Overview
Head of Operations, Trilogy (Remote) - $200,000/year USD
Base pay range: $100.00/hr - $100.00/hr
ELITE OPERATORS WANTED: Build the Systems That Outperform the Industry. At Trilogy, operational excellence isn't a nice-to-have; it's our unfair advantage. We acquire software companies fast, and we scale them even faster. To keep up, we need executives who can design and deliver lean, automated systems—not manage complexity with headcount.
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 battle-tested 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
- Wasting time in consensus-building meetings or navigating 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 exclusively to drive transformation and velocity
Head Of Operations Key Responsibilities
Design and deploy AI-first operational systems that eliminate manual effort, compress 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 is known for seeking top talent, innovating new technology, and incubating new businesses. Our approach centers on customer-facing design and scalable cloud-based stack growth. Trilogy is a place to grow your career with great people and meaningful work.
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. For details, see www.crossover.com/help-and-faqs.
Crossover Job Code: LJ-5145-US-Seattle-HeadofOperatio
Seniority level
Employment type
Job function
- Management
- Engineering
- Strategy/Planning
Industries
- Software Development
- IT Services and IT Consulting
- Technology, Information and Internet
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