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

What You Will Be Doing

• Delivering high-stakes operational initiatives including M&A integration, enterprise-level system transitions, and organization-wide structural changes
• Building and launching automation solutions that supplant CRM and task management platforms through Python and LLM APIs
• Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and minimize delays
• Driving projects from initial assessment through full deployment, applying validated playbooks and executive decision-making
• Demonstrating technical capability through a practical challenge that evaluates your ability to architect and deliver AI-centric solutions

What You Won't Be Doing

• Overseeing large personnel groups or depending on multiple reporting layers to achieve outcomes
• Participating in prolonged coordination sessions or waiting for collective agreement to advance
• Assigning critical technical work to IT departments or third-party contractors---you will design and implement solutions directly
• Operating in maintenance mode---this role centers on continuous transformation and rapid execution

Head Of Operations Key Responsibilities

Architect and implement AI-driven operational frameworks that remove manual intervention, reduce structural complexity, and enable scalable execution across Trilogy's international software portfolio.

Basic Requirements

• 5 years of operational leadership in business operations
• Experience making presentations to C-suite executives
• Experience writing automation in Python and integrate with LLM APIs
• Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
• Remote work capability with at least 6 hours of overlap with the CST time zone

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-DE-Berlin-HeadofOperatio.001 Benefits: MinSalary: 100 MaxSalary: SalaryCurrency: USD Remote Model: N/A Country Code: de

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 is the foundation of our competitive edge. We acquire software businesses rapidly and scale them with even greater speed. Sustaining this requires executives who engineer lean, automated infrastructure rather than addressing complexity through additional personnel.

You will take full ownership of comprehensive transformations spanning our worldwide portfolio. This may involve redesigning offboarding workflows for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI-driven agents, or constructing automation frameworks that remove thousands of hours of manual labor. Execution will be rapid, leveraging Python, LLM APIs, tools such as Cursor, Windsurf, and MCP---alongside a library of validated playbooks enabling you to concentrate on measurable results.

Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We function with reduced hierarchies, accelerated delivery cycles, and elevated standards compared to conventional enterprise settings. This represents an opportunity to generate large-scale impact without navigating bureaucratic obstacles or overseeing inflated organizational structures.

Steady-state operations are not part of our model. Transformation is never outsourced. We do not hire individuals who require approval or extensive support structures to produce results. Our focus is on a select group of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as core strategy. If this describes your approach---you will excel in this environment.