Head of Operations, Trilogy

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

Join to apply for the Head of Operations, Trilogy (Remote) - $200,000/year USD role at Trilogy

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

Overview

ELITE OPERATORS WANTED: Build the Systems That Outperform the Industry. At Trilogy, operational excellence isn’t a nice-to-have; it’s our unfair advantage. We acquire software companies fast, and we scale them even faster. To keep up, we need executives who can design and deliver lean, automated systems—not manage complexity with headcount. 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. If that’s you—you’ll thrive here.

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

• 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 has been known for relentlessly seeking top talent, innovating new technology, and incubating new businesses. Our focus is on simple customer-facing designs and scalable cloud-based stacks. 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. See for details.

Crossover Job Code: LJ-5145-BR-SãoPaulo-HeadofOperatio

Seniority level

• Director

Employment type

• Full-time

Job function

• Management, Engineering, and Strategy/Planning

Industries

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

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