as-usual operations—this position centers on continuous transformation and execution speed Key Responsibilities Architect and implement AI-driven operational frameworks that remove manual intervention, simplify complexity, and enable scalable execution throughout Trilogy's global software business. Candidate Requirements • Located in North America (California excluded), South/Central America, or Western Europe (UTC -8 to UTC +2) • 5+ years leading operations in enterprise software environments • 3+ years in customer-facing functions (Support, Sales, Collections, etc.) • Proven capability to develop automation using Python and integrate with LLM APIs • Hands-on experience deploying production-ready automations with Cursor, Windsurf, MCP, or equivalent tools • Established track record of operating with speed, autonomy, and consistent delivery in high-pressure scenarios Nice to have • Background leading major organizational transformations including M&A integration or large-scale employee transitions • Track record building and launching AI-based operational platforms • Documentation or examples of automations you have independently developed and deployed at scale This position is also known as: • Operations AI Lead • AI Operations Specialist • Operations AI Innovator • Head of Operations Apply tot his job