Head of Operations
$200,000 USD/year ^{Pay is set based on global value, not the local market.

Most roles = hourly rate x 40 hrs x 50 weeks}($100 USD/hour)

Head of Operations $200,000 USD/year ($100 USD/hour)

Fully-remote

Description

This position is designed for operators capable of designing and redesigning systems built to scale.

Operational excellence at Trilogy is not optional—it is our competitive edge. We move quickly to acquire software companies and scale them even more rapidly. Sustaining this pace requires executives who can architect lean, automated systems rather than relying on headcount to absorb complexity.

You will take ownership of complete operational transformations spanning our global portfolio. Examples include restructuring the offboarding process for 1,200+ employees following acquisitions, replacing platforms like Jira and Salesforce with AI-driven agents, or deploying automations that remove thousands of hours of manual effort. Execution will be rapid, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that allow you to concentrate on results.

Trilogy operates a portfolio of 100+ products with disciplined efficiency. We maintain fewer organizational layers, shorter cycle times, and more demanding standards than conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or managing oversized teams.

Steady-state operations are not part of our model. We do not outsource transformation. We do not hire individuals who require extensive permission structures or large teams to deliver results. We are seeking a limited number of highly technical, execution-focused leaders who treat automation as leverage and speed as core strategy. If this describes you—this environment will suit you well.

What you will be doing

Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
Building and deploying automations to replace CRM and task management platforms using Python and LLM APIs
Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and shorten execution cycles
Owning initiatives end-to-end—from diagnosis through deployment—applying proven playbooks and executive-level decision-making
Completing a practical technical assessment to validate your capability to architect and deliver AI-first solutions

What you will NOT be doing

Building or managing large teams or depending on multiple reporting layers to achieve outcomes
Participating in prolonged alignment sessions or waiting for consensus before taking action
Handing off complex work to IT departments or third-party vendors—you will design and execute the solution directly
Operating in a steady-state maintenance capacity—this role centers on transformation and speed

Key responsibilities

Architect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.

Candidate requirements

5+ years of operational leadership in business operations
Experience making presentations to C-suite executives
Experience writing automation in Python and integrate with LLM APIs
Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
Remote work capability with at least 6 hours of overlap with the CST time zone

How it works

CROSSOVER'S PROCESS

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