Operations AI Innovator, Trilogy (Remote) - $200,000/year USD

This position is designed for operators capable of building and restructuring systems at scale.At Trilogy, operational excellence represents our competitive edge—not an optional feature. We acquire software companies rapidly and scale them with even greater speed. To sustain this pace, we require executives who can architect and implement lean, automated systems rather than address complexity through increased headcount.You'll take ownership of complete transformations spanning our global portfolio. This might involve redesigning the offboarding process for 1,200+ employees following acquisitions, substituting Jira and Salesforce with AI agents, or creating automations that remove thousands of manual hours from workflows. Execution will be swift, leveraging Python, LLM APIs, tools such as Cursor, Windsurf, and MCP—supported by a collection of battle-tested playbooks that enable outcome-focused work.Trilogy manages a portfolio of 100+ products with disciplined efficiency. We function with reduced organizational layers, accelerated cycles, and elevated standards compared to conventional enterprise settings. This opportunity allows you to generate impact at scale without navigating bureaucracy or overseeing inflated teams.Steady-state operations are not part of our model. We don't outsource transformation initiatives. And we don't bring on people who require authorization or large teams to produce results. We're seeking a limited number of deeply technical, execution-oriented leaders who leverage automation and treat speed as a strategic advantage. If this describes you—you'll excel here.What You Will Be DoingLeading high-complexity operational initiatives including M&A integrations, enterprise system migrations, and large-scale organizational transitionsArchitecting and delivering automations that replace CRM and task management platforms using Python and LLM APIsImplementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and decrease latencyDriving projects from assessment through deployment, applying proven playbooks and executive-caliber decision-makingUndertaking a practical technical challenge to validate your capability to design and build AI-first solutionsWhat You Won't Be DoingOverseeing large teams or depending on multiple organizational layers to accomplish objectivesAttending prolonged alignment sessions or waiting for consensus to advanceHanding off the difficult work to IT departments or external vendors—you'll design and build the solution directlyOperating steady-state functions—this position centers on transformation and speedOperations AI Innovator Key ResponsibilitiesArchitect and implement AI-first operational systems that remove manual effort, reduce complexity, and enable scalable execution across Trilogy's global software portfolio.Basic Requirements5+ years of operational leadership in business operationsExperience making presentations to C-suite executivesExperience writing automation in Python and integrate with LLM APIsExperience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automationsRemote work capability with at least 6 hours of 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.#J-18808-Ljbffr