Head of Operations, Trilogy (Remote) - $200,000/year USD
This is a full-time, remote leadership role overseeing end-to-end operational transformations across Trilogy's global software portfolio. The compensation listed reflects a base rate; final pay will be discussed with the recruiter.
What You Will Be Doing
Execute high-stakes operational transformations including M&A integrations, enterprise system migrations, and organizational restructures with measurable business impact
Design and deploy AI-powered automations that replace traditional CRM and task management systems using Python and advanced LLM APIs
Build scalable workflows via Cursor, Windsurf, and MCP that systematically eliminate manual effort across the organization
Lead mission-critical initiatives from strategic diagnosis to technical implementation using executive judgment and Trilogy's playbooks
Demonstrate your technical capabilities through a hands-on challenge focused on designing and implementing AI-first operational solutions
What You Won’t Be Doing
Overseeing large teams or building organizational hierarchies to accomplish objectives
Participating in lengthy consensus-building meetings or bureaucratic approval chains
Outsourcing the technical implementation to IT departments or third-party vendors—you’ll architect and execute solutions directly
Maintaining status quo operations—this role exists to drive transformation and velocity
Head Of Operations Key Responsibilities
Design and deploy AI-first operational systems that eliminate manual effort, reduce complexity, and drive scalable execution across Trilogy's global software portfolio.
Basic Requirements
Based in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
5+ years of operational leadership in enterprise software with demonstrated results
3+ years in customer-facing roles (Support, Sales, Collections, etc.)
Proven ability to write production-grade automation in Python and integrate with LLM APIs
Hands-on experience using Cursor, Windsurf, MCP, or similar tools to build and deploy automations
Demonstrated capacity to execute independently, make high-stakes decisions, and deliver results without supervision
Nice-to-have Requirements
Track record leading complex organizational transitions such as M&A integrations or large-scale workforce restructuring
Documented success designing and implementing AI-driven operational systems that deliver measurable business outcomes
Portfolio of self-built automations deployed at enterprise scale with quantifiable impact metrics
About Trilogy
Hundreds of software businesses run on the Trilogy Business Platform. Trilogy values top talent, technological innovation, and incubation of new ideas. The company emphasizes simple customer-facing designs and scalable cloud-based stack growth. Trilogy offers opportunities to grow your career and work with a collaborative team.
Working with Us
This is a full-time (40 hours per week), long-term position. It requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level is $100 USD/hour, equating to $200,000 USD/year with standard work terms. The payment period is weekly. For more details, consult crossover.com help and FAQs.
Job Details
Seniority level: Director
Employment type: Full-time
Job function: Management, Engineering, and Strategy/Planning
Industries: Software Development, IT Services and IT Consulting, Technology, Information and Internet
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