Description
Are you a systems architect who thrives in high-velocity environments, crafting solutions that redefine efficiency?
At Trilogy, operational mastery is our secret weapon. We rapidly acquire and scale software companies, demanding executives who can engineer streamlined, automated systems—not merely manage complexity via manpower.
In this pivotal role, you'll drive comprehensive transformations across our global portfolio. Whether it's streamlining the offboarding of 1,200+ employees post-acquisition, replacing Jira and Salesforce with AI-driven solutions, or creating automations that save thousands of manual hours, you'll be executing with speed using Python, LLM APIs, and tools like Cursor, Windsurf, and MCP—backed by a suite of proven playbooks focused on results.
Trilogy operates a vast 100+ product portfolio with unmatched efficiency. We cut through layers, accelerate cycles, and set higher benchmarks than traditional enterprises. This is your opportunity to make a large-scale impact without the hindrance of bureaucracy or oversized teams.
We eschew steady-state operations, outsourcing transformations, and hiring those who need teams or permission to perform. We seek a select few deeply technical, execution-driven leaders who wield automation as a tool and speed as their strategy. If this resonates with you, you'll excel in our environment.
What you will be doing
- Executing complex operational projects like M&A integrations, enterprise system migrations, and large-scale organizational transitions
- Designing and implementing automations that replace CRM and task management tools using Python and LLM APIs
- Deploying AI-powered workflows with tools like Cursor, Windsurf, and MCP to eliminate manual tasks and reduce latency
- Leading projects from diagnosis through to deployment, applying proven playbooks and executive-level decision-making
- Tackling a hands-on technical challenge to showcase your capability in creating AI-first solutions
What you will NOT be doing
- Managing large teams or depending on multiple layers of personnel to achieve objectives
- Participating in endless alignment meetings or requiring consensus to make progress
- Delegating challenging tasks to IT or external vendors—you'll be responsible for architecting and executing solutions
- Maintaining steady-state operations—this role is centered on transformation and rapid execution
Key responsibilities
Candidate requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years in operational leadership within enterprise software
- 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
- Proven proficiency in writing automation scripts in Python and integrating with LLM APIs
- Experience utilizing Cursor, Windsurf, MCP, or similar tools to deliver production-grade automations
- Demonstrated ability to act swiftly, think autonomously, and achieve significant results without supervision
Nice to have
- Experience in leading large-scale organizational changes such as M&A integrations or mass offboarding
- Track record of designing and deploying AI-driven operational systems
- Portfolio showcasing automations you've developed and deployed at scale
You will be working for
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