This position is designed for operators capable of constructing and reconstructing systems that achieve scale.Operational excellence at Trilogy is not optional—it serves as our competitive edge. We acquire software companies quickly and scale them with even greater speed. Sustaining this pace demands executives who can architect and implement lean, automated systems rather than address complexity by expanding teams.You will take ownership of complete transformations spanning our global portfolio. This might involve redesigning the offboarding process for over 1,200 employees following acquisition, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of manual work hours. Execution will be rapid, leveraging Python, LLM APIs, tools such as Cursor, Windsurf, and MCP—supported by a collection of validated playbooks that allow you to concentrate on results.Trilogy manages a portfolio exceeding 100 products with uncompromising efficiency. We function with reduced hierarchy, accelerated cycles, and elevated standards compared to conventional enterprise settings. This opportunity enables you to generate large-scale impact without navigating bureaucracy or overseeing inflated teams.Steady-state operations are not part of our model. Transformation is never outsourced. We do not recruit individuals who require authorization or substantial teams to produce results. Our search is for a select group of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as a strategic asset. If this describes you—this environment will suit you well.
What You Will Be Doing
- Driving high-complexity operational initiatives including M&A integrations, enterprise system transitions, and large-scale organizational changes
- Architecting and delivering automations that supplant CRM and task management platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and minimize latency
- Owning projects from initial assessment through full deployment, applying established playbooks and executive decision-making
- Undertaking a practical technical assessment to validate your capacity to architect and deploy AI-first solutions
What You Won’t Be Doing
- Overseeing large teams or depending on organizational layers to accomplish objectives
- Attending protracted alignment sessions or waiting for consensus before taking action
- Assigning the technical heavy lifting to IT departments or third-party vendors—you will design and execute solutions directly
- Running steady-state operations—this position centers on transformation and speed
AI Operations Specialist Key Responsibilities
Architect and implement AI-first operational systems that remove manual labor, reduce complexity, and enable scalable execution throughout Trilogy's global software portfolio.
Basic Requirements
- Located in North America (California excluded), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years of operational leadership within enterprise software environments
- 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
- Confirmed capability to develop automation using Python and integrate with LLM APIs
- Experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable tools
- Established track record of moving quickly, thinking autonomously, and producing high-stakes outcomes without supervision
Nice-to-have Requirements
- Background leading large-scale organizational transitions including M&A integrations or mass offboarding initiatives
- Track record architecting and implementing AI-powered operational systems
- Collection of automations you have personally developed and deployed at 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.001
