Description
This position is designed for operators capable of constructing and reconstructing scalable systems from the ground up.
Operational excellence at Trilogy isn't merely aspirational—it represents our competitive edge. Our acquisition velocity for software companies is aggressive, and our scaling pace exceeds it. Sustaining this momentum requires executives who architect lean, automated infrastructure rather than address complexity through workforce expansion.
You will assume ownership of complete transformations spanning our international portfolio. This might involve redesigning offboarding procedures for 1,200+ employees following acquisitions, substituting Jira and Salesforce with AI-driven agents, or constructing automation frameworks that remove thousands of manual labor hours. Execution will be rapid, leveraging Python, LLM APIs, platforms such as Cursor, Windsurf, and MCP—supported by battle-tested playbooks that keep your focus on deliverables.
Trilogy manages a portfolio exceeding 100 products with uncompromising efficiency. We function with reduced hierarchies, accelerated iteration cycles, and elevated performance standards compared to conventional enterprise settings. This opportunity enables you to generate large-scale impact without navigating bureaucratic obstacles or supervising oversized teams.
Steady-state operations are not our domain. We do not delegate transformation externally. And we do not recruit individuals requiring authorization or extensive teams to produce results. Our search targets a select group of deeply technical, execution-oriented leaders who treat automation as force multiplication and velocity as strategic doctrine. If this describes your approach—you will excel in this environment.
What you will be doing
- Delivering high-complexity operational initiatives including M&A integration work, enterprise-scale system migrations, and organization-wide structural transitions
- Architecting and launching automation solutions that supplant CRM and task orchestration platforms through Python and LLM API implementation
- Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to eradicate manual processes and minimize operational latency
- Driving projects from initial assessment through full deployment, applying established playbooks and executive-caliber decision-making
- Executing a practical technical assessment to validate your capability in designing and building AI-centric solutions
What you will NOT be doing
- Overseeing large teams or depending on organizational layers to achieve execution
- Participating in prolonged alignment sessions or waiting for consensus before advancing
- Assigning core technical work to IT departments or third-party vendors—you will design and build the solution directly
- Operating in maintenance mode—this position centers on continuous transformation and execution speed
Key responsibilities
Architect and implement AI-centric operational frameworks that remove manual intervention, reduce system complexity, and enable scalable execution throughout Trilogy's worldwide software holdings.
Candidate requirements
- Located in North America (California excluded), South/Central America, or Western Europe (UTC -8 through UTC +2)
- 5+ years leading operations within enterprise software environments
- 3+ years in client-facing functions (Support, Sales, Collections, or equivalent)
- Verified capability to develop automation using Python and interface with LLM APIs
- Hands-on experience deploying production-ready automations with Cursor, Windsurf, MCP, or comparable platforms
- Documented track record of rapid execution, autonomous problem-solving, and delivering critical outcomes without continuous oversight
Nice to have
- Background leading enterprise-scale organizational transformations including M&A integration or large-scale workforce transitions
- Track record designing and launching AI-powered operational infrastructure
- Catalog of automation solutions you have independently developed and deployed at scale
You will be working for
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