Head of Operations, Trilogy (Remote) - $200,000/year USD

Head of Operations, Trilogy (Remote) - $200,000/year USD

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This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more.

Base pay range

$100.00/hr – $100.00/hr

This position is designed for operators capable of building and restructuring systems that scale effectively. Operational excellence at Trilogy is not optional—it is a core competitive advantage. We acquire software businesses rapidly and accelerate their growth even faster. Sustaining this pace requires executives who can architect and implement lean, automated systems rather than managing complexity through additional personnel. You will take ownership of comprehensive transformations across our global portfolio, including redesigning offboarding processes, replacing platforms, and creating automations that remove thousands of manual hours. Execution will be rapid, using Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of proven playbooks that allow you to concentrate on results. Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We function with minimal hierarchy, accelerated timelines, and higher performance standards than conventional enterprise settings. This role offers the opportunity to generate significant impact at scale without navigating bureaucracy or overseeing large teams.

What You Will Be Doing

• Executing operationally complex projects 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
• Driving initiatives from problem diagnosis through deployment, applying proven playbooks and executive-level decision-making
• Completing a hands‑on technical assessment to validate your capability to design and deploy AI‑first solutions

What You Won’t Be Doing

• Building or managing large teams or depending on hierarchical structures to execute
• Participating in prolonged alignment sessions or waiting for consensus to proceed
• Handing off the complex technical work to IT departments or external contractors—you will design and implement the solution directly
• Operating in maintenance mode—this role centers on transformation and speed of execution

Key Responsibilities

Architect and implement AI-first operational systems that remove manual effort, 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 in enterprise software
• 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
• Demonstrated ability to write automation in Python and integrate with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
• Proven ability to move fast, think independently, and deliver high‑stakes results without handholding

Nice‑to‑have Requirements

• Experience leading large-scale organizational transitions such as M&A integrations or mass offboarding
• History of designing and deploying AI-driven operational systems
• Portfolio of automations you personally built 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.

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 for more details on this topic.

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