Director of Operational Excellence, Trilogy (Remote) - $200,000/year USD

Join us at Trilogy, where operational excellence is not just a goal, but our strategic edge. If you're an innovator who thrives on designing scalable systems, this role is your next challenge.

What You Will Be Doing

• Driving transformative projects such as M&A integrations and enterprise system migrations with high complexity.
• Crafting and deploying automations to replace traditional CRM and task management tools utilizing Python and LLM APIs.
• Implementing AI-powered workflows using tools like Cursor, Windsurf, and MCP to streamline operations.
• Leading projects from initial diagnosis through to deployment with a focus on strategic execution.
• Participating in hands-on technical challenges to showcase your ability to create AI-first solutions.
  
  

What You Won’t Be Doing

• Managing large teams or depending on multiple layers of staff to accomplish goals.
• Enduring endless meetings for alignment or waiting for consensus to take action.
• Handing off difficult tasks to IT or external vendors—you're the architect and executor here.
• Maintaining routine operations—this role is about transformation and speed.
  
  

Director Of Operational Excellence Key Responsibilities

Implement AI-driven operational frameworks that reduce manual workload, streamline complexity, and enhance scalable execution across Trilogy's global software portfolio.

Basic Requirements

• Based in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
• 5+ years of operational leadership in enterprise software
• 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
• Proven expertise in writing automation scripts in Python and integrating with LLM APIs
• Experience with Cursor, Windsurf, MCP, or similar tools for developing production-grade automations
• Ability to operate independently, make swift decisions, and deliver critical results without supervision
  
  

Nice-to-have Requirements

• Experience in leading large organizational changes such as M&A integrations or large-scale offboarding
• A track record of designing and implementing AI-driven operational systems
• A collection of automations you've 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-CA-Calgary-DirectorofOper