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

Trilogy; Toronto; Remote; CAD 277,000; Full time

Job summary

A leading software platform company is seeking a Head of Operations to design AI-driven systems and transform operations. This remote role requires over 5 years of operational leadership experience and proficiency in Python automation. Join to drive significant transformations in a growing tech environment, with a compensation of $200,000 annually.

Qualifications

• 5+ years of operational leadership in enterprise software with results.
• 3+ years in customer-facing roles.
• Proven production-grade automation in Python.

Responsibilities

• Design and deploy AI-first operational systems.
• Execute high-stakes operational transformations.
• Build scalable workflows to eliminate manual effort.

Skills

Operational leadership

Customer-facing roles

Python automation

Independent execution

Tools

Cursor

Windsurf

MCP

Job description

Overview

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

Join to apply for the Head of Operations, Trilogy (Remote) role at Trilogy. This role focuses on designing and delivering lean, automated systems to transform acquisitions and portfolio operations.

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 to systematically eliminate manual effort across the organization using tools like Cursor, Windsurf, and MCP.
• Lead mission-critical initiatives from strategic diagnosis to technical implementation using executive judgment and Trilogy playbooks.
• Demonstrate technical capabilities through a hands-on challenge focused on designing and implementing AI-first operational solutions.

What You Won’t Be Doing

• Overseeing large teams or building organizational hierarchies to accomplish objectives.
• Wasting time in consensus-building meetings or navigating bureaucratic approval chains.
• Outsourcing the technical implementation to IT departments or third-party vendors—you\'ll architect and execute solutions directly.
• Maintaining status quo operations—this role exists exclusively to drive transformation and velocity.

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

• 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 with demonstrated results.
• 3+ years in customer-facing roles (Support, Sales, Collections, etc.).
• Proven ability to write production-grade automation in Python and integrate with LLM APIs.
• Hands-on experience using Cursor, Windsurf, MCP, or similar tools to build and deploy automations.
• Demonstrated capacity to execute independently, make high-stakes decisions, and deliver results without supervision.

Nice-to-have Requirements

• Track record leading complex organizational transitions such as M&A integrations or large-scale workforce restructuring.
• Documented success designing and implementing AI-driven operational systems that deliver measurable business outcomes.
• Portfolio of self-built automations deployed at enterprise scale with quantifiable impact metrics.

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. Trilogy is known for seeking top talent, innovating new technology, and incubating new businesses. Our approach emphasizes simple customer-facing designs and scalable cloud-based architectures. Trilogy is a place to 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 www.crossover.com / help-and-faqs for more details on this topic.

Crossover Job Code : LJ-5145-CA-Toronto-HeadofOperatio

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

Referrals increase your chances of interviewing at Trilogy.

J-18808-Ljbffr