Description
This position is built for operators capable of architecting and re-architecting systems at scale.
Operational excellence at Trilogy isn't optional—it's the competitive edge that sets us apart. We acquire software companies at speed and scale them even faster. Sustaining that momentum requires executives who can architect lean, automated systems rather than layering in complexity through headcount.
You'll take ownership of complete transformations spanning our global portfolio. This might involve reimagining the offboarding process for 1,200+ employees following an acquisition, replacing platforms like Jira and Salesforce with AI-driven agents, or creating automations that remove thousands of manual hours from workflows. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—alongside a library of battle-tested playbooks that keep you focused squarely on results.
Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We function with fewer hierarchies, shorter cycles, and steeper expectations than conventional enterprise settings. This represents an opportunity to generate impact at scale without navigating bureaucracy or overseeing inflated teams.
Steady-state operations aren't our model. We don't delegate transformation externally. And we don't bring on people who require approval or extensive teams to produce outcomes. We're seeking a limited number of deeply technical, execution-oriented 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-stakes operational initiatives including M&A integrations, enterprise platform migrations, and large-scale organizational transitions
- Building and delivering automations that supplant CRM and task management systems, using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and cut latency
- Driving projects from initial assessment through full deployment, applying proven playbooks and executive-caliber decision-making
- Working through a practical technical assessment to validate your capability in designing and shipping AI-first solutions
What you will NOT be doing
- Building or overseeing large teams or depending on multiple organizational layers to achieve results
- Attending prolonged alignment sessions or waiting for consensus before taking action
- Handing off the complex work to IT departments or third-party vendors—you'll design and implement the solution directly
- Running steady-state operations—this role centers on transformation and speed
Key responsibilities
Architect and implement AI-first operational frameworks that remove manual work, reduce complexity, and enable scalable execution throughout Trilogy's global software portfolio.
Candidate requirements
- Located in North America (California excluded), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years leading operations in enterprise software environments
- 3+ years working in customer-facing functions (Support, Sales, Collections, etc.)
- Proven ability to develop automation using Python and integrate LLM APIs
- Hands-on experience with Cursor, Windsurf, MCP, or comparable tools to deliver production-ready automations
- Established track record of moving quickly, thinking autonomously, and delivering critical results without supervision
Nice to have
- Background leading major organizational changes such as M&A integrations or large-scale offboarding
- Track record designing and launching AI-powered operational systems
- Collection of automations you've independently developed and deployed at scale
You will be working for
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