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

Overview

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

Trilogy provided pay range. This range is provided by Trilogy. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range: $100.00/hr - $100.00/hr

What You Will Be Doing

In this role, you'll own end-to-end transformations across our global portfolio. This could include 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.

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
• Completing a hands-on technical challenge to demonstrate your ability to design and implement AI-first solutions

What You Won’t 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

Operations AI Innovator 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.

Basic Requirements

• Based 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.)
• Demonstrated ability to write automation in Python and integrate with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
• Proven ability to move fast, think independently, and deliver high-stakes results without handholding

Nice-to-have Requirements

• Experience leading large-scale organizational transitions such as M&A integrations or mass offboarding
• History of designing and deploying AI-driven operational systems
• Portfolio of automations you\'ve personally built and shipped at scale

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for relentingly seeking top talent, innovating new technology, and incubating new businesses. Our focus is simple customer-facing design and rapid growth of new ventures on a modern cloud-based stack.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

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-IT-COUNTRY-OperationsAIIn

Seniority level

• Director

Employment type

• Full-time

Job function

• Management, Engineering, and Strategy/Planning

Industries

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

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