This position is designed for operators capable of constructing and reconstructing scalable systems.
Operational excellence at Trilogy is not optional—it is the competitive edge that defines us. We move quickly to acquire software companies and accelerate their growth even faster. Success in this environment demands executives who can architect lean, automated systems rather than address complexity through expanded headcount.
You will take ownership of comprehensive transformations spanning our global portfolio. This may involve redesigning the offboarding process for over 1,200 employees following acquisitions, substituting Jira and Salesforce with AI agents, or deploying automations that remove thousands of manual hours from workflows. Execution speed is essential, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by battle-tested playbooks that allow you to concentrate on measurable outcomes.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We function with reduced hierarchy, accelerated cycles, and elevated performance standards compared to conventional enterprise settings. This is an opportunity to create large-scale impact without navigating bureaucracy or overseeing oversized teams.
Steady-state operations are not part of our model. Transformation is not outsourced. We do not recruit individuals who require approval or extensive teams to execute. We seek a select group of deeply technical, execution-driven leaders who treat automation as leverage and speed as a core strategic principle. If this describes you, you will excel here.
What You Will Be Doing
- Delivering high-complexity operational projects including M&A integrations, enterprise system migrations, and organization-wide transitions at scale
- Building and launching automations that displace CRM and task management platforms using Python and LLM APIs
- Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual tasks and minimize latency
- Driving initiatives from initial diagnosis through full deployment, applying established playbooks and executive-level decision-making
What You Won’t Be Doing
- Overseeing large teams or depending on multiple layers of personnel to accomplish objectives
- Attending prolonged alignment sessions or waiting for consensus before taking action
- Handing off the complex work to IT departments or third-party vendors—you will design and implement the solution directly
- Operating in steady-state mode—this role centers on transformation and rapid execution
Director Of Operational Excellence Key Responsibilities
Architect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution throughout 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-ES-COUNTRY-DirectorofOper.013
Crossover