Description
This position is designed for operators capable of constructing and reconstructing systems built to scale.
Operational excellence at Trilogy isn't optional—it's the competitive edge that sets us apart. We acquire software companies rapidly and scale them even more aggressively. Sustaining this pace requires executives who can architect and implement lean, automated systems rather than solving problems by adding headcount.
You'll take ownership of complete transformations spanning our global portfolio. This might involve redesigning the offboarding process for 1,200+ employees following an acquisition, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of manual hours from operations. Execution will be rapid, 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 exceeding 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 impact at scale without navigating bureaucracy or overseeing inflated teams.
We don't maintain steady-state operations. We don't delegate transformation to outside parties. And we don't bring on individuals who require approval or extensive teams to produce results. We're seeking a select group of deeply technical, execution-oriented leaders who leverage automation for multiplied impact and treat speed as strategic doctrine. If this describes you—you'll excel here.
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 that 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 reduce execution latency
- Driving projects from initial diagnosis through full deployment, applying proven playbooks and executive-caliber judgment
- Successfully completing a practical technical assessment to validate your capability to design and execute AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple layers of personnel to accomplish objectives
- Participating in prolonged alignment meetings or waiting for consensus before taking action
- Handing off the challenging work to IT departments or external vendors—you'll design and build 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, simplify 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 developing automation in Python and integrating with LLM APIs
- Experience leveraging Cursor, Windsurf, MCP, or comparable tools to deliver production-grade automations
- Remote work capability with a minimum of 6 hours overlap with the CST time zone
You will be working for
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