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)

Not accepting applications on crossover.com at this time.

Description

This position is designed for operators capable of constructing and reconstructing systems at scale.

Operational excellence at Trilogy is not optional—it is the foundation of our competitive edge. We acquire software companies rapidly and scale them with even greater speed. Sustaining this requires executives who can architect lean, automated systems rather than add complexity through headcount expansion.

You will take ownership of complete transformations across our global portfolio. This might include redesigning the offboarding process for 1,200+ employees following an acquisition, replacing legacy platforms like Jira and Salesforce with AI-driven agents, or creating automations that remove thousands of manual hours from workflows. Execution will be fast, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of tested playbooks that enable you to concentrate on results.

Trilogy operates a portfolio of over 100 products with uncompromising efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This opportunity allows you to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.

Steady-state operations are not part of our model. Transformation is not outsourced. We do not recruit individuals who require approval or extensive teams to produce results. Our search is for a select group of deeply technical, execution-oriented leaders who treat automation as leverage and speed as a core strategy. If this describes you, you will excel in this environment.

What you will be doing

Executing high-stakes operational projects including M&A integrations, enterprise system migrations, and organization-wide transitions
Architecting and delivering automations that supplant CRM and task management platforms through Python and LLM APIs
Implementing AI-driven workflows using Cursor, Windsurf, and MCP to remove manual processes and decrease latency
Directing initiatives from initial assessment through deployment, applying established playbooks and executive judgment
Successfully completing a practical technical challenge that validates your capacity to design and build AI-first solutions

What you will NOT be doing

Overseeing large teams or depending on multiple organizational layers to achieve outcomes
Participating in protracted alignment sessions or waiting for consensus before acting
Handing off the complex work to IT departments or third-party vendors—you will design and execute solutions directly
Running steady-state operations—this position centers on transformation and rapid execution

Key responsibilities

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

Candidate requirements

5+ years of operational leadership in business operations
Experience delivering presentations to C-suite executives
Experience building automation in Python and integrating with LLM APIs
Experience deploying production-grade automations using Cursor, Windsurf, MCP, or similar tools
Remote work capability with a minimum of 6 hours overlap with the CST time zone

How it works

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