User Operations Generalist - Enterprise Billing & Product (Contract)

Perplexity AI is a startup focused on enhancing user experience through their AI-powered search and answer engine. They are seeking a User Operations Generalist who will manage user inquiries, particularly in billing and product support for Enterprise customers, while collaborating with various teams to improve processes and user satisfaction.

Responsibilities:

• Provide fast, accurate, and empathetic support across all active channels (email, chat, Slack, community)
• Handle a broad range of user inquiries: account issues, product questions, feature guidance, bug reports, and general troubleshooting for both consumer and enterprise users
• Triage and prioritize incoming volume effectively, ensuring response and resolution times stay on target
• Develop deep product knowledge to assist users confidently across all areas of the platform, including Enterprise Pro features and configurations
• Serve as a primary support contact for Perplexity Enterprise customers, working with them via tickets, Slack, and calls to resolve complex technical and product questions
• Build durable relationships with enterprise users and stakeholders, advising on best practices and helping them maximize value from the platform
• Own end-to-end troubleshooting for enterprise issues: reproduce problems, isolate root causes, collaborate with engineers, and communicate clear, low-jargon explanations
• Capture structured feedback from enterprise customers and champion their needs in roadmap discussions with Product
• Support enterprise onboarding, configuration questions, and adoption—guiding teams through SSO setup, workspace management, and platform best practices
• Escalate complex enterprise issues appropriately while maintaining ownership of resolution and follow-through
• Own billing-related inquiries for both consumer and enterprise customers: subscription management, payment failures, refunds, cancellations, plan changes, and account modifications
• Investigate and resolve billing discrepancies using Stripe and internal tools, including enterprise invoicing and multi-seat licensing scenarios
• Manage chargeback cases—investigation, documentation, and representment
• Handle multi-currency and international billing scenarios as needed
• Align with your Consumer billing counterpart on escalation paths, refund policies, and documentation standards to deliver a consistent experience across consumer and enterprise—and surface cross-cutting trends so insights from one side drive improvements on the other
• Troubleshoot product and feature issues, reproduce bugs, and guide users through workarounds
• Spot patterns across tickets—recurring bugs, confusing UX, billing errors, enterprise-specific pain points—and flag them to Product and Engineering with clear, actionable context
• File bugs and tasks in Linear with enough detail for engineering to act on them
• Contribute feedback from support interactions to inform product roadmap prioritization
• Write and maintain Help Center articles, FAQs, and guides covering billing, product features, account management, enterprise onboarding, and common troubleshooting
• Design and maintain use-case flows, playbooks, and internal runbooks that help teammates and customers solve recurring challenges faster
• Build internal documentation—SOPs, decision trees, macros, escalation playbooks—to keep the team consistent as we scale
• Proactively update documentation as new features, billing models, and enterprise configurations launch
• Identify workflow inefficiencies and propose improvements—better macros, smarter routing, automation opportunities, self-service solutions
• Share knowledge with teammates and contribute to raising the team's capabilities across billing, product, and enterprise support
• Collaborate cross-functionally with Engineering, Product, Finance, and Enterprise GTM to resolve complex issues and improve the user experience
• Track and report on support KPIs (response time, CSAT, resolution rates) and propose data-driven process improvements
• Help build and refine support processes as the team and product grow

Requirements:

• 3+ years in customer support, user operations, or a similar generalist support role—ideally in tech or SaaS
• Meaningful experience handling billing and payment support (subscription management, refunds, disputes)
• Experience supporting enterprise or B2B customers, including working directly with business stakeholders on complex, multi-touch issues
• Working knowledge of Stripe or a comparable payment platform
• Experience supporting users across multiple channels simultaneously in a fast-paced, high-volume environment
• Strong written communication—clear, concise, and adaptable to the audience (end users, enterprise stakeholders, engineers, leadership)
• Self-motivated and independent: you manage your own priorities, take initiative, and deliver without waiting for direction—but you proactively ask questions for clarity and process alignment
• Effective internal communicator: you keep the team informed, surface context and blockers early, and make sure nothing slips
• Experience creating user-facing and internal documentation (Help Center content, SOPs, templates, guides)
• Comfortable spotting trends and patterns in ticket data and translating them into actionable feedback or process improvements
• Adaptable to a startup environment: comfortable with ambiguity, shifting priorities, and rapid change
• Experience with Intercom, Linear, Notion, and Google Sheets
• Familiarity with AI/ML products, LLMs, or search technologies
• Ability to translate complex technical concepts—APIs, SSO/SAML, cloud integrations—into clear, actionable guidance for non-technical stakeholders
• Knowledge of enterprise identity (SSO/OAuth) and cloud-storage ecosystems (Google Drive, SharePoint, Dropbox)
• Experience at an early-stage or high-growth startup
• Background in chargeback management or dispute resolution
• Proficiency with data analysis tools (SQL, Looker, Snowflake) is a plus
• Interest in support automation, workflow optimization, or tooling improvements