Head of Operations, Trilogy; Remote

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

Join to apply for the Head of Operations, Trilogy (Remote) - $200,000/year USD role at Crossover
.

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

$100.00/hr - $100.00/hr

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's the competitive edge we rely on. We move quickly to acquire software companies and scale them at an accelerated pace. Maintaining this momentum requires executives who can architect lean, automated systems rather than add layers of management and personnel.

You will be accountable for complete transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 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, leveraging 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 operates a portfolio of more than 100 products with disciplined efficiency. We work with reduced hierarchy, shorter cycles, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate meaningful impact at scale without navigating bureaucracy or overseeing inflated teams.

Steady‑state operations are not what we do. Transformation is not something we outsource. And we don't bring on people who require permission or extensive teams to produce results. We are seeking a select group of highly technical, execution‑oriented leaders who treat automation as leverage and velocity as a core tactic. If this describes you—you will excel in this environment.

• Driving high‑complexity operational initiatives including M&A integrations, enterprise system migrations, and large‑scale organizational transitions
• Building and launching 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 cut latency
• Owning initiatives end‑to‑end—from analysis to go‑live—leveraging established playbooks and executive‑level decision‑making
• Completing a practical technical assessment to showcase your capability to architect and deliver AI‑first solutions

• Building or managing large teams or depending on multiple layers of personnel to execute
• Spending time in prolonged alignment sessions or waiting for consensus before taking action
• Handing off the complex work to IT departments or third‑party vendors—you will design and build the solution directly
• Running steady‑state operations—this role centers on transformation and speed

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

• 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.)
• Proven ability to write automation in Python and integrate with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to deliver production‑grade automations
• Demonstrated capacity to move quickly, think independently, and produce high‑stakes outcomes without close supervision

• Track record leading large‑scale organizational transitions such as M&A integrations or mass offboarding
• Background in designing and deploying AI‑driven operational systems
• Portfolio of automations you have personally developed and deployed at scale

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things:
Relentlessly…