Operations AI Lead, Trilogy (Remote) - $200,000/year USD

This position is designed for operators who excel at creating and re-engineering scalable systems.
Operational excellence at Trilogy is not optional—it's what gives us a competitive edge. We move quickly to acquire software companies and accelerate their growth even faster. To maintain this pace, we require executives capable of architecting and implementing efficient, automated systems—not those who rely on expanding headcount to handle complexity.
You'll take ownership of comprehensive transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI-driven agents, or creating automation that removes thousands of hours of manual work. Using Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP, you'll move quickly—supported by a collection of battle-tested playbooks that allow you to concentrate on results.
Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We work with reduced organizational layers, accelerated cycles, and elevated standards compared to conventional enterprise settings. This opportunity allows you to generate large-scale impact without navigating bureaucracy or overseeing oversized teams.
We reject static operational models. We keep transformation in-house. And we don't bring on individuals who require extensive approval chains or large teams to execute. We seek a select group of highly technical, execution-focused leaders who treat automation as a force multiplier and speed as a core strategy. If this describes you—you'll excel in this environment.
What You Will Be Doing

• Delivering high-complexity operational initiatives including M&A integrations, enterprise system transitions, and organization-wide changes
• Building and launching automations that supplant CRM and task management platforms through Python and LLM APIs
• Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and decrease delays
• Owning projects from assessment through delivery, applying established playbooks and senior-level decision-making
  

What You Won’t Be Doing

• Overseeing large teams or depending on multiple layers of personnel to accomplish objectives
• Participating in prolonged alignment sessions or waiting for consensus before taking action
• Handing off the complex technical work to IT departments or outside contractors—you'll design and build the solution directly
• Running steady-state operations—this position centers on transformation and rapid execution
  

Operations AI Lead Key Responsibilities
Architect and implement AI-first operational frameworks that remove manual tasks, reduce complexity, and enable scalable execution throughout Trilogy's worldwide 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-NG-Lagos-OperationsAILe.002
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