This role is designed for operators who design and scale systems from the ground up.Operational excellence is not optional at Trilogy—it is a strategic differentiator. We acquire software companies rapidly and scale them at pace. To sustain this velocity, we require leaders who engineer lean, automated systems rather than solve problems by adding headcount.You will take ownership of transformations spanning our global portfolio. This may involve redesigning offboarding workflows for 1,200+ employees following an acquisition, replacing platforms like Jira and Salesforce with AI agents, or creating automations that remove thousands of manual hours. Your execution will be swift, powered by Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep you focused on outcomes.Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We operate with reduced hierarchy, accelerated cycles, and elevated standards compared to traditional enterprise settings. This is an opportunity to generate meaningful impact at scale without navigating bureaucracy or managing oversized teams.We do not maintain status quo operations. We do not outsource transformation work. And we do not hire individuals who require consensus or large teams to execute. We seek a limited number of technically proficient, execution-oriented leaders who leverage automation and prioritize speed. If this describes you, you will excel here.
What You Will Be Doing
- Driving high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
- Building and deploying automations that replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-enabled workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce cycle time
- Owning initiatives end-to-end—from diagnosis through deployment—guided by proven playbooks and executive-level decision-making
- Completing a practical technical assessment to validate your capability to architect and deliver AI-first solutions
What You Won’t Be Doing
- Building or managing large teams—you will rely on technology, not layers of people
- Participating in prolonged alignment meetings or waiting for consensus to proceed
- Handing off technical work to IT or external vendors—you will design and implement the solution directly
- Operating in steady-state mode—this role centers on transformation and speed
AI Operations Specialist Key Responsibilities
Architect and deliver AI-first operational systems that remove manual overhead, simplify complexity, and enable scalable execution across Trilogy's worldwide software portfolio.
Basic Requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years of operational leadership within enterprise software
- 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
- Proven ability to develop automation using Python and integrate with LLM APIs
- Hands-on experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable tools
- Track record of executing quickly, thinking autonomously, and delivering high-stakes outcomes without supervision
Nice-to-have Requirements
- Background leading major organizational transitions such as M&A integrations or large-scale offboarding
- Track record designing and launching AI-driven operational systems
- Portfolio showcasing automations you have personally built 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.004
