Description
This position is designed for operators who architect and reimagine systems built to scale.
Operational excellence at Trilogy is not a secondary objective—it is our competitive edge. We acquire software companies rapidly and expand them faster still. Sustaining this velocity demands executives capable of architecting and implementing lean, automated infrastructure—without scaling complexity through headcount.
You will take ownership of comprehensive transformations spanning our global portfolio. Examples include restructuring the offboarding process for 1,200+ employees following acquisition, replacing platforms like Jira and Salesforce with AI agents, or creating automations that remove thousands of manual hours from workflows. Execution will be swift, leveraging Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks focused on measurable outcomes.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We maintain fewer organizational layers, shorter iteration cycles, and more demanding performance standards than conventional enterprise settings. This represents an opportunity to generate meaningful impact at scale, free from bureaucratic friction or the burden of oversized teams.
Steady-state operations are not our focus. Transformation is not outsourced. And we do not bring on individuals who require extensive approval chains or large teams to achieve results. We seek a select group of deeply technical, execution-oriented leaders who treat automation as leverage and speed as core strategy. If this describes your approach—this environment will suit you well.
What you will be doing
- Leading high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
- Architecting and delivering 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 effort and decrease latency
- Driving projects from initial diagnosis through full deployment, applying proven playbooks and executive judgment
- Completing a technical assessment designed to validate your capability to design and deploy AI-first solutions
What you will NOT be doing
- Building or managing large teams, or depending on organizational layers to execute
- Attending prolonged alignment sessions or waiting for consensus before taking action
- Handing off complex work to IT departments or third-party vendors—you will design and implement solutions directly
- Running steady-state operations—this role centers on transformation and execution 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 in enterprise software
- 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
- Proven ability to write automation in Python and integrate with LLM APIs
- Experience shipping production-grade automations using Cursor, Windsurf, MCP, or similar tools
- Demonstrated capacity to execute quickly, think independently, and deliver high-stakes outcomes without supervision
Nice to have
- Track record leading large-scale organizational transitions such as M&A integrations or mass offboarding
- Background in designing and deploying AI-driven operational systems
- Portfolio of automations you have personally developed and deployed at scale
You will be working for
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