Overview

Operations AI Lead, Trilogy (Remote) - $200,000/year USD

This role focuses on building scalable, AI-driven operational systems within Trilogy’s portfolio. The role emphasizes transformation and automation over adding headcount and avoids large teams or multi-layer approvals.

What You Will Be Doing

• Implementing complex operational projects, including mergers and acquisitions integrations, enterprise system migrations, and extensive organizational transitions
• Creating and deploying automations to replace CRM and task management tools using Python and LLM APIs
• Launching AI-driven workflows through tools like Cursor, Windsurf, and MCP to minimize manual labor and increase efficiency
• Leading initiatives from concept to implementation, guided by proven playbooks and high‑level decision‑making
• Completing a practical technical challenge to showcase your expertise in designing and implementing AI-centric solutions

What You Won’t Be Doing

• Overseeing large teams or relying on multiple layers of personnel to accomplish tasks
• Enduring endless alignment meetings or depending on consensus for progress
• Delegating challenging tasks to IT or vendors—you will design and implement the solutions yourself
• Maintaining routine operations—this role focuses on transformation and rapid progress

Operations AI Lead Key Responsibilities

Craft and implement AI-centric operational systems that eradicate manual tasks, simplify complexity, and enable scalable execution across Trilogy’s software portfolio.

Basic Requirements

• Reside in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
• 5+ years of leadership experience in enterprise software operations
• 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
• Proven expertise in writing automation scripts in Python and integrating with LLM APIs
• Experience with tools like Cursor, Windsurf, MCP, or similar for delivering production-ready automations
• Demonstrated capability to act swiftly, think independently, and achieve high-impact results without guidance

Nice-to-have Requirements

• Experience in managing large-scale organizational changes such as mergers and acquisitions or mass offboarding
• A track record of designing and deploying AI-powered operational systems
• A portfolio showcasing automations you have personally developed and implemented at scale

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. Trilogy is known for relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our focus is on simple, customer-facing designs and rapidly scaling innovative ideas.

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. For details, see www.crossover.com/help-and-faqs.

Crossover Job Code: LJ-5145-GB-London-OperationsAILe

Seniority level

• Director

Employment type

• Full-time

Job function

• Management
• Engineering
• Strategy/Planning

Industries

• Software Development
• IT Services and IT Consulting
• Technology, Information and Internet