Crossover Hiring – AI Operations Specialist (Trilogy) | $200,000/Year USD | Remote | Apply Now

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🧑‍💼 About the Company – Trilogy (via Crossover)

Trilogy is one of the world’s most respected software groups, running a portfolio of 100+ global software products. They operate with:

  • High performance

  • Lean structures

  • Automated workflows

  • Rapid acquisition & transformation cycles

For 30+ years, Trilogy has been known for:
✔ Hiring top 1% global talent
✔ Innovation in cloud & enterprise engineering
✔ Large-scale business transformation
✔ AI-driven operations

Hiring is managed through Crossover, known for premium remote global roles with industry-leading compensation.

📌 Job Summary

💼 Role AI Operations Specialist
🏢 Company Trilogy (via Crossover)
📍 Location Remote (US/Canada/LatAm/Western Europe – UTC -8 to UTC +2)
💰 Salary $100/hr • $200,000/year USD
🕒 Work Type Full-Time • 40 hrs/week

🧠 About the Role – AI Operations Specialist

This role is designed for deeply technical operators who can architect AI-powered systems to replace manual workflows at scale.

You will not be maintaining steady-state operations.
You will always be building, transforming, and automating processes across Trilogy’s global portfolio.

This position directly impacts how enterprise systems—HR, CRM, task management, support, sales and internal workflows—run across 100+ companies.


🔍 Key Responsibilities

🚀 You will be doing:

✔ Leading high-complexity operational transformations
✔ Executing M&A integration workflows (e.g., offboarding 1,200+ employees)
✔ Replacing CRMs like Salesforce/Jira with AI agent workflows
✔ Building Python-based automations integrated with LLM APIs
✔ Using tools like:

  • Cursor

  • Windsurf

  • MCP
    ✔ Owning end-to-end execution from strategy → design → deployment
    ✔ Leveraging Trilogy’s transformation playbooks
    ✔ Passing a hands-on technical assessment validating AI automation skills

❌ You will NOT be doing:

✘ Managing large teams or relying on multiple layers of hierarchy
✘ Spending hours in alignment meetings
✘ Delegating technical work to IT or external vendors
✘ Running routine or repetitive operations

This is a pure transformation, automation, and execution role.

🎯 Key Responsibility Summary

Architect and implement AI-first systems that eliminate manual work, reduce complexity, and scale enterprise operations across Trilogy’s global software ecosystem.

🎓 Eligibility & Requirements

✅ Basic Requirements

  • Must live in:
    US, Canada (excluding California), South America, Central America, Western Europe
    (UTC -8 to UTC +2)

  • 5+ years experience in enterprise operational leadership

  • 3+ years customer-facing role experience

  • Strong Python automation experience

  • Ability to integrate with LLM APIs

  • Experience with Cursor, Windsurf, MCP or similar

  • Proven independent problem solver who delivers high-stakes outcomes quickly

  • High technical literacy across enterprise systems

⭐ Nice-to-Have Qualifications

  • Past experience handling large-scale:
    ✔ M&A transitions
    ✔ Mass offboarding
    ✔ Organizational migrations

  • Experience designing AI-driven enterprise workflows

  • Portfolio of Python automations demonstrating scale and complexity

🎁 What Trilogy Offers

  • $200,000/year USD

  • Weekly payments via Crossover

  • 100% remote global work

  • High ownership, zero bureaucracy

  • Work directly on large-scale AI transformations

  • Opportunity to influence enterprise-wide operations

📅 Work Details

  • Full-time (40 hours/week)

  • Long-term contractor role

  • Contractor agreement required

  • Immediate start available

📩 How to Apply

👉 Click the "Apply / Click Here" button on our blog.
You will be redirected to the official Crossover application page.

Direct Link to Apply

Assessment includes:

  • Technical automation tasks

  • AI-first problem-solving challenges

  • Python + LLM workflows evaluation

Only shortlisted applicants will be contacted.

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