Job Specifications
This is a role for operators capable of designing and rebuilding systems at scale.
Operational excellence at Trilogy isn't optional—it's the foundation of our competitive edge. We acquire software companies rapidly and scale them even faster. To sustain this pace, we require executives who can architect lean, automated systems rather than add layers of complexity through hiring.
You will take ownership of end-to-end transformations across our global portfolio. This might involve restructuring how we offboard 1,200+ employees following acquisitions, displacing Jira and Salesforce with AI agents, or creating automations that remove thousands of hours of manual labor. Execution will be fast, leveraging Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—alongside a library of battle-tested playbooks that enable you to prioritize results.
Trilogy manages a portfolio of 100+ products with disciplined efficiency. We function with reduced hierarchy, accelerated timelines, and elevated standards compared to conventional enterprise settings. This is an opportunity to generate impact at scale without navigating bureaucracy or overseeing bloated organizational structures.
Steady-state operations aren't part of our model. We don't delegate transformation to third parties. And we don't bring on people who require extensive approval or large teams to execute. We seek a select group of highly technical, execution-driven leaders who treat automation as leverage and velocity as core strategy. If that describes you—this environment will suit you well.
What You Will Be Doing
Leading high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitions
Building and deploying automations to replace CRM and task management platforms using Python and LLM APIs
Implementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual effort and decrease cycle time
Driving projects from initial assessment through full deployment, applying established playbooks and executive-level decision-making
Passing a hands-on technical assessment that validates your capacity to architect and deliver AI-first solutions
What You Won’t Be Doing
Overseeing large teams or depending on hierarchical structures to achieve outcomes
Attending prolonged alignment sessions or waiting for consensus before advancing
Handing off the complex work to IT departments or outside consultants—you will design and implement the solution directly
Running steady-state operations—this position centers on transformation and speed
Director Of Operational Excellence Key Responsibilities
Architect and implement AI-first operational systems that remove manual processes, reduce complexity, and enable scalable execution throughout Trilogy's global 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 in enterprise software
3+ years in customer-facing roles (Support, Sales, Collections, etc.)
Proven capability to develop automation using Python and integrate with LLM APIs
Experience deploying production-grade automations with Cursor, Windsurf, MCP, or comparable tools
Track record of moving quickly, thinking autonomously, and delivering high-stakes outcomes without micromanagement
Nice-to-have Requirements
Background leading large-scale organizational changes such as M&A integrations or mass offboarding
Track record of architecting and launching AI-driven operational systems
Collection of automations you have 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-Toronto-DirectorofOper.002
About the Company
Crossover is a global recruitment company, founded in 2014. We're the world's largest recruiter that specializes in elite full-time remote jobs, hiring the top 1% of tech talent from every corner of the planet.
We find awesome talent in overlooked places, by posting jobs all over the world, and giving everyone an equal opportunity to prove their skills are world-class. Our system of AI-powered assessments is based on objective factors that are scientifically proven to predict high performance (e.g. cognitive aptitude).
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