Description
This position is designed for operators capable of building and reconstructing systems at scale.
Operational excellence at Trilogy is not optional—it's a core competitive advantage. We move quickly to acquire software companies and scale them even more rapidly. Sustaining this pace requires executives who design and implement lean, automated systems rather than add complexity through headcount expansion.
You will be accountable for complete transformations spanning our international portfolio. This might include redesigning the offboarding process for 1,200+ employees following acquisition, substituting Jira and Salesforce with AI-driven agents, or creating automations that remove thousands of hours of manual work. Execution will be swift, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—alongside 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 fewer hierarchies, accelerated timelines, and elevated standards compared to conventional enterprise settings. This represents an opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
We do not perform maintenance-mode operations. We do not delegate transformation externally. And we do not recruit individuals who require approval or extensive teams to produce results. We seek a select group of highly technical, execution-oriented leaders who treat automation as a force multiplier and speed as a core strategy. If this describes you—you will excel here.
What you will be doing
- Delivering complex operational projects including M&A integrations, enterprise-scale system migrations, and organization-wide transitions
- Architecting and deploying automations that substitute for CRM and task management platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual tasks and decrease response time
- Driving initiatives end-to-end—from analysis through deployment—applying established playbooks and executive-caliber decision-making
- Successfully completing a practical technical assessment 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 accomplish objectives
- Participating in protracted alignment sessions or waiting for consensus before taking action
- Handing off difficult work to IT departments or third-party vendors—you will design and build the solution directly
- Operating in steady-state mode—this position centers on transformation and rapid execution
Key responsibilities
Architect and launch AI-first operational systems that remove manual processes, reduce complexity, and enable scalable execution throughout Trilogy's worldwide software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience delivering presentations to C-suite executives
- Experience building automation in 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 overlap with the CST time zone
You will be working for
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