Description
This role is for operators who design and deliver systems built to scale.
Operational excellence at Trilogy is not optional—it is our competitive edge. We acquire software companies rapidly and scale them even more quickly. To maintain this pace, we need executives who can architect and ship lean, automated systems—not add complexity through headcount expansion.
You will own complete transformations across our global portfolio. This might include redesigning the offboarding process for 1,200+ employees following an acquisition, replacing traditional tools like Jira and Salesforce with AI-powered agents, or creating automations that remove thousands of manual hours from workflows. You will move quickly using Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of proven playbooks that enable you to concentrate on delivering results.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We run with fewer organizational layers, shorter decision cycles, and higher performance standards than conventional enterprise settings. This is an opportunity to generate impact at scale without navigating bureaucracy or overseeing large teams.
We do not maintain steady-state operations. We do not outsource transformation work. And we do not hire individuals who require approval or extensive support structures to execute. We are seeking a limited number of deeply technical, execution-oriented leaders who treat automation as leverage and speed as competitive strategy. If that describes you—this is where you will succeed.
What you will be doing
- Leading 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 with Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
- Driving projects from assessment through deployment, applying proven playbooks and executive-level decision-making
- Completing a technical challenge that demonstrates your capability to design and execute AI-first operational solutions
What you will NOT be doing
- Building or managing large teams or depending on organizational layers to deliver outcomes
- Attending prolonged alignment sessions or waiting for consensus before taking action
- Handing off critical technical work to IT departments or third-party vendors—you will design and execute solutions directly
- Operating in steady-state mode—this role is centered on transformation and speed
Key responsibilities
Architect 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 experience in enterprise software
- 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
- Proven capability to build automation using Python and integrate with LLM APIs
- Experience deploying production-grade automations with Cursor, Windsurf, MCP, or equivalent tools
- Track record of moving quickly, thinking autonomously, and delivering high-stakes outcomes without supervision
Nice to have
- Background leading large-scale organizational transitions including M&A integrations or mass offboarding events
- Track record of architecting and deploying AI-driven operational systems
- Portfolio demonstrating automations you have built and scaled in production environments
You will be working for
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