Description
This position is designed for operators with proven ability to architect and re-engineer systems at scale.
Operational excellence at Trilogy isn't optional—it's the foundation of our competitive edge. We acquire software companies rapidly and scale them even more aggressively. Success at this pace requires executives capable of creating lean, automated infrastructure—not solving problems by adding headcount.
You'll take ownership of comprehensive transformations across our worldwide portfolio. This might involve redesigning the offboarding process for 1,200+ employees following an acquisition, replacing Salesforce and Jira with AI-driven agents, or developing automations that remove thousands of hours of manual work. You'll move quickly using Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by battle-tested playbooks that keep you focused on results.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We function with minimal hierarchy, accelerated timelines, and expectations that exceed those of conventional enterprise settings. This is an opportunity to create impact at scale without navigating bureaucracy or supervising oversized teams.
Steady-state operations aren't part of our model. We don't outsource strategic transformation. And we don't hire individuals who require extensive permissions or large teams to execute. We're seeking a limited number of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as competitive strategy. If this describes you—this environment will suit you.
What you will be doing
- Driving high-complexity operational initiatives including M&A integrations, enterprise-level system migrations, and organization-wide transitions
- Building and launching automations that replace traditional CRM and task management platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
- Owning initiatives from initial assessment through final deployment, leveraging established playbooks and senior-level decision-making
- Passing a practical technical assessment to validate your capability to architect and deliver AI-first solutions
What you will NOT be doing
- Building or managing large teams, or depending on organizational layers to achieve results
- Attending continuous alignment sessions or waiting for consensus before taking action
- Handing off the challenging work to IT departments or third-party vendors—you'll design and implement the solution directly
- Running steady-state operations—this position centers on transformation and speed
Key responsibilities
Architect and implement AI-first operational infrastructure that removes manual workload, reduces complexity, and enables scalable execution across Trilogy's international software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience delivering presentations to C-suite executives
- Experience building automation in Python and integrating with LLM APIs
- Experience leveraging Cursor, Windsurf, MCP, or similar tools to deliver production-grade automations
- Remote work capability with at least 6 hours of overlap with the CST time zone
You will be working for
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