Description
This position is for operators capable of designing and redesigning systems built to scale.
Operational excellence at Trilogy is not optional—it is a competitive advantage. We acquire software businesses rapidly and scale them even more rapidly. Sustaining this pace requires executives who can architect lean, automated systems rather than solving complexity through headcount expansion.
You will be accountable for end-to-end operational transformations across our international portfolio. This may include redesigning offboarding workflows for 1,200+ employees following acquisitions, replacing Jira and Salesforce with AI 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—supported by a library of battle-tested playbooks that enable you to concentrate on results.
Trilogy operates a portfolio of 100+ products with disciplined efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
We do not maintain steady-state operations. We do not delegate transformation externally. And we do not hire individuals who require approval or extensive teams to execute. We are seeking a limited number of deeply technical, execution-oriented leaders who treat automation as leverage and speed as strategic doctrine. If this describes you—this environment will suit you.
What you will be doing
- Leading high-complexity operational initiatives including M&A integrations, enterprise-level 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-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce execution latency
- Driving projects from initial diagnosis through to full deployment, applying proven playbooks and exercising executive-level judgment
- Executing a hands-on technical challenge that demonstrates your capability to design and deliver AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple layers of personnel to accomplish objectives
- Participating in protracted alignment sessions or waiting for consensus before acting
- Handing off the technical work to IT departments or third-party vendors—you will design and execute the solution directly
- Supporting steady-state operations—this role is centered on transformation and speed
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.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience presenting to C-suite executives
- Experience writing automation in Python and integrating with LLM APIs
- Experience using Cursor, Windsurf, MCP, or similar tools to deliver production-grade automations
- Remote work capability with at least 6 hours of overlap with the CST time zone
You will be working for
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