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

This position is designed for operators capable of building and rebuilding scalable systems from the ground up. Operational excellence at Trilogy is not optional—it is a strategic differentiator. We acquire software companies at speed and scale them rapidly. Sustaining this pace requires executives who design and implement lean, automated systems rather than expand complexity through additional headcount. You will take ownership of complete operational transformations across our global portfolio. This might involve redesigning the offboarding process for 1,200+ employees following an acquisition, replacing platforms like Jira and Salesforce with AI-driven agents, or creating 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—alongside a library of battle-tested playbooks that keep you focused on results. Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We maintain fewer organizational layers, shorter decision cycles, and higher performance standards than conventional enterprise settings. This represents an opportunity to deliver meaningful impact at scale without navigating bureaucracy or managing oversized teams. Steady-state operations are not part of our model. We do not outsource transformation. And we do not hire individuals who require approval or large teams to execute. We seek a select group of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as a competitive advantage. If this describes you—this environment is where you will excel. What You Will Be Doing

• Driving high-complexity operational 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-powered workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
• Owning initiatives end-to-end—from assessment through deployment—leveraging proven playbooks and senior-level judgment
• Demonstrating technical capability through a hands-on challenge designed to assess your ability to design and ship AI-first solutions

What You Won’t Be Doing

• Building or managing large teams or depending on organizational layers to deliver outcomes
• Attending protracted alignment sessions or waiting for consensus before taking action
• Outsourcing critical work to IT departments or external vendors—you will design and implement solutions directly
• Running steady-state operations—this role centers on transformation and execution speed

Head Of Operations Key Responsibilities Architect and implement AI-first operational systems that remove manual work, reduce complexity, and enable scalable execution across Trilogy's global software portfolio. Basic Requirements

• Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
• 5+ years of operational leadership within enterprise software
• 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
• Proven ability to build automation using Python and integrate with LLM APIs
• Experience deploying production-grade automations using Cursor, Windsurf, MCP, or comparable tools
• Demonstrated capacity to execute rapidly, think autonomously, and deliver critical results without supervision

Nice-to-have Requirements

• Track record leading large-scale organizational transitions including M&A integrations or mass offboarding
• Experience architecting and deploying AI-driven operational systems
• Portfolio demonstrating automations you have personally developed and deployed at scale

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.002 Apply tot his job Apply To this Job