Description
We're seeking operators capable of designing and redesigning systems built to scale.
Operational excellence at Trilogy isn't optional—it's the foundation of our competitive edge. We move quickly to acquire software companies, then scale them even more aggressively. Sustaining this pace demands executives who can architect lean, automated infrastructure—not layer in complexity through headcount expansion.
You'll take ownership of complete transformations spanning our global portfolio. Projects might include redesigning the offboarding process for 1,200+ employees following an acquisition, replacing platforms like Salesforce and Jira with AI-powered agents, or deploying automations that remove thousands of hours of manual effort. Execution speed matters: you'll work with Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—plus a library of battle-tested playbooks that allow you to prioritize results.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We maintain fewer organizational layers, shorter decision cycles, and more demanding standards than conventional enterprise settings. This position offers the opportunity to create large-scale impact without navigating bureaucratic friction or overseeing oversized teams.
Steady-state operations aren't our focus. We don't delegate transformation externally. And we don't bring on people who require extensive approvals or large teams to perform. We're selecting a limited number of highly technical, execution-driven leaders who treat automation as force multiplication and velocity as core strategy. If this describes your approach—this environment will suit you well.
What you will be doing
- Driving high-complexity operational initiatives including M&A integration, enterprise platform migration, and organization-wide transitions
- Building and launching automations that replace CRM and task management platforms through Python and LLM APIs
- Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and shorten cycle times
- Owning projects end-to-end—from initial assessment through final deployment—guided by established playbooks and executive-caliber decision-making
- Working through a practical technical assessment to validate your capability in designing and deploying AI-native solutions
What you will NOT be doing
- Building or managing large teams, or depending on organizational layers to achieve outcomes
- Participating in prolonged alignment sessions or waiting for consensus before taking action
- Handing off technical execution to IT departments or third-party vendors—you'll design and implement solutions directly
- Operating in maintenance mode—this position centers on transformation and rapid delivery
Key responsibilities
Architect and implement AI-native operational systems that remove manual tasks, reduce structural complexity, and enable scalable execution across Trilogy's worldwide software portfolio.
Candidate 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
You will be working for
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