Sr. Manager, People Engagement

At ClickUp, we're building the future of work: the first truly converged AI workspace unifying tasks, docs, chat, calendar, and enterprise search, all supercharged by context-driven AI. We are an AI-native company. Every team member is expected to leverage AI daily, and we evaluate AI fluency as part of our hiring process. Join us and help redefine what's possible. 🚀 ClickUp is seeking a Senior Manager, People Engagement who has deep experience building and scaling seamless, compliant global people operations programs, from first-day onboarding through off-boarding, content governance, learning programs, company-wide program management, and AI-powered automation. This individual brings a strong command of Workday HCM, Deel, and global Right to Work (RTW) compliance, paired with a forward-thinking approach to leveraging AI agents and emerging technologies to drive operational excellence across the full employee lifecycle. The ideal candidate understands that operational rigor and human-centered design go hand in hand. You have a proven track record of leading cross-functional teams to deliver programs that are both compliant and deeply thoughtful. You think in systems, lead with data, and are energized by the opportunity to use technology, including AI agents and automations, to scale operations, reduce manual work, and elevate the employee experience. If you're a strategic operator who thrives at the intersection of people, process, and innovation... this role is for you! THE ROLE: As the Senior Manager, People Engagement, reporting to the VP of People Technology & Programs, you will own and drive critical people operations functions spanning the full employee lifecycle. From architecting world-class onboarding and off-boarding experiences, to managing learning platforms and company programs, to building and governing AI agents that power operational scale, you will lead a dedicated team to ensure ClickUp's people operations are seamless, compliant, and continuously improving. GLOBAL ONBOARDING & OFFBOARDING - Own the end-to-end global onboarding process: Right to Work, background checks, IT coordination, Deel operations for international hires/contractors, and cross-team logistics to ensure every new joiner is set up from day one. - Manage pre-hire and former employee queries as the primary point of contact. - Design and maintain a "White Glove" onboarding experience for Executive Leadership. - Own separation document generation (state-specific docs, separation letters, COEs) with accuracy and legal compliance. - Define and track lifecycle KPIs: onboarding satisfaction, RTW completion, training, benefits enrollment, equity acknowledgment. - Partner with People Systems to optimize employee support operations (intake, routing, metrics, self-service). CONTENT GOVERNANCE - Own the employee knowledge ecosystem: ensure policies and resources are discoverable, accurate, and governed through clear ownership, review cadences, and escalation paths. WORKDAY LEARNING & EDUCATIONAL PROGRAMS - Manage security training rollouts and configure new modules (SCORM, video) in Workday Learning. - Audit learning data, enforce completion requirements, and manage non-compliance escalations. - Oversee professional development programs and vendor manage learning content partners (OpenSesame, etc.). COMPANY PROGRAM MANAGEMENT - Operationally own AwardCo (config, vendor, budget, comms), co-working space access, and Performance Awards logistics. AI AGENT INFRASTRUCTURE & MANAGEMENT - Own and govern AskPeople Pal (ticket triage/routing) and any future AI agents; lead health checks, documentation, and continuous improvement standards. - Build and maintain ClickUp automations supporting operational workflows. - Serve as the People Team's go-to resource for AI adoption, training, and support. QUALIFICATIONS: - 5+ years of experience in HR/People Operations, with at least 3+ years in a senior lead or people manager capacity overseeing global programs. - High