Description
This position is built for operators capable of architecting and re-architecting systems designed for scalability.
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 velocity. Sustaining this pace requires executives who can architect lean, automated infrastructures—not absorb complexity through headcount expansion.
You will take ownership of comprehensive 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-driven agents, or creating automations that reclaim 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 field-tested playbooks that enable you to concentrate on measurable outcomes.
Trilogy manages a portfolio of 100+ products with precision and discipline. We function with reduced hierarchy, accelerated decision cycles, and more demanding standards than conventional enterprise settings. This role offers the opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
Steady-state operations are not our model. Transformation is not outsourced. We do not recruit individuals who require approval chains or expansive teams to execute. We seek a select group of deeply technical, execution-oriented leaders who treat automation as a force multiplier and speed as a strategic imperative. If this describes your approach—you will succeed here.
What you will be doing
- Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
- Building and deploying automations that replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual intervention and minimize latency
- Owning initiatives end-to-end, from initial assessment through full deployment, leveraging proven playbooks and executive judgment
- Passing a practical technical challenge that validates your capability to design and deliver AI-first solutions
What you will NOT be doing
- Building or managing large teams, or depending on multiple layers to achieve results
- Attending prolonged alignment sessions or waiting for consensus before taking action
- Handing off the complex work to IT departments or third-party vendors—you will design and implement the solution directly
- Running steady-state operations—this role is centered on transformation and rapid execution
Key responsibilities
Architect and implement AI-first operational infrastructures that remove manual processes, 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 leading operational functions in enterprise software environments
- 3+ years in customer-facing roles (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 equivalent tools
- Demonstrated ability to execute rapidly, think autonomously, and deliver critical results without supervision
Nice to have
- Background leading large-scale organizational transformations such as M&A integrations or mass offboarding events
- Track record of designing and launching AI-driven operational systems
- Personal portfolio of automations built and deployed at scale
You will be working for
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