Description
This position is designed for operators who excel at building systems capable of scaling rapidly.
Operational excellence at Trilogy is not optional—it is the foundation of our competitive edge. We move quickly to acquire software companies and scale them at an accelerated pace. Success demands leaders who can architect lean, automated systems rather than expand headcount to absorb complexity.
You will take ownership of complete operational transformations across our worldwide portfolio. Projects may include redesigning the offboarding process for over 1,200 employees following acquisitions, substituting Jira and Salesforce with AI-driven agents, or implementing automation that removes 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 designed to prioritize results.
Trilogy manages a portfolio exceeding 100 products with uncompromising efficiency. We operate with reduced hierarchies, shorter cycles, and elevated standards compared to conventional enterprise settings. This opportunity allows you to generate measurable impact at scale without navigating bureaucratic obstacles or overseeing inflated teams.
Steady-state operations are not part of our model. Transformation is never outsourced. And we do not bring on individuals who require approval or extensive teams to execute. We seek a select group of highly technical, execution-oriented leaders who treat automation as leverage and speed as a fundamental strategy. 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
- Building and deploying 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 analysis to launch, guided by established playbooks and executive judgment
- Completing a practical technical assessment to validate your capability to architect and execute AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple layers of personnel to achieve results
- Attending prolonged alignment sessions or waiting for consensus to proceed
- Assigning the complex technical work to IT departments or third-party vendors—you will design and implement solutions directly
- Operating in steady-state mode—this position centers on transformation and rapid execution
Key responsibilities
Architect and implement AI-first operational systems that remove manual processes, reduce complexity, and enable scalable execution throughout Trilogy's global 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 utilizing 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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