User Operations Generalist - Enterprise Billing & Product (Contract)

Perplexity•San Francisco, CA

About The Position

We're looking for a User Operations Generalist with strong billing and product support skills to join our CX team. This is a generalist role first—you'll handle the full range of user inquiries across channels, from account questions and product troubleshooting to bug reports and feature guidance. Where you'll go deeper is billing and product support, with a heavy emphasis on Enterprise: managing subscription and billing issues for both consumer and enterprise customers, troubleshooting complex Enterprise Pro configurations, and serving as a trusted point of contact for enterprise users navigating the platform. You'll work directly with Enterprise customers via tickets, Slack, and emails, diagnosing their most complex issues and acting as the last line of defense before Product and Engineering step in. You'll build relationships with enterprise stakeholders, capture structured feedback, and champion their needs in product discussions. You're a strong, independent operator who doesn't need to be told what to do next. Here's what that looks like in this role: You see the gap—whether it's a missing Help Center article, a broken billing workflow, or a pattern in enterprise tickets—and you move to fix it You're self-motivated and take initiative, but you also know when to ask questions and communicate effectively with the team You keep people informed, surface blockers early, and make sure nothing falls through the cracks You thrive when given ownership and trust—we won't hold your hand, and you wouldn't want us to Our CX operations are still maturing—while we have some foundational processes in place, there's a lot left to build. You'll need an entrepreneurial mindset and be comfortable with ambiguity as you help shape how we support our users at scale.

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

Nice To Haves

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

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