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

TrilogyMadrid, Comunidad de Madrid, España

Hace 12 días

Descripción del trabajo

Overview

Trilogy Madrid, Community of Madrid, Spain

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 eliminate manual effort across the organization
Lead mission-critical initiatives from strategic diagnosis to technical implementation using executive judgment and Trilogy\'s 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 technology, and incubating new businesses. The focus is on simple customer-facing designs and rapid growth, with opportunities to develop your career.

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. Compensation is $100 USD / hour, equivalent to $200,000 USD / year assuming 40 hours per week and 50 weeks per year. Payment is weekly. For details, see

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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Head Of • Madrid, Comunidad de Madrid, España