Operations AI Lead, Trilogy (Remote)

This role is built for operators who engineer and re-engineer systems designed to scale.

Operational excellence at Trilogy is not optional—it's our competitive edge. We acquire software companies at speed and scale them even faster. To sustain this, we require leaders capable of architecting lean, automated systems—not expanding complexity through additional headcount.

You will take ownership of complete transformations spanning our global portfolio. This may involve redesigning the offboarding process for over 1,200 employees following an acquisition, replacing enterprise tools like Jira and Salesforce with AI-driven agents, 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 library of battle-tested playbooks that keep you focused on results.

Trilogy operates a portfolio of 100+ products with uncompromising efficiency. We run with fewer organizational layers, shorter cycles, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate impact at scale without navigating bureaucracy or overseeing large teams.

We do not engage in steady-state operations. Transformation is never outsourced. And we do not hire individuals who require permission or extensive teams to deliver. We are seeking a select group of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as core strategy. If this describes you—you will excel here.

What You Will Be Doing

• Executing operationally complex projects including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Architecting and delivering 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 execution latency
• Driving initiatives end-to-end from diagnosis through deployment, applying proven playbooks and executive decision-making
• Completing a practical technical challenge that validates your capability to design and deliver AI-first solutions

What You Won’t Be Doing

• Overseeing large teams or depending on multiple layers of people to achieve results
• Attending prolonged alignment meetings or waiting for consensus before taking action
• Handing off the difficult work to IT departments or external vendors—you will design and execute the solution directly
• Running steady-state operations—this role is centered on transformation and execution speed

Operations AI Lead 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-GB-London-OperationsAILe.001