Description
This position is designed for operators capable of constructing and reconstructing scalable systems.
Operational excellence at Trilogy represents a core competitive advantage, not an optional feature. Our approach involves acquiring software companies rapidly and scaling them with even greater speed. Sustaining this requires executives who can architect and implement lean, automated systems—rather than addressing complexity through additional personnel.
This role encompasses ownership of complete transformations spanning our global portfolio. Examples include redesigning the offboarding process for 1,200+ employees following acquisition, substituting Jira and Salesforce with AI agents, or developing automations that remove thousands of manual hours from operations. Execution will be rapid, leveraging Python, LLM APIs, tools such as Cursor, Windsurf, and MCP—supported by a collection of established playbooks that enable concentration on results.
Trilogy maintains a portfolio exceeding 100 products with disciplined efficiency. Our structure features reduced organizational layers, accelerated cycles, and elevated standards compared to conventional enterprise settings. This represents an opportunity to generate large-scale impact without navigating bureaucracy or supervising oversized teams.
We do not engage in steady-state operations. Transformation is not outsourced. We do not recruit individuals requiring approval or substantial teams to produce results. Our search is for a limited number of highly technical, execution-oriented leaders who employ automation as leverage and velocity as strategy. If this describes you—this environment will suit you well.
What you will be doing
- Leading operationally complex projects including M&A integrations, enterprise system migrations, and organizational transitions at scale
- Architecting and delivering automations that supplant CRM and task management platforms through Python and LLM APIs
- Implementing AI-driven workflows using Cursor, Windsurf, and MCP to remove manual processes and decrease latency
- Driving initiatives from initial assessment through final deployment, applying established playbooks and executive-caliber decision-making
What you will NOT be doing
- Overseeing large teams or depending on multiple organizational layers to accomplish objectives
- Participating in prolonged alignment sessions or waiting for consensus before taking action
- Assigning complex technical work to IT departments or third-party vendors—you will design and implement solutions directly
- Operating in steady-state maintenance 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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