Description
This position is designed for operators who build and redesign systems that can scale.
Operational excellence at Trilogy is not a secondary goal—it is the foundation of our competitive edge. We acquire software companies at pace and scale them faster still. To sustain that momentum, we require executives capable of designing and implementing lean, automated systems—not solving complexity by adding people.
You will be responsible for end-to-end transformations throughout our global portfolio. This could involve redesigning how we offboard over 1,200 employees following an acquisition, replacing Jira and Salesforce with AI agents, or developing automations that remove thousands of hours of manual effort. You will execute quickly using Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a collection of proven playbooks that allow you to concentrate on results.
Trilogy operates a portfolio of more than 100 products with disciplined efficiency. We maintain fewer organizational layers, shorter cycles, and more rigorous expectations than conventional enterprise settings. This is an opportunity to generate impact at scale without navigating bureaucracy or overseeing inflated teams.
We do not engage in steady-state operations. We do not delegate transformation to third parties. And we do not recruit people who require approval or large teams to deliver results. We are seeking a limited number of deeply technical, execution-focused leaders who leverage automation and treat speed as strategic advantage. If this describes you—this environment will suit you.
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 eliminate manual tasks and reduce cycle time
- Owning initiatives from assessment through deployment, leveraging proven playbooks and executive judgment
- Completing a practical technical challenge that demonstrates your capability to design and deliver AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple layers of personnel to achieve outcomes
- Participating in prolonged alignment meetings or waiting for consensus to proceed
- Delegating complex work to IT departments or external vendors—you will design and implement the solution directly
- Operating in steady-state mode—this role centers on transformation and speed
Key responsibilities
Design and implement AI-first operational systems that remove manual work, reduce complexity, and enable scalable execution across Trilogy's global 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 in enterprise software
- 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
- Proven capability to build automation in Python and integrate with LLM APIs
- Experience deploying production-grade automations using Cursor, Windsurf, MCP, or equivalent tools
- Demonstrated ability to execute quickly, think independently, and deliver high-stakes outcomes without supervision
Nice to have
- Track record leading large-scale organizational transitions including M&A integrations or mass offboarding
- Background in designing and implementing AI-driven operational systems
- Portfolio of automations you have personally developed and deployed at scale
You will be working for
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