Operations AI Lead $200,000 USD/year Pay is set based on global value, not the local market.
Most roles = hourly rate x 40 hrs x 50 weeks
Not accepting applications on crossover.com at this time.
Description
This position is designed for operators capable of constructing and reconstructing scalable systems from the ground up.
Operational excellence at Trilogy is not optional—it is a strategic differentiator. We complete software company acquisitions rapidly and accelerate their growth even more aggressively. Sustaining this pace requires executives who can architect lean, automated infrastructure rather than add layers of management overhead.
You will take ownership of complete transformations spanning our international portfolio. This might involve redesigning the offboarding process for 1,200+ employees following an acquisition, substituting Jira and Salesforce with AI-powered agents, or creating automations that remove thousands of hours of manual labor. Execution will be swift, leveraging Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that allow you to concentrate on results.
Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We function with reduced organizational layers, accelerated delivery cycles, and more demanding standards than conventional enterprise settings. This represents an opportunity to generate large-scale impact without navigating bureaucratic obstacles or overseeing inflated teams.
Steady-state operations are not our domain. Transformation is never outsourced. We do not recruit individuals who require approval chains or extensive teams to produce results. Our search is for a limited number of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as core strategy. If this describes you—this environment will suit you exceptionally well.
What you will be doing
- Delivering high-complexity operational initiatives including M&A integration projects, enterprise-scale system migrations, and comprehensive organizational transitions
- Architecting and deploying automations that supplant CRM and task coordination platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and decrease response times
- Driving projects from initial assessment through full deployment, applying established playbooks and senior-level decision-making
- Passing a practical technical assessment that validates your capacity to design and execute AI-centric solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple organizational layers to accomplish objectives
- Attending prolonged alignment sessions or waiting for consensus before taking action
- Assigning complex technical work to IT departments or third-party contractors—you will design and build the solution directly
- Running steady-state operations—this position centers on transformation and rapid execution
Key responsibilities
Architect and implement AI-driven operational frameworks that remove manual workload, reduce complexity, and enable scalable execution throughout Trilogy's worldwide software portfolio.
Candidate requirements
- 5+ years leading operational functions in business operations
- Demonstrated experience delivering presentations to C-suite leadership
- Hands-on experience building automation scripts in Python and integrating with LLM APIs
- Proven ability using Cursor, Windsurf, MCP, or equivalent platforms to deliver production-quality automations
- Ability to work remotely with a minimum of 6 hours overlap with the CST time zone
You will be working for
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