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

This position is built for operators who design and redeploy scalable systems from the ground up.

Operational excellence at Trilogy is not optional—it's the competitive edge. We move quickly to acquire software businesses and scale them even more rapidly. Sustaining that pace requires executives capable of architecting lean, automated infrastructures—not solving problems by adding headcount.

You'll take ownership of complete transformations spanning our worldwide portfolio. Examples include reengineering offboarding workflows for 1,200+ employees after an acquisition, displacing legacy tools like Jira and Salesforce with AI-driven agents, or deploying automations that erase thousands of manual work hours. Execution will be rapid, powered by Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by battle-tested playbooks that keep your focus on measurable results.

Trilogy manages a portfolio of 100+ products with uncompromising efficiency. We function with minimal hierarchy, compressed decision cycles, and standards that exceed those of conventional enterprise settings. This opportunity lets you create large-scale impact without navigating bureaucracy or overseeing inflated teams.

We do not maintain static operations. We do not delegate transformation to third parties. And we do not hire individuals who require extensive approval chains or sizable teams to deliver outcomes. We seek a select group of deeply technical, execution-oriented leaders who treat automation as leverage and velocity as strategy. If that describes you—this environment will suit you well.

What You Will Be Doing

* Driving high-stakes operational initiatives including M&A integrations, enterprise-wide system migrations, and organization-level transitions

* Building and shipping automations that displace traditional CRM and task management platforms through Python and LLM APIs

* Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and cut cycle time

* Owning projects end-to-end—from analysis through launch—applying established playbooks and executive-caliber decision-making

* Passing a practical technical assessment that validates your capability to architect and deliver AI-native solutions

What You Won’t Be Doing

* Building or managing large teams, or depending on organizational layers to accomplish objectives

* Attending prolonged coordination sessions or waiting for group consensus before acting

* Handing off complex work to IT departments or outside contractors—you will design and implement solutions directly

* Overseeing business-as-usual operations—this position centers on transformation and speed

Director Of Operational Excellence Key Responsibilities

Architect and implement AI-native operational frameworks that remove manual overhead, simplify complexity, and enable scalable execution across Trilogy's international 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-NL-Amsterda-DirectorofOper.013