Operations AI Lead, Trilogy (Remote) - $200,000/year USD

This position is designed for operators who know how to architect and re-architect systems built for scale.

Operational excellence at Trilogy isn't optional—it's the competitive edge. Our model involves acquiring software companies rapidly and scaling them even more rapidly. Sustaining that pace requires executives capable of engineering lean, automated systems rather than absorbing complexity through hiring.

You'll take ownership of complete transformations across our global portfolio. Examples include redesigning offboarding processes for 1,200+ employees following acquisitions, replacing platforms like Jira and Salesforce with AI agent architectures, or deploying automations that save thousands of manual hours. Execution happens quickly using 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 disciplined efficiency. We maintain fewer organizational layers, shorter cycle times, and higher performance standards than conventional enterprise settings. This role offers the opportunity to generate impact at scale without navigating bureaucracy or overseeing inflated teams.

We don't operate in steady-state mode. We don't farm out transformation work. And we don't bring on people who require approval chains or large teams to deliver. We're seeking a select group of deeply technical, execution-oriented leaders who treat automation as leverage and speed as core strategy. If that describes you—this is where you'll excel.

What You Will Be Doing

• Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Architecting and delivering automations that replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
• Owning initiatives end-to-end—from diagnostic phase through deployment—using established playbooks and executive judgment
• Undertaking a hands-on technical assessment to validate your capability to design and build AI-first solutions
  
  

What You Won’t Be Doing

• Overseeing large teams or depending on organizational layers to accomplish objectives
• Attending endless coordination meetings or waiting for consensus before taking action
• Handing off the complex work to IT departments or outside vendors—you'll design and build the solution directly
• Running steady-state operations—this role centers on transformation and speed
  
  

Operations AI Lead Key Responsibilities

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

Basic Requirements

• Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
• 5+ years of operational leadership within enterprise software
• 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
• Proven capability to develop automation in Python and integrate with LLM APIs
• Hands-on experience using Cursor, Windsurf, MCP, or comparable tools to deliver production-grade automations
• Track record of moving quickly, thinking autonomously, and delivering high-stakes outcomes without supervision
  
  

Nice-to-have Requirements

• Background leading large-scale organizational transitions including M&A integrations or mass offboarding
• Track record of architecting and deploying AI-driven operational systems
• Collection of automations you've personally designed and shipped at scale
  
  

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5145-PH-Manila-OperationsAILe