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

This position is built for operational leaders who engineer and re-engineer systems designed to scale.

Operational excellence at Trilogy is not optional—it is our competitive edge. We acquire software businesses rapidly and scale them with even greater speed. Sustaining this pace requires executives capable of designing and deploying lean, automated systems—not adding layers of management to absorb complexity.

You will take full ownership of transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 1,200 employees following an acquisition, replacing legacy platforms like Jira and Salesforce with AI-driven agents, or creating automations that remove thousands of hours of manual effort. Execution will be rapid, using Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that allow you to prioritize results.

Trilogy operates a portfolio of more than 100 products with disciplined efficiency. We maintain fewer organizational layers, shorter decision cycles, and higher performance standards than conventional enterprise settings. This is an opportunity to generate meaningful impact at scale without navigating bureaucracy or overseeing inflated teams.

We do not focus on steady-state operations. We do not outsource strategic transformation. And we do not hire leaders who require extensive teams or approval chains to deliver outcomes. We are seeking a select group of deeply technical, execution-oriented leaders who leverage automation for impact and treat speed as a strategic asset. If that describes you—this environment will suit you well.

What You Will Be Doing

• Leading operationally complex initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Building and deploying automations that replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
• Driving projects from diagnostic phase through deployment, applying proven playbooks and executive-level decision-making
• Completing a practical technical challenge that demonstrates your capability to design and deliver AI-first solutions

What You Won’t Be Doing

• Building or managing large teams or depending on multiple organizational layers to achieve results
• Participating in prolonged alignment sessions or waiting for consensus before taking action
• Handing off technical work to IT departments or third-party vendors—you will design and implement solutions directly
• Running steady-state operations—this role centers on transformation and rapid execution

Head Of Operations Key Responsibilities Architect 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 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

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-HeadofOperatio.017