Description
This role is for operators who can build and rebuild systems that scale.
At Trilogy, operational excellence isn’t a nice-to-have; it’s our unfair advantage. We acquire software companies fast, and we scale them even faster. To keep up, we need executives who can design and deliver lean, automated systems—not manage complexity with headcount.
In this role, you’ll own end-to-end transformations across our global portfolio. That could mean reworking how we offboard 1,200+ employees post-acquisition, replacing Jira and Salesforce with AI agents, or building automations that eliminate thousands of manual hours. You’ll execute fast using Python, LLM APIs, tools like Cursor, Windsurf, and MCP—and a stack of proven playbooks that let you focus on outcomes.
Trilogy runs a 100+ product portfolio with ruthless efficiency. We operate with fewer layers, faster cycles, and higher expectations than traditional enterprise environments. This is your chance to drive impact at scale without battling bureaucracy or managing bloated teams.
We don’t do steady-state ops. We don’t outsource transformation. And we don’t hire people who need permission or a big team to deliver. We’re looking for a small number of deeply technical, execution-first leaders who use automation as leverage and speed as strategy. If that’s you—you’ll thrive here.
What you will be doing
- Executing high-complexity operational projects such as M&A integrations, enterprise system migrations, and large-scale org transitions
- Designing and shipping automations that replace CRM and task management tools using Python and LLM APIs
- Deploying AI-powered workflows via Cursor, Windsurf, and MCP to eliminate manual work and reduce latency
- Leading initiatives from diagnosis to deployment, using proven playbooks and executive-level judgment
What you will NOT be doing
- Managing large teams or relying on layers of people to get things done
- Sitting through endless alignment meetings or relying on consensus to move
- Delegating the hard work to IT or external vendors—you’ll architect and execute the solution yourself
- Maintaining steady-state operations—this role is built around transformation and velocity
Key responsibilities
Design and deploy AI-first operational systems that eliminate manual effort, compress complexity, and drive scalable execution across Trilogy’s global software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience making presentations to C-suite executives
- Experience writing automation in Python and integrate with LLM APIs
- Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
- Remote work capability with at least 6 hours of overlap with the CST time zone
You will be working for
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