Bask Health is looking for a Billing Operations Specialist to take full ownership of our internal billing systems and customer invoicing workflows. In this role, you will use Stripe to ensure billing is accurate, timely, and compliant as we scale our revenue operations and billing automation.
What You'll Do
- Own and operate all Stripe workflows end-to-end, including configuring invoice templates, rules, and delivery schedules.
- Monitor daily payment activity, track failed charges, resolve billing issues, and follow up on past-due accounts.
- Partner with Customer Success to onboard new customers 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 CRM data to ensure 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 the Finance team.
- 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.
What We're Looking For
- A Stripe expert, especially with Stripe Invoicing; you have configured invoice settings, templates, and workflows directly in the platform.
- 2+ years of experience in billing, accounts receivable, or revenue operations at a SaaS or healthcare company.
- Proven ability to chase and close unpaid invoices; you are proactive and persistent with collections.
- Highly detail-oriented with strong analytical, investigative, and organizational skills.
- Experience with 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 for frequent emails to customers and internal teams.
Nice to Have
- Familiarity with HIPAA-compliant systems, telehealth workflows, or B2B SaaS pricing models.
Technical Stack
- Stripe
- Stripe Invoicing
Team & Environment
You will work cross-functionally with Customer Success, Finance, Product, and Engineering. Our team is driven and collaborative, focused on enabling clinical founders and digital health startups to move fast.
Work Mode
This is a remote-first position.
