Head of Operations, Trilogy; Remote

This position is designed for operators capable of constructing and reconstructing systems rational excellence at Trilogy represents our competitive edge, not an optional priority. Our model involves rapid software company acquisitions followed by even faster scaling. Sustaining this momentum requires executives who can architect and implement lean, automated systems—without relying on increased headcount to manage complexity. You will take ownership of comprehensive transformations spanning our global portfolio.

This may include redesigning the offboarding process for 1,200+ employees following an acquisition, substituting Jira and Salesforce with AI agent solutions, or creating 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 suite of established playbooks that allow you to concentrate on results. Trilogy operates a portfolio of 100+ products with disciplined efficiency.

We function with reduced hierarchies, accelerated cycles, and elevated standards compared to conventional enterprise settings. This represents an opportunity to generate significant impact at scale without navigating bureaucratic obstacles or overseeing oversized teams. Steady‑state operations are not part of our model. We internalize transformation rather than outsource it. We do not recruit individuals who require approval or extensive teams to execute.

Our search is for a select group of highly technical, execution‑oriented leaders who leverage automation and treat speed as strategic doctrine. If this describes you—this environment will suit you well.

• Executing operationally complex projects including M&A integrations, enterprise system transitions, and large‑scale organizational restructuring
• Architecting and delivering 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 initiatives end‑to‑end from problem identification to production deployment, applying established playbooks and executive judgment
• Completing a practical technical assessment to validate your capability to design and execute AI‑first solutions

• Overseeing large teams or depending on organizational layers to accomplish objectives
• Participating in prolonged alignment sessions or waiting for consensus before taking action
• Handing off the complex work to IT departments or third‑party vendors—you will design and implement the solution directly
• Running steady‑state operations—this position is centered on transformation and rapid execution

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

• 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

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.

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 ‑and‑faqs for more details on this topic.

Crossover Job Code: LJ-5145-US-Atlanta-Headof Operatio.
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