Description
This position is designed for operators capable of constructing and reconstructing scalable systems.
Operational excellence at Trilogy is not optional—it's a competitive edge. We acquire software businesses rapidly and accelerate their growth even more quickly. Sustaining this pace requires executives who can architect and implement streamlined, automated systems rather than address complexity through additional personnel.
You will take full ownership of transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI agents, or creating automations that remove 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 that allow you to concentrate on results.
Trilogy manages a portfolio of more than 100 products with disciplined efficiency. We function with reduced organizational layers, accelerated timelines, and elevated performance standards compared to conventional enterprise settings. This represents an opportunity to generate meaningful impact at scale, free from bureaucratic friction or the burden of overseeing large teams.
Steady-state operations are not our focus. Transformation is not outsourced. And we do not recruit individuals who require approval or extensive teams to produce results. We seek a limited number of highly technical, execution-oriented leaders who apply automation as a force multiplier and velocity as a core tactic. If this describes you, you will excel in this environment.
What you will be doing
- Executing operationally complex projects including M&A integrations, enterprise-level system migrations, and large-scale organizational transitions
- Architecting 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 decrease latency
- Driving initiatives from initial diagnosis through final deployment, guided by established playbooks and executive-caliber decision-making
- Completing a practical technical assessment to validate your capacity to design and deliver AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple organizational layers to achieve outcomes
- Participating in protracted alignment meetings or waiting for consensus before taking action
- Handing off challenging work to IT departments or third-party vendors—you will design and execute the solution directly
- Supporting steady-state operations—this position centers on transformation and speed
Key responsibilities
Architect and implement AI-first operational systems that remove manual work, reduce complexity, and enable scalable execution throughout Trilogy's worldwide software portfolio.
Candidate requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years of operational leadership within enterprise software
- 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
- Proven capability to write automation using Python and integrate with LLM APIs
- Experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable tools
- Demonstrated ability to execute rapidly, think autonomously, and deliver high-stakes outcomes without guidance
Nice to have
- Background leading large-scale organizational transitions including M&A integrations or mass offboarding
- Track record of architecting and launching AI-driven operational systems
- Collection of automations you have personally developed and deployed at scale
You will be working for
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