Description
We are seeking operators capable of constructing and reconstructing systems designed to scale effectively.
Operational excellence at Trilogy is not optional—it is our competitive edge. We acquire software companies rapidly and scale them even more quickly. Sustaining this pace requires executives who can architect and implement lean, automated systems rather than address complexity through expanded headcount.
This position entails ownership of complete transformations spanning our global portfolio. Examples include redesigning offboarding processes for 1,200+ employees following acquisitions, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of manual hours. Execution velocity is achieved using Python, LLM APIs, tools such as Cursor, Windsurf, and MCP—alongside a library of established playbooks enabling focus on results.
Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We function with reduced hierarchies, accelerated cycles, and elevated standards compared to conventional enterprise settings. This opportunity allows you to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.
Steady-state operations are not our model. Transformation is never outsourced. We do not recruit individuals requiring permission or extensive teams to deliver results. Our search is for a limited number of highly technical, execution-oriented leaders who leverage automation and prioritize speed as strategy. If this describes you—this environment will suit you well.
What you will be doing
- Leading high-complexity operational initiatives including M&A integrations, enterprise system migrations, and organization-wide transitions
- Architecting and deploying automations to replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and decrease latency
- Driving projects from diagnosis through deployment, applying established playbooks and executive-caliber judgment
- Completing a practical technical challenge demonstrating your capability to design and deliver AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on multiple layers of personnel to accomplish objectives
- Participating in prolonged alignment meetings or waiting for consensus to advance
- Handing off complex work to IT departments or external vendors—you will design and execute the solution directly
- Operating in steady-state mode—this position centers on transformation and speed
Key responsibilities
Architect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution throughout Trilogy's global 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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