We're hiring operators who design and rebuild systems built for scale.Operational excellence drives Trilogy's competitive edge. We acquire software businesses at speed and scale them faster still. That requires leaders who can architect lean, automated systems—not expand teams to absorb complexity.You'll lead complete transformations across our worldwide portfolio. This might involve redesigning the offboarding process for over 1,200 employees after an acquisition, replacing Jira and Salesforce with AI agents, or developing automations that eliminate thousands of hours of manual work. You'll move quickly with Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—backed by battle-tested playbooks that keep you focused on delivery.Trilogy operates a portfolio of more than 100 products with disciplined efficiency. We work with fewer management layers, shorter decision cycles, and steeper expectations than conventional enterprise settings. You'll have the opportunity to create large-scale impact without navigating bureaucracy or overseeing sprawling teams.Steady-state operations aren't our model. We don't delegate transformation to outside firms. And we don't bring on people who require constant approval or extensive teams to produce results. We're seeking a select group of technically deep, execution-driven leaders who treat automation as leverage and velocity as core strategy. If that describes you—this environment will suit you well.
What You Will Be Doing
- Leading high-stakes operational projects including M&A integrations, enterprise platform migrations, and company-wide organizational shifts
- Building and launching automations that replace CRM and task systems using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and cut cycle time
- Driving initiatives end-to-end—from assessment through go-live—leveraging established playbooks and executive decision-making
- Working through a practical technical assessment to validate your capability in designing and building AI-first systems
What You Won’t Be Doing
- Building or managing large teams—you'll operate with minimal headcount dependency
- Attending prolonged coordination meetings or waiting for group consensus to proceed
- Handing off technical design or execution to IT departments or third-party vendors—you own architecture and implementation
- Running business-as-usual operations—your mandate is transformation and rapid execution
AI Operations Specialist Key Responsibilities
Architect and implement AI-first operational systems that remove manual effort, simplify complex workflows, and enable scalable execution across Trilogy's international software portfolio.
Basic Requirements
- Located in North America (California excluded), South/Central America, or Western Europe (time zones UTC -8 through UTC +2)
- 5+ years leading operations in enterprise software environments
- 3+ years in customer-facing functions (Support, Sales, Collections, or similar)
- Proven ability to develop automation using Python and integrate LLM APIs
- Hands-on experience with Cursor, Windsurf, MCP, or comparable tools to deliver production-ready automations
- Track record of executing quickly, thinking autonomously, and delivering mission-critical outcomes without close supervision
Nice-to-have Requirements
- Background in leading major organizational changes such as M&A integrations or large-scale workforce transitions
- Track record of building and deploying AI-powered operational systems
- Catalog of automations you've designed and delivered at enterprise scale
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-IN-COUNTRY-AIOperationsSp.003
