Operations AI Innovator
$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 defines our competitive edge. We acquire software companies rapidly and scale them with even greater speed. Sustaining this momentum requires executives who design and implement lean, automated systems rather than address complexity through additional headcount.

You will take ownership of complete transformations spanning our global portfolio. This might include redesigning the offboarding process for 1,200+ employees following an acquisition, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of hours of manual effort. Execution will be rapid, utilizing Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep you focused on results.

Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We function with reduced organizational layers, accelerated cycles, and elevated expectations compared to conventional enterprise settings. This represents an opportunity to generate large-scale impact without navigating bureaucracy or overseeing oversized teams.

Steady-state operations are not our model. Transformation is never outsourced. And we do not hire individuals who require permission or extensive teams to deliver results. We are seeking a limited number of deeply technical, execution-oriented leaders who leverage automation and treat speed as a strategic asset. If this describes you—this environment will suit you well.

What you will be doing

Executing operationally complex projects including M&A integrations, enterprise system migrations, and organization-wide transitions
Architecting and delivering automations that supplant CRM and task management platforms using Python and LLM APIs
Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
Driving initiatives from initial diagnosis through to deployment, applying proven playbooks and executive-level decision-making
Completing a practical technical challenge that validates your capacity to design and build AI-first solutions

What you will NOT be doing

Leading large teams or depending on multiple organizational layers to accomplish objectives
Attending protracted alignment sessions or waiting for consensus before acting
Passing the technical 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 speed

Key responsibilities

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

Candidate requirements

5+ years of operational leadership in business operations
Experience presenting 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 at least 6 hours of overlap with the CST time zone

How it works

CROSSOVER'S PROCESS

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