Operations AI Lead, Trilogy (Remote) - $200,000/year USD
Crossover · United States
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- Hybrid
- Full-time
- $200,000 / year
- United States
Job highlights
- Lead AI-driven operational transformations globally.
- Automate complex business processes with Python, LLMs.
- Replace enterprise tools using AI agents.
- Drive end-to-end project execution rapidly.
- Requires strong Python and AI integration skills.
About the role
Operations AI Lead at Trilogy
This role is built for operators who engineer and re-engineer systems designed to scale. Operational excellence at Trilogy is not optional—it's our competitive edge. We acquire software companies at speed and scale them even faster. To sustain this, we require leaders capable of architecting lean, automated systems—not expanding complexity through additional headcount.
What You Will Be Doing
- Executing operationally complex projects including M&A integrations, enterprise system migrations, and large-scale organizational transitions.
- Architecting and delivering automations that replace CRM and task management platforms using Python and LLM APIs.
- Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual processes and reduce execution latency.
- Driving initiatives end-to-end from diagnosis through deployment, applying proven playbooks and executive decision-making.
- Completing a practical technical challenge that validates your capability to design and deliver AI-first solutions.
What You Won’t Be Doing
- Overseeing large teams or depending on multiple layers of people to achieve results.
- Attending prolonged alignment meetings or waiting for consensus before taking action.
- Handing off the difficult work to IT departments or external vendors—you will design and execute the solution directly.
- Running steady-state operations—this role is centered on transformation and execution speed.
Operations AI Lead Key Responsibilities
Architect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution across Trilogy's global 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-US-COUNTRY-OperationsAILe.003
Key skills/competency
- Operations AI Lead
- System Re-engineering
- Lean Automation
- Python
- LLM APIs
- M&A Integrations
- Enterprise System Migration
- AI-Powered Workflows
- Independent Contractor
- C-suite Presentations
Skills & topics
- Operations AI Lead
- AI
- Automation
- Python
- LLM
- System Re-engineering
- M&A Integration
- Enterprise Systems
- Operational Excellence
- Remote
How to get hired
- Tailor your resume: Highlight your 5+ years in operational leadership and Python automation experience. Quantify achievements in M&A integrations and system migrations.
- Showcase C-suite impact: Detail experience presenting to executives, demonstrating your communication and strategic influence.
- Demonstrate technical proficiency: Emphasize your hands-on experience with Python, LLM APIs, and tools like Cursor, Windsurf, or MCP.
- Embrace the contractor model: Understand the independent contractor agreement and remote work requirements, including CST overlap.
- Prepare for the challenge: Be ready to showcase your AI-first solution design and delivery capabilities through a practical technical assessment.
Technical preparation
Behavioral questions
Frequently asked questions
- What is the primary focus of the Operations AI Lead role at Trilogy?
- The Operations AI Lead role at Trilogy focuses on architecting and executing AI-first operational transformations across the company's global portfolio. This involves re-engineering systems, automating manual processes, and replacing enterprise tools with AI-driven agents to drive efficiency and scale.
- What technical skills are essential for the Operations AI Lead position at Trilogy?
- Essential technical skills include 5+ years of operational leadership, strong Python programming for automation, experience integrating with LLM APIs, and familiarity with tools like Cursor, Windsurf, or MCP for shipping production-grade automations.
- Does Trilogy offer traditional employment for the Operations AI Lead role?
- No, this is a full-time, long-term position structured as an independent contractor agreement with Crossover. Compensation is paid hourly, totaling $200,000 USD annually based on a 40-hour work week.
- How does Trilogy's operational approach differ from traditional companies?
- Trilogy operates with fewer organizational layers, shorter cycles, and elevated standards, prioritizing speed and efficiency. They focus on transformation and rapid execution rather than steady-state operations or reliance on large teams.
- What kind of projects can I expect to work on as an Operations AI Lead at Trilogy?
- You can expect to work on complex projects such as M&A integrations, enterprise system migrations, large-scale organizational transitions, and implementing AI-powered workflows to replace tools like Jira and Salesforce.
- What is the work arrangement for the Operations AI Lead role?
- This is a remote position. Candidates must have the capability to work remotely and maintain at least 6 hours of overlap with the Central Standard Time (CST) time zone.
- How is compensation handled for the Operations AI Lead role?
- Compensation is $100 USD per hour, totaling $200,000 USD per year for a 40-hour work week (50 weeks per year). Payments are processed weekly through an independent contractor agreement with Crossover.
- Will I be managing a large team in this Operations AI Lead role?
- No, this role is designed for individual execution and leadership without overseeing large teams. The focus is on architecting and implementing solutions directly, rather than managing people to achieve results.