Billing Operations Specialist

Bask Health is a fast-growing SaaS company on a mission to power the next generation of telehealth businesses. We help healthcare entrepreneurs launch, manage, and scale their virtual care services through modern infrastructure, easy-to-use tools, and expert operational support.

We’re a driven and collaborative team focused on enabling clinical founders and digital health startups to move fast. If you're excited by the intersection of healthcare and technology, and love solving operational problems at scale, we’d love to hear from you.

We're looking for a Stripe Billing & Revenue Operations Lead with deep Stripe expertise, including Stripe Invoicing, to take full ownership of our internal billing systems and customer invoicing workflows. You’ll be the go-to person for everything Stripe — 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.

• Own and operate all Stripe workflows end-to-end, including Stripe Invoicing: configure invoice templates, rules, and delivery schedules
• Monitor payment activity in Stripe daily — track failed charges, resolve billing issues, and follow up on past-due accounts until closed
• 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

• Stripe Expert, especially Stripe Invoicing: you’ve configured invoice settings, templates, and workflows directly in the Stripe platform
• 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

• Stripe 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
• Internal teams rely on you for Stripe expertise and revenue process improvements