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

This position is designed for operators capable of designing and redesigning systems built to scale.
Operational excellence at Trilogy isn't optional—it's the competitive edge that sets us apart. Our business model depends on acquiring software companies quickly and scaling them even more rapidly. To maintain this pace, we require executives who architect lean, automated infrastructures—not those who address complexity by expanding headcount.
You'll be accountable for complete operational transformations spanning our international portfolio. Examples include redesigning the offboarding process for over 1,200 employees following acquisitions, substituting Jira and Salesforce with AI-driven agents, or creating automation that removes thousands of hours of manual effort. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by battle-tested playbooks that allow you to concentrate on measurable results.
Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We function with reduced organizational layers, accelerated delivery cycles, and elevated performance standards compared to conventional enterprise settings. This opportunity allows you to generate meaningful impact at scale without navigating bureaucratic obstacles or supervising oversized teams.
Steady-state operations aren't part of our mandate. Transformation isn't something we delegate externally. And we don't bring on individuals who require approval or large teams to produce results. We're seeking a select group of deeply technical, execution-oriented leaders who treat automation as force multiplication and velocity as competitive strategy. If this describes you—this environment will suit you exceptionally well.
What You Will Be Doing

• Driving operationally complex initiatives including M&A integrations, enterprise-level system migrations, and organization-wide transitions
• Building and launching automations that replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and cut latency
• Owning initiatives from initial assessment through full deployment, applying proven playbooks and executive decision-making
• Completing a practical technical assessment to validate your capability to architect and deliver AI-first solutions
  

What You Won’t Be Doing

• Building or 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 challenging technical work to IT departments or third-party vendors—you'll design and implement solutions directly
• Running steady-state operations—this position centers on transformation and rapid execution
  

Operations AI Lead Key Responsibilities
Architect and implement AI-first operational infrastructures that remove manual workload, reduce operational 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
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