This position is for operators who design and redesign scalable systems from the ground up.

Operational excellence is not optional at Trilogy—it's a strategic differentiator. We move quickly to acquire software companies and scale them even faster. Keeping pace demands leaders who build lean, automated systems rather than adding layers of people to manage complexity.

You will take ownership of complete transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 1,200 employees after an acquisition, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of manual hours. You'll work rapidly with Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep you focused on results.

Trilogy manages a portfolio of 100+ products with disciplined efficiency. We function with minimal hierarchy, compressed timelines, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or leading oversized teams.

We do not maintain static operations. We do not delegate transformation to third parties. And we do not hire individuals who require approval or large teams to execute. We are seeking a select group of technically sophisticated, execution-driven leaders who treat automation as a force multiplier and speed as a core tactic. If this describes you—this environment will suit you well.

What You Will Be Doing

• Delivering high-complexity operational initiatives including M&A integrations, enterprise platform migrations, and large-scale organizational shifts
• Building and launching automations that replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-enabled workflows with Cursor, Windsurf, and MCP to remove manual processes and cut cycle time
• Driving projects end-to-end—from initial assessment to final deployment—leveraging established playbooks and executive-level decision-making
• Completing a practical technical assessment to validate your capability to design and deliver AI-first solutions

What You Won’t Be Doing

• Building or depending on large teams to accomplish objectives
• Attending prolonged alignment sessions or waiting for consensus before taking action
• Handing off the complex work to IT departments or outside consultants—you will design and implement solutions directly
• Running steady-state operations—this position centers on transformation and rapid execution

AI Operations Specialist Key Responsibilities

Architect and implement AI-first operational platforms that remove manual work, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.

Basic 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 write automation in Python and integrate with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to deliver production-grade automations
• Demonstrated ability to execute quickly, think autonomously, and produce high-stakes outcomes without supervision

Nice-to-have Requirements

• Track record leading large-scale organizational changes such as M&A integrations or mass offboarding
• Background in designing and launching AI-driven operational systems
• Collection of automations you have personally developed and deployed at scale

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs.

Disclaimer: This job description has been formatted by AI for readability. Please verify all details with the employer before applying.