Description
This position is designed for operators capable of constructing and reconstructing scalable systems.
Operational excellence at Trilogy is not optional—it is the foundation of our competitive edge. We move quickly to acquire software companies and scale them with even greater speed. Sustaining this requires executives who architect lean, automated systems rather than absorbing complexity through expanded headcount.
You will own complete transformations throughout our global portfolio in this capacity. This may involve redesigning the offboarding process for 1,200+ employees following acquisitions, substituting Jira and Salesforce with AI agents, or creating automations that eradicate thousands of manual hours. 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 enable you to concentrate on results.
Trilogy operates a portfolio of 100+ products with disciplined efficiency. Our structure has fewer layers, shorter cycles, and more demanding standards than conventional enterprise settings. This opportunity allows you to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
We do not engage in maintenance-mode operations. We do not delegate transformation externally. And we do not bring on individuals who require approval or extensive teams to produce results. Our search is for a select group of technically proficient, execution-oriented leaders who leverage automation for multiplied effect and treat speed as a strategic asset. If this describes you—this environment will suit you well.
What you will be doing
- Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
- Architecting and deploying automations to replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and compress cycle times
- Owning initiatives end-to-end—from initial diagnosis through final deployment—applying proven playbooks and executive judgment
- Completing a technical challenge that requires you to design and build AI-first solutions hands-on
What you will NOT be doing
- Building or managing large teams or depending on organizational layers to execute
- Participating in prolonged alignment meetings or waiting for consensus before taking action
- Handing off difficult work to IT departments or third-party vendors—you will design and execute the solution directly
- Operating in steady-state mode—this role centers 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 portfolio of software products.
Candidate requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years leading operations in enterprise software environments
- 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
- Proven capability to develop automation using Python and integrate with LLM APIs
- Experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable tools
- Track record of moving quickly, thinking independently, and delivering high-impact outcomes without supervision
Nice to have
- Background leading large-scale organizational changes including M&A integrations or mass offboarding initiatives
- Track record designing and launching AI-powered operational systems
- Collection of automations you have personally developed and deployed at scale
You will be working for
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