Director of Operational Excellence, Trilogy (Remote)

This position is designed for operators who specialize in building and restructuring systems that achieve scale.

Operational excellence at Trilogy is not optional—it is the foundation of our competitive advantage. Our model is built on acquiring software companies rapidly and scaling them with even greater speed. To sustain this pace, we require executives capable of engineering lean, automated systems rather than addressing complexity through workforce expansion.

You will assume ownership of comprehensive transformations spanning our global portfolio. This may involve redesigning offboarding processes for over 1,200 employees following acquisitions, substituting Jira and Salesforce with AI-driven agents, or constructing automations that remove thousands of manual hours. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a repository of validated playbooks that enable you to concentrate on results.

Trilogy operates a portfolio exceeding 100 products with uncompromising efficiency. We function with reduced organizational layers, accelerated cycles, and elevated performance standards compared to conventional enterprise settings. This is an opportunity to generate impact at scale without confronting bureaucratic obstacles or overseeing inflated teams.

We do not engage in steady-state operations. We do not delegate transformation externally. And we do not recruit individuals who require authorization or extensive teams to produce results. Our search is for a select group of deeply technical, execution-oriented leaders who leverage automation for advantage and velocity for strategy. If this describes you—this environment will suit you exceptionally well.

What You Will Be Doing

• Delivering high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Engineering and launching automations that replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual tasks and decrease latency
• Driving initiatives from diagnosis through deployment, applying proven playbooks and executive-level decision-making
• Executing a hands-on technical assessment to validate your capacity to design and deliver AI-first solutions

What You Won’t Be Doing

• Overseeing large teams or depending on multiple layers of personnel to achieve outcomes
• Participating in prolonged alignment sessions or requiring consensus to advance
• Assigning the complex work to IT or external vendors—you will architect and execute the solution directly
• Sustaining steady-state operations—this position is centered on transformation and speed

Director Of Operational Excellence Key Responsibilities Engineer and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.

Basic Requirements

• 5+ years of operational leadership in business operations
• Experience delivering presentations to C-suite executives
• Experience developing automation in Python and integrating with LLM APIs
• Experience utilizing Cursor, Windsurf, MCP, or similar tools to deliver production-grade automations
• Remote work capability with at least 6 hours of overlap with the 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-GB-London-DirectorofOper.001