AI Operations Specialist
$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 built for scale.

Operational excellence at Trilogy is not optional—it is our competitive edge. We move quickly to acquire software companies and scale them at an accelerated pace. To sustain this momentum, we require leaders who can architect and implement efficient, automated systems rather than expand headcount to absorb complexity.

You'll be accountable for complete transformations spanning our worldwide portfolio. This might involve redesigning the offboarding process for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI-powered agents, or creating 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 established playbooks that enable a focus on results.

Trilogy operates a portfolio exceeding 100 products with disciplined efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This presents an opportunity to generate large-scale impact without navigating bureaucracy or overseeing oversized teams.

Steady-state operations are not our model. We keep transformation in-house. And we do not recruit individuals who require authorization or extensive resources to produce results. We seek a select group of highly technical, execution-oriented leaders who treat automation as leverage and speed as core strategy. If this describes you—you will excel here.

What you will be doing

Delivering complex operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
Building and deploying automations using Python and LLM APIs to replace CRM and task management platforms
Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual tasks and decrease response time
Driving projects from initial assessment to final deployment, applying proven playbooks and executive-level decision-making
Passing a practical technical assessment to verify your capability to architect and deliver AI-first solutions

What you will NOT be doing

Building or managing large teams or depending on multiple layers to execute
Attending prolonged alignment sessions or waiting for consensus to advance
Assigning the complex work to IT departments or third-party vendors—you will design and build the solution 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 tasks, reduce complexity, and enable scalable execution throughout Trilogy's international 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 comparable tools
Ability to work remotely with a minimum of 6 hours overlap with the CST time zone

How it works

CROSSOVER'S PROCESS

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Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.