[Hiring] Billing Operations Specialist @Bask Health

Role Description

We're looking for a Billing & Revenue Operations Lead to take full ownership of our internal billing systems and customer invoicing workflows. You’ll be the go-to person for everything — configuring invoices, managing subscriptions, chasing unpaid accounts, and scaling billing infrastructure.

You’ll work cross-functionally with Customer Success, Finance, Product, and Engineering to ensure billing is accurate, timely, and compliant. This is a highly operational and strategic role where you'll help scale our revenue operations and improve billing automation across the company.

What You’ll Do

• Monitor payment activity daily — track failed charges, resolve billing issues, and follow up on past-due accounts until closed
• Own and operate all Stripe workflows end-to-end, including Stripe Invoicing: configure invoice templates, rules, and delivery schedules
• Partner with Customer Success to ensure new customers are correctly onboarded with accurate billing terms and pricing
• Generate and send recurring invoices, confirm payments, and ensure proper tax and pricing structures are applied
• Maintain and audit Stripe and internal CRM data, ensuring 100% billing accuracy across platforms
• Identify and resolve customer disputes, subscription edge cases, charge errors, and billing escalations
• Assist in scaling billing automation, Stripe tooling, documentation, and compliance workflows
• Support revenue recognition and monthly reporting for Finance
• Collaborate with Product and Engineering on platform-generated billing events and complex subscription logic
• Ensure compliance with HIPAA, PCI, and other regulatory standards in billing and payments

Qualifications

• 2+ years of experience in billing, AR, or revenue operations at a SaaS or healthcare company
• Proven ability to chase and close unpaid invoices — you’re proactive and persistent with collections
• Highly detail-oriented with strong analytical, investigative, and organizational skills
• Experienced in high-volume recurring billing, subscription changes, and charge disputes
• Able to work cross-functionally and independently in a fast-paced, remote-first startup environment
• Clear and professional written communication skills (you’ll be emailing customers and internal teams often)

Nice to have

• Familiarity with HIPAA-compliant systems, telehealth workflows, or B2B SaaS pricing models
• SQL
• Excel

What Success Looks Like in This Role

• Invoicing is fully optimized and running smoothly across all accounts
• Past-due accounts are followed up on immediately and resolved within target timelines
• Stripe billing is clean, automated, and transparent across teams
• You’re the first to spot a billing issue—before the customer does