Head of Operations, Trilogy (Remote) - $200,000/year ...

OverviewHead of Operations, Trilogy (Remote) - $200,000/year USDBase pay range: $100.00/hr - $100.00/hrELITE OPERATORS WANTED: Build the Systems That Outperform the Industry. At Trilogy, operational excellence isn't a nice-to-have; it's our unfair advantage. We acquire software companies fast, and we scale them even faster. To keep up, we need executives who can design and deliver lean, automated systems—not manage complexity with headcount.What You Will Be DoingExecute high-stakes operational transformations including M&A integrations, enterprise system migrations, and organizational restructures with measurable business impactDesign and deploy AI-powered automations that replace traditional CRM and task management systems using Python and advanced LLM APIsBuild scalable workflows via Cursor, Windsurf, and MCP that systematically eliminate manual effort across the organizationLead mission-critical initiatives from strategic diagnosis to technical implementation using executive judgment and Trilogy's battle-tested playbooksDemonstrate your technical capabilities through a hands-on challenge focused on designing and implementing AI-first operational solutionsWhat You Won’t Be DoingOverseeing large teams or building organizational hierarchies to accomplish objectivesWasting time in consensus-building meetings or navigating bureaucratic approval chainsOutsourcing the technical implementation to IT departments or third-party vendors—you'll architect and execute solutions directlyMaintaining status quo operations—this role exists exclusively to drive transformation and velocityHead Of Operations Key ResponsibilitiesDesign and deploy AI-first operational systems that eliminate manual effort, compress complexity, and drive scalable execution across Trilogy's global software portfolio.Basic RequirementsBased in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)5+ years of operational leadership in enterprise software with demonstrated results3+ years in customer-facing roles (Support, Sales, Collections, etc.)Proven ability to write production-grade automation in Python and integrate with LLM APIsHands-on experience using Cursor, Windsurf, MCP, or similar tools to build and deploy automationsDemonstrated capacity to execute independently, make high-stakes decisions, and deliver results without supervisionNice-to-have RequirementsTrack record leading complex organizational transitions such as M&A integrations or large-scale workforce restructuringDocumented success designing and implementing AI-driven operational systems that deliver measurable business outcomesPortfolio of self-built automations deployed at enterprise scale with quantifiable impact metricsAbout TrilogyHundreds of software businesses run on the Trilogy Business Platform. Trilogy is known for seeking top talent, innovating new technology, and incubating new businesses. Our approach centers on customer-facing design and scalable cloud-based stack growth. Trilogy is a place to grow your career with great people and meaningful work.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. For details, see Job Code: LJ-5145-US-Seattle-HeadofOperatioSeniority levelDirectorEmployment typeFull-timeJob functionManagementEngineeringStrategy/PlanningIndustriesSoftware DevelopmentIT Services and IT ConsultingTechnology, Information and Internet #J-18808-Ljbffr

Created: 2025-09-17