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

Job Description:

This position is designed for operators capable of designing and redesigning systems built to scale.

​

Operational excellence at Trilogy is not optional—it is a core competitive differentiator. We acquire software businesses rapidly and scale them with even greater speed. Sustaining this pace requires executives who design lean, automated infrastructure—not those who solve problems by expanding headcount.

​

You will take ownership of comprehensive transformations spanning our global portfolio. Examples include redesigning offboarding processes for 1,200+ employees following acquisition, substituting traditional tools like Jira and Salesforce with AI agents, or deploying automations that remove thousands of hours of manual effort. Execution will be rapid, leveraging Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of validated playbooks that prioritize delivery.

​

Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We function with reduced hierarchy, accelerated execution cycles, and elevated performance standards compared to conventional enterprise settings. This opportunity offers impact at scale without navigating bureaucracy or overseeing inflated teams.

​

Steady-state operations are not our focus. Transformation is not outsourced. We do not recruit individuals who require approval or extensive teams to produce results. Our search is for a select group of technically proficient, execution-oriented leaders who apply automation as leverage and velocity as methodology. If this describes you—this environment will suit you well.

​

What You Will Be Doing

​

• Delivering high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
• Building and deploying automations to replace CRM and task management platforms using Python and LLM APIs
• Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual tasks and reduce cycle time
• Owning initiatives from initial assessment through full deployment, applying proven playbooks and executive-level decision-making
• Passing a hands-on technical assessment that validates your capability to design and implement AI-first solutions

​

What You Won’t Be Doing

​

• Overseeing large teams or depending on organizational layers to accomplish objectives
• Attending prolonged alignment sessions or waiting for consensus before acting
• Handing off the technical work to IT departments or third-party vendors—you will design and execute the solution directly
• Running steady-state operations—this role centers on transformation and speed

​

Head Of Operations Key Responsibilities

​

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

​

Basic Requirements

​

• 5+ years of operational leadership in business operations
• Experience presenting to C-suite executives
• Experience building automation in Python and integrating with LLM APIs
• Experience deploying production-grade automations using Cursor, Windsurf, MCP, or comparable tools
• Ability to work remotely with a minimum of 6 hours 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-US-COUNTRY-HeadofOperatio.010