OverviewThis position is designed for operators capable of designing and redesigning systems built to scale. Operational excellence at Trilogy is a core differentiator. We acquire software businesses rapidly and scale them with speed. Sustaining this pace requires executives who design lean, automated infrastructure—not those who solve problems by expanding headcount.You will take ownership of comprehensive transformations spanning our global portfolio. Examples include redesigning offboarding processes for 1,200+ employees following acquisition, substituting traditional tools like Jira and Salesforce with AI agents, or deploying automations that remove thousands of hours of manual effort. Execution will be rapid, leveraging Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of validated playbooks that prioritize delivery.Trilogy manages a portfolio exceeding 100 products with disciplined efficiency. We function with reduced hierarchy, accelerated execution cycles, and elevated performance standards compared to conventional enterprise settings. This chance offers impact at scale without navigating bureaucracy or overseeing inflated teams.What You Will Be DoingDelivering high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitionsBuilding and deploying automations to replace CRM and task management platforms using Python and LLM APIsImplementing AI-powered workflows through Cursor, Windsurf, and MCP to remove manual tasks and reduce cycle timeOwning initiatives from initial assessment through full deployment,



applying proven playbooks and executive-level decision-makingPassing a hands-on technical assessment that validates your capability to design and implement AI-first solutionsWhat You Won’t Be DoingOverseeing large teams or depending on organizational layers to accomplish objectivesAttending prolonged alignment sessions or waiting for consensus before actingHanding off the technical work to IT departments or third-party vendors—you will design and execute the solution directlyRunning steady-state operations—this role centers on transformation and speedHead Of Operations Key ResponsibilitiesArchitect and implement AI-first operational systems that remove manual work, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.Basic Requirements5+ years of operational leadership in business operationsExperience presenting to C-suite executivesExperience building automation in Python and integrating with LLM APIsExperience deploying production-grade automations using Cursor, Windsurf, MCP, or comparable toolsAbility to work remotely with a minimum of 6 hours overlap with the CST time zoneAbout TrilogyHundreds 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 usThis 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-Vancouve-HeadofOperatio.001#J-18808-Ljbffr

📌 Head Of Operations, Trilogy (Remote) - $200,000/Year Usd - $200,000 A Year - Remote (Toronto)
🏢 Trilogy
📍 Toronto