User Operations Generalist - Enterprise Billing & Product (Contract)

About the Team

The User Operations team at Perplexity AI is the frontline of our user experience. We ensure that our AI-powered search and answer engine delivers real value to millions of consumer users and a growing base of Enterprise Pro customers. Our team operates across 3-4 active support channels—email, in-app messaging, Slack, and community—and collaborates closely with Product, Engineering, Finance, and Enterprise GTM to turn user feedback into product improvements. We're a lean, fast-moving group at a startup that ships constantly, so everyone on the team wears multiple hats and contributes well beyond just resolving tickets.

About the Role

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.

Key Responsibilities

Multi-Channel User Support

• 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

Enterprise Customer Support

• 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

Billing & Subscription Support

• 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

Product Support & Issue Identification

• 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

Documentation & Help Center

• 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

Process Improvement & Collaboration

• 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

Qualifications

Required

• 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

Preferred

• 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

Who You Are

• A generalist at heart who can flex across product, billing, enterprise, and technical support without missing a beat

• Strong and self-motivated—you take ownership, drive things forward, and don't wait to be told what to do

• Proactive—you see something that needs doing and you do it, whether it's a missing Help Center article, a broken workflow, or an enterprise customer who needs follow-up

• A clear, effective communicator internally—you keep the team in the loop, share context generously, flag issues early, and ask smart questions when something is unclear

• Independent but not siloed—you don't need hand-holding, but you understand that asking questions and aligning on process makes the whole team stronger

• Comfortable building relationships with enterprise customers and acting as their advocate internally

• Curious and product-minded—you care about the user experience beyond the individual ticket

• Detail-oriented and efficient—you balance quality with speed in everything you do

• High ownership and a "do-what-it-takes" mindset in ambiguous situations