Head of Operations, Trilogy (Remote) - $200,000 / year USD

Head of Operations, Trilogy (Remote) - $200,000 / year USD

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Overview

This is a full-time, remote, senior operational leadership role focused on end-to-end transformations across Trilogy's global software portfolio. You will design and deliver lean, automated systems to replace traditional manual processes and drive rapid, measurable impact.

What You Will Be Doing

• Execute high-stakes operational transformations including M&A integrations, enterprise system migrations, and organizational restructures with measurable business impact
• Design and deploy AI-powered automations that replace traditional CRM and task management systems using Python and advanced LLM APIs
• Build scalable workflows via Cursor, Windsurf, and MCP that systematically eliminate manual effort across the organization
• Lead mission-critical initiatives from strategic diagnosis to technical implementation using executive judgment and Trilogy's battle-tested playbooks
• Demonstrate your technical capabilities through a hands-on challenge focused on designing and implementing AI-first operational solutions

What You Won’t Be Doing

Head Of Operations 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

Nice-to-have Requirements

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

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. Consult for more details on this topic.

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