Director of Operational Excellence
$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 scalable systems from the ground up.

Operational excellence at Trilogy is not optional—it is the foundation of our competitive edge. We move quickly to acquire software companies and scale them even faster. To sustain this pace, we require executives who can architect lean, automated infrastructures—not expand complexity through additional headcount.

You will take ownership of comprehensive transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI-driven agents, or creating automation solutions that remove thousands of manual hours from operations. 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 keep your focus on results.

Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We maintain fewer hierarchical layers, accelerated decision cycles, and elevated performance standards compared to conventional enterprise settings. This is an opportunity to generate large-scale impact without navigating bureaucracy or supervising oversized teams.

Steady-state operations are not our model. Transformation is never outsourced. We do not hire individuals who require approval or extensive teams to produce results. We seek a select group of deeply technical, execution-oriented 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

Leading high-complexity operational initiatives including M&A integrations, enterprise-scale system migrations, and large organizational transitions
Building and deploying automations that replace CRM and task management platforms through Python and LLM API integration
Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and decrease cycle time
Driving projects from initial diagnosis through final deployment, applying established playbooks and executive judgment
Participating in a practical technical assessment to validate your capability to design and execute AI-first solutions

What you will NOT be doing

Overseeing large teams or depending on multiple organizational layers to achieve outcomes
Spending time in prolonged alignment sessions or waiting for consensus before taking action
Handing off difficult work to IT departments or third-party vendors—you will design and implement solutions directly
Operating in steady-state maintenance mode—this role is centered on transformation and rapid execution

Key responsibilities

Architect and implement AI-first operational infrastructures 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 delivering presentations to C-suite executives
Experience developing automation using Python and integrating with LLM APIs
Experience utilizing Cursor, Windsurf, MCP, or comparable tools to deliver production-grade automations
Remote work capability with a minimum of 6 hours of overlap with the CST time zone

How it works

CROSSOVER'S PROCESS

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