Description
This is a role for operators capable of designing and rebuilding systems at scale.
Operational excellence at Trilogy isn't optional—it's the foundation of our competitive edge. We acquire software companies rapidly and scale them even faster. To sustain this pace, we require executives who can architect lean, automated systems rather than add layers of complexity through hiring.
You will take ownership of end-to-end transformations across our global portfolio. This might involve restructuring how we offboard 1,200+ employees following acquisitions, displacing Jira and Salesforce with AI agents, or creating automations that remove thousands of hours of manual labor. Execution will be fast, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—alongside a library of battle-tested playbooks that enable you to prioritize results.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We function with reduced hierarchy, accelerated timelines, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate impact at scale without navigating bureaucracy or overseeing bloated organizational structures.
Steady-state operations aren't part of our model. We don't delegate transformation to third parties. And we don't bring on people who require extensive approval or large teams to execute. We seek a select group of highly technical, execution-driven leaders who treat automation as leverage and velocity as core strategy. 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 to replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual effort and decrease cycle time
- Driving projects from initial assessment through full deployment, applying established playbooks and executive-level decision-making
- Passing a hands-on technical assessment that validates your capacity to architect and deliver AI-first solutions
What you will NOT be doing
- Overseeing large teams or depending on hierarchical structures to achieve outcomes
- Attending prolonged alignment sessions or waiting for consensus before advancing
- Handing off the complex work to IT departments or outside consultants—you will design and implement the solution directly
- Running steady-state operations—this position centers on transformation and speed
Key responsibilities
Architect and implement AI-first operational systems that remove manual processes, reduce complexity, and enable scalable execution throughout Trilogy's global software portfolio.
Candidate requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years of operational leadership in enterprise software
- 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
- Proven capability to develop automation using Python and integrate with LLM APIs
- Experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable tools
- Track record of moving quickly, thinking autonomously, and delivering high-stakes outcomes without micromanagement
Nice to have
- Background leading large-scale organizational changes such as M&A integrations or mass offboarding
- Track record of architecting and launching AI-driven operational systems
- Collection of automations you have personally developed and deployed at scale
You will be working for
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