Description
This position is designed for operators capable of constructing and reconstructing systems that scale effectively.
Operational excellence at Trilogy is not optional—it is a core competitive advantage. We acquire software companies rapidly and accelerate their growth even more quickly. To sustain this pace, we require executives who can architect and implement lean, automated systems rather than address complexity through additional headcount.
You will oversee complete transformations spanning our global portfolio in this capacity. This might involve redesigning the offboarding process for more than 1,200 employees following acquisitions, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of manual work hours. Execution will be swift, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of proven playbooks that enable you to concentrate on results.
Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This represents an opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
Steady-state operations are not our focus. Transformation is never outsourced. And we do not bring on individuals who require permission or extensive teams to produce results. We seek a select group of highly technical, execution-oriented leaders who leverage automation and treat speed as a strategic asset. If this describes you—this environment will suit you well.
What you will be doing
- Delivering high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
- Architecting and launching automations to 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 decrease latency
- Driving projects from assessment through deployment, applying proven playbooks and executive judgment
What you will NOT be doing
- Overseeing large teams or depending on multiple organizational layers to accomplish work
- Participating in prolonged alignment sessions or waiting for consensus to proceed
- Handing off the complex work to IT departments or third-party vendors—you will design and implement the solution directly
- Running steady-state operations—this position centers on transformation and rapid execution
Key responsibilities
Architect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution throughout Trilogy's global 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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