Description
This position is designed for operators capable of architecting and re-architecting systems at scale.
Operational excellence at Trilogy is not optional—it serves as our competitive edge. We execute rapid acquisitions of software companies and accelerate their growth even faster. Sustaining this pace demands executives who engineer lean, automated frameworks rather than layer on workforce to absorb complexity.
You will take full ownership of transformations spanning our worldwide portfolio. This might include redesigning offboarding workflows for over 1,200 employees following acquisition, substituting Jira and Salesforce with AI-driven agents, or creating automations that remove thousands of hours of manual labor. 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 keep your focus on results.
Trilogy manages a portfolio of more than 100 products with disciplined efficiency. We function with reduced hierarchies, compressed timelines, and elevated standards compared to conventional enterprise settings. This opportunity allows you to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
Steady-state operations are not our model. Transformation is not outsourced. We do not recruit individuals who require approval or extensive teams to deliver results. Our search is for a select group of technically proficient, execution-oriented leaders who treat automation as leverage and velocity as strategy. If that describes you—this environment will suit you well.
What you will be doing
- Delivering high-complexity operational initiatives including M&A integrations, enterprise system overhauls, and large-scale organizational transitions
- Building and deploying automations that supplant CRM and task management platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and cut cycle time
- Driving projects from root-cause analysis through to deployment, applying proven playbooks and executive judgment
- Completing a practical technical assessment to validate your capability to architect and deliver AI-first systems
What you will NOT be doing
- Overseeing large teams or depending on multiple layers of personnel to execute
- Attending prolonged alignment sessions or waiting for consensus before advancing
- Handing off the complex work to IT departments or third-party contractors—you will design and implement solutions directly
- Running steady-state operations—this position centers on transformation and speed
Key responsibilities
Architect and implement AI-first operational frameworks that remove manual effort, simplify complexity, and enable scalable execution across Trilogy's international 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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