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 represents our competitive edge. Our business model centers on rapid software company acquisitions followed by even faster scaling. Sustaining this pace requires executives who design and implement lean, automated infrastructure rather than addressing complexity through expanded headcount.

You will take ownership of comprehensive transformations spanning our international portfolio. Projects may include restructuring the offboarding process for over 1,200 employees following acquisition, substituting Jira and Salesforce with AI‑driven agents, or creating automations that remove thousands of manual work hours. Execution will be rapid, leveraging Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of validated playbooks that allow you to concentrate on results.

Trilogy operates a portfolio exceeding 100 products with uncompromising efficiency. Our structure features fewer hierarchical levels, accelerated execution cycles, and elevated performance standards compared to conventional enterprise settings. This represents an opportunity to generate large‑scale impact without navigating bureaucratic obstacles or overseeing inflated teams.

We do not engage in steady‑state operations. Transformation is not outsourced. We do not recruit individuals requiring approval or substantial teams to deliver results. Our search targets a select group of deeply technical, execution‑oriented leaders who leverage automation and employ speed as strategic advantage. If this describes your approach—you will excel here.

What You Will Be Doing

• Delivering complex operational initiatives including M&A integrations, enterprise system transitions, and large‑scale organizational changes
• Building and launching automations that supplant CRM and task management platforms through Python and LLM APIs
• Implementing AI‑enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and decrease response time
• Driving projects from initial assessment through full deployment, applying established playbooks and executive‑caliber decision‑making
• Finishing a practical technical assessment to validate your capability to architect and execute AI‑centric solutions

What You Won’t Be Doing

• Overseeing large teams or depending on multiple organizational layers to accomplish objectives
• Participating in prolonged alignment sessions or waiting for consensus to proceed
• Assigning the challenging technical work to IT departments or third‑party vendors—you will design and implement solutions directly
• Supporting steady‑state operations—this position focuses on transformation and rapid execution

Director Of Operational Excellence Key Responsibilities

Architect and implement AI‑centric operational infrastructure that removes manual effort, reduces complexity, and enables scalable execution throughout Trilogy's worldwide software portfolio.

Basic Requirements

• 5+ years of operational leadership in business operations
• Experience making presentations to C‑suite executives
• Experience writing automation in Python and integrating with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to ship 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 for more details on this topic.

Crossover Job Code: LJ-5145-IT-COUNTRY-DirectorofOper.002

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