Billing Specialist

About Collective:

Collective is on a mission to redefine the way businesses-of-one work. Our technology and team of trusted advisors help members achieve financial independence by taking care of everything from business incorporation to accounting, bookkeeping, tax services, and access to a thriving community, all in one integrated platform. We believe in empowering self-employed people to enjoy the same tax savings that big companies get, so they can focus on their passion, not paperwork.

Featured in Forbes, Business Insider, Yahoo, Bloomberg, Financial Times, TechCrunch, and more. We are backed by General Catalyst, Sound Ventures, QED Investors, Google’s Gradient Ventures, Expa, and other investors who have financed iconic companies like YouTube, Substack, Twitch, Box, Hims, Instacart, and Lyft.

About the role:

As a Billing Specialist on the Member Operations team, you will own the billing side of the member lifecycle, from invoice questions and research all the way to the final offboarding billing work and disputes. You will work primarily in Stripe and Collective’s proprietary platform, resolving member billing questions, handling disputes and chargebacks, and making sure every refund and credit is accurate and follows policy.

You will also be the person who sees billing patterns first. When the same question or edge case keeps coming up, you will help us turn it into a clear policy or a better process, so the same situation gets the same answer no matter who handles it.

This role is ideal for someone who is detail-driven, comfortable with multi-step/system processes, and is able to explain a billing decision clearly to a member or a teammate.

Please note: This is a 12-month temporary, full-time position.

What you'll do

• Process refunds and credits in Stripe

• QA vendor invoices against internal records, owning the end-to-end process from issue flag to vendor contact/resolution

• Process offboarding requests, including final billing, subscription cancellations, and confirming nothing is left open in Stripe

• Manage member disputes and chargebacks end to end: gather evidence, submit responses in Stripe, track outcomes, and communicate status to internal partners

• Help inform billing policy by documenting recurring issues, edge cases, and trends: recommending changes to guidelines and guardrails

• Keep billing SOPs and documentation current as policies and processes change

• Partner with Finance, Operations, Sales, and Member Success to resolve billing issues and improve tooling

• Flag billing errors, unusual patterns, and potential revenue or member impact early

• Assist with ad hoc requests such as failed payment and past-due account reporting

What you'll bring

• 1+ years of billing, payments, accounts receivable, or customer billing support experience

• Experience in Stripe (subscriptions, refunds, credit notes, and disputes); experience with chargeback evidence/vendor dispute reason codes is a strong plus

• Sound judgment on when to follow a policy and when to escalate

• Understanding of complex subscription lifecycle operations, such as prorated upgrades/ downgrades or recurring/subscription billing schedules

• Clear written communication, including the ability to explain billing events and decisions in plain language

• Comfort working in a cross-platform, ticket-based environment (Zendesk, Jira, Salesforce)

• Ability to manage a high volume of requests and meet deadlines in a fast-paced environment

• A process-minded approach: you notice what keeps breaking and suggest a fix

• A team-oriented mindset with a high degree of professionalism, integrity, and accountability

What we offer:

• Remote-Friendly Environment: Flexibility to work from home while staying connected to the team.

• Health & Wellness: $200 quarterly reimbursement to support your well-being, eligible after 90 days of employment.

• Sick Time: 9 paid sick days per year.

• Comprehensive Coverage: Medical, dental, and vision insurance, eligible after 90 days of employment.

• Retirement: A 401k plan, eligible after 90 days of employment.

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