Description
This position is designed for operators capable of designing and redesigning systems built for scale.
Operational excellence at Trilogy is not optional—it is the foundation of our competitive edge. We acquire software companies rapidly and accelerate their growth even more quickly. To sustain this pace, we require executives who can architect lean, automated systems rather than solve problems by expanding teams.
You will take ownership of complete transformations spanning our global portfolio. This might include redesigning the offboarding process for over 1,200 employees following an acquisition, replacing platforms like Jira and Salesforce with AI-powered agents, or deploying automations that remove thousands of hours of manual effort. You will move quickly, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—backed by a library of validated playbooks that keep your focus on results.
Trilogy manages a portfolio of more than 100 products with relentless efficiency. We function with fewer organizational layers, tighter cycles, and more demanding standards than conventional enterprise settings. This is an opportunity to create large-scale impact without navigating bureaucratic friction or overseeing oversized teams.
We do not operate in steady-state mode. We do not outsource our transformation work. And we do not bring on people who require approval or significant headcount to execute. We are seeking a select group of deeply technical, execution-oriented leaders who treat automation as a force multiplier and speed as a core strategy. If that describes you—this is where you belong.
What you will be doing
- Leading high-complexity operational initiatives including M&A integrations, enterprise platform migrations, and large-scale organizational transitions
- Building and deploying automations to replace CRM and task management systems using Python and LLM APIs
- Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
- Driving initiatives end-to-end—from diagnosis through deployment—applying proven playbooks and executive judgment
What you will NOT be doing
- Building or managing large teams, or depending on organizational depth to achieve results
- Spending time in prolonged alignment sessions or waiting for group consensus before proceeding
- Handing off technical execution to IT departments or third-party vendors—you will design and implement solutions directly
- Running steady-state operations—this role centers on transformation and rapid execution
Key responsibilities
Architect and implement AI-first operational systems that remove manual workloads, simplify complexity, and enable scalable execution across Trilogy's worldwide software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience presenting to C-suite executives
- Experience building automation in Python and integrating with LLM APIs
- Experience using 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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