Head of Operations, Trilogy (Remote) - $200,000/year USD

Job Description:

This position is designed for operators capable of designing and redesigning systems built to scale.

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Operational excellence at Trilogy is not optional—it is our competitive edge. We move quickly to acquire software companies and scale them even more rapidly. Sustaining this pace requires executives who can architect lean, automated systems rather than relying on headcount to absorb complexity.

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You will take ownership of complete operational transformations spanning our global portfolio. Examples include restructuring the offboarding process for 1,200+ employees following acquisitions, replacing platforms like Jira and Salesforce with AI-driven agents, or deploying automations that remove thousands of hours of manual effort. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that allow you to concentrate on results.

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Trilogy operates a portfolio of 100+ products with disciplined efficiency. We maintain fewer organizational layers, shorter cycle times, and more demanding standards than conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or managing oversized teams.

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Steady-state operations are not part of our model. We do not outsource transformation. We do not hire individuals who require extensive permission structures or large teams to deliver results. We are seeking a limited number of highly technical, execution-focused leaders who treat automation as leverage and speed as core strategy. If this describes you—this environment will suit you well.

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What You Will Be Doing

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• Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Building and deploying automations to replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and shorten execution cycles
• Owning initiatives end-to-end—from diagnosis through deployment—applying proven playbooks and executive-level decision-making
• Completing a practical technical assessment to validate your capability to architect and deliver AI-first solutions

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What You Won’t Be Doing

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• Building or managing large teams or depending on multiple reporting layers to achieve outcomes
• Participating in prolonged alignment sessions or waiting for consensus before taking action
• Handing off complex work to IT departments or third-party vendors—you will design and execute the solution directly
• Operating in a steady-state maintenance capacity—this role centers on transformation and speed

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Head Of Operations Key Responsibilities

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Architect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.

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Basic Requirements

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• 5+ years of operational leadership in business operations
• Experience making presentations to C-suite executives
• Experience writing automation in Python and integrate 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

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About Trilogy

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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.

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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!

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Working with us

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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.

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Crossover Job Code: LJ-5145-US-Atlanta-HeadofOperatio.019