Description
This position is designed for operators who excel at building and reengineering systems that scale effectively.
Operational excellence at Trilogy is not optional—it is a core competitive advantage. We move quickly to acquire software companies and scale them at an accelerated pace. To sustain this momentum, we require executives capable of designing and implementing lean, automated systems rather than adding layers of management overhead.
You will take ownership of comprehensive transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 1,200 employees following an acquisition, replacing legacy platforms like Jira and Salesforce with AI-driven agents, or developing automations that remove thousands of manual hours from workflows. Execution will be rapid, using Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that allow you to concentrate on results.
Trilogy manages a portfolio of more than 100 products with strict efficiency. We operate with reduced hierarchy, compressed cycles, and elevated standards compared to conventional enterprise settings. This opportunity allows you to generate large-scale impact without navigating bureaucracy or overseeing oversized teams.
Steady-state operations are not part of our model. We do not outsource transformation efforts. And we do not bring on individuals who require extensive approval chains or large teams to deliver results. We are seeking a select group of deeply technical, execution-oriented leaders who treat automation as leverage and speed as a strategic asset. If that 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 large-scale organizational transitions
- Building and deploying automations that replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
- Driving initiatives from initial assessment through full deployment, applying proven playbooks and executive-level decision-making
- Successfully completing a hands-on technical assessment to validate your capability to design and deliver AI-first solutions
What you will NOT be doing
- Building or managing large teams, or depending on multiple layers of staff to execute deliverables
- Participating in prolonged alignment meetings or waiting for consensus before taking action
- Handing off the complex work to IT departments or third-party vendors—you will architect and implement the solution directly
- Operating in a steady-state maintenance mode—this role is centered on transformation and speed
Key responsibilities
Architect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience delivering presentations to C-suite executives
- Experience building automation using Python and integrating with LLM APIs
- Experience leveraging Cursor, Windsurf, MCP, or comparable tools to deliver production-grade automations
- Ability to work remotely with a minimum of 6 hours of overlap with the CST time zone
You will be working for
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