Description
This position is designed for operators capable of designing and redesigning systems built for scale.
Operational excellence at Trilogy is not optional—it is a core competitive advantage. We move quickly to acquire software companies and even more quickly to scale them. Sustaining this pace requires executives who can architect lean, automated infrastructure—not expand operations through additional headcount.
You will take ownership of comprehensive transformations spanning our global portfolio. Examples include redesigning the offboarding workflow for over 1,200 employees following acquisitions, replacing Jira and Salesforce with AI-driven agents, or deploying 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 allow you to concentrate on results.
Trilogy manages a portfolio of more than 100 products with disciplined efficiency. We maintain fewer organizational layers, tighter execution cycles, and more rigorous standards than conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or overseeing oversized teams.
We do not operate in steady-state mode. We do not delegate transformation to third parties. And we do not bring on people who require extensive approval processes or large teams to deliver results. We are seeking a select group of technically deep, execution-oriented leaders who treat automation as leverage and velocity as a strategic asset. If this describes you—you will succeed here.
What you will be doing
- Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and organization-wide transitions
- Architecting and delivering automations to replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual processes and decrease latency
- Owning initiatives end-to-end—from diagnosis through deployment—leveraging established playbooks and executive judgment
- Completing a technical assessment designed to validate your capability to design and build AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple organizational layers to achieve outcomes
- Participating in prolonged alignment sessions or waiting for consensus to proceed
- Handing off complex work to IT departments or third-party vendors—you will design and execute the solution directly
- Running steady-state operations—this position centers on transformation and speed
Key responsibilities
Architect and implement AI-first operational infrastructure that removes manual work, reduces complexity, and enables scalable execution across Trilogy's global software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience delivering presentations to C-suite executives
- Experience developing automation using Python and integrating with LLM APIs
- Experience leveraging Cursor, Windsurf, MCP, or comparable tools to deliver production-grade automations
- Ability to work remotely with a minimum of 6 hours of overlap with the CST time zone
You will be working for
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