Description
This position is designed for operators capable of designing and redesigning scalable systems from the ground up.
Operational excellence at Trilogy is not optional—it is a core competitive edge. We move quickly to acquire software companies and scale them at even greater speed. Sustaining this pace requires executives who can architect lean, automated infrastructure—not those who respond to complexity by adding headcount.
You will take ownership of complete transformations spanning our global portfolio. This might include restructuring the offboarding process for over 1,200 employees following acquisitions, substituting Jira and Salesforce with AI-driven agents, or creating automation frameworks that remove thousands of hours of manual effort. Execution will be fast, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep your focus on results.
Trilogy operates a portfolio of 100+ products with discipline and efficiency. We maintain fewer management layers, shorter execution cycles, and stricter performance standards than conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
Steady-state operations are not part of our model. We do not delegate transformation to third parties. We do not recruit individuals who require extensive approval chains or large support structures to deliver results. We seek a select group of highly technical, execution-oriented leaders who treat automation as leverage and speed as a strategic principle. If this describes you—you will excel in this environment.
What you will be doing
- Delivering high-complexity operational initiatives including M&A integrations, enterprise platform migrations, and organization-wide transitions
- Building and launching automation systems that 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 reduce cycle time
- Owning projects end-to-end from initial assessment through deployment, applying established playbooks and senior-level decision-making
What you will NOT be doing
- Building or overseeing large teams or depending on multiple organizational layers to achieve outcomes
- Attending prolonged coordination meetings or waiting for group consensus before taking action
- Handing off complex technical work to IT departments or outside contractors—you will design and implement solutions directly
- Running steady-state operations—this role centers on continuous transformation and rapid execution
Key responsibilities
Architect and implement AI-first operational frameworks that remove manual tasks, reduce structural complexity, and enable scalable execution throughout Trilogy's worldwide software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience making presentations to C-suite executives
- Experience writing automation in Python and integrate with LLM APIs
- Experience using Cursor, Windsurf, MCP, or similar tools to ship 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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