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

This position is designed for operators capable of constructing and reconstructing scalable systems. Operational excellence at Trilogy is not optional—it is a competitive advantage. Our acquisition pace is aggressive, and our scaling velocity is even sharper. To sustain this momentum, we require executives who can architect lean, automated systems rather than absorb complexity through expanded headcount. You will take ownership of complete transformations spanning our global portfolio. This may involve redesigning the offboarding process for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI-driven agents, or constructing automations that remove thousands of manual hours from operations. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of validated playbooks that enable you to prioritize results. Trilogy operates a portfolio exceeding 100 products with disciplined efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This represents an opportunity to generate impact at scale without navigating bureaucracy or overseeing inflated teams. We do not engage in steady-state operations. Transformation is not outsourced. We do not recruit individuals who require approval or large teams to produce results. Our search is for a limited number of deeply technical, execution-oriented leaders who leverage automation and treat speed as strategic doctrine. If this describes you—this environment will suit you. What You Will Be Doing

• Driving high-complexity operational projects including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Architecting and delivering automations that displace CRM and task management platforms using Python and LLM APIs
• Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual effort and compress cycle times
• Owning initiatives from assessment to implementation, applying proven playbooks and executive-level decision-making
• Successfully completing a technical challenge that validates your capability to design and deploy AI-first solutions

What You Won’t Be Doing

• Overseeing large teams or depending on organizational layers to execute work
• Participating in prolonged alignment sessions or waiting for consensus before taking action
• Handing off difficult work to IT departments or third-party vendors—you will design and implement the solution directly
• Supporting steady-state operations—this role centers on transformation and rapid execution

Director Of Operational Excellence Key Responsibilities Architect and implement AI-first operational systems that remove manual tasks, reduce complexity, and enable scalable execution throughout Trilogy's global software portfolio. Basic Requirements

• 5+ years of operational leadership in business operations
• Experience delivering presentations to C-suite executives
• Experience building automation in Python and integrating with LLM APIs
• Experience deploying production-grade automations using Cursor, Windsurf, MCP, or similar tools
• 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-US-Atlanta-DirectorofOper.008 Apply tot his job Apply To this Job