Billing Operations Specialist
About The Position
Bask Health is a fast-growing SaaS company that provides infrastructure, tools, and operational support to telehealth businesses. The Billing Operations Specialist role owns the company’s internal billing systems and customer invoicing workflows, including invoice configuration, subscription management, collections, and billing infrastructure. The role works across Customer Success, Finance, Product, and Engineering to ensure billing is accurate, timely, and compliant, while improving revenue operations and billing automation. The successful candidate will monitor payment activity, operate Stripe workflows, support customer onboarding and recurring invoicing, maintain billing data, resolve disputes and escalations, and assist with revenue recognition and monthly financial reporting. The position also contributes to billing automation, documentation, compliance workflows, and platform-generated billing logic. Success in the role means invoicing runs smoothly across accounts, overdue balances are addressed promptly and resolved within target timelines, Stripe billing is clean and transparent, and billing issues are identified proactively.
Requirements
- At least 2 years of experience in billing, accounts receivable, or revenue operations at a SaaS or healthcare company.
- Demonstrated ability to pursue and close unpaid invoices, with a proactive and persistent approach to collections.
- Strong attention to detail, analytical and investigative skills, and organizational abilities.
- Experience with high-volume recurring billing, subscription changes, and charge disputes.
- Ability to work cross-functionally and independently in a fast-paced, remote-first startup environment.
- Clear and professional written communication skills for frequent communication with customers and internal teams.
Nice To Haves
- Familiarity with HIPAA-compliant systems, telehealth workflows, or B2B SaaS pricing models.
- SQL.
- Excel.
Responsibilities
- Monitor payment activity daily, track failed charges, resolve billing issues, and follow up on past-due accounts through resolution.
- Own and operate Stripe workflows end to end, including configuring invoice templates, rules, and delivery schedules.
- Partner with Customer Success to ensure new customers are onboarded with accurate billing terms and pricing.
- Generate and send recurring invoices, confirm payments, and ensure appropriate tax and pricing structures are applied.
- Maintain and audit Stripe and internal CRM data to ensure billing accuracy across platforms.
- Identify and resolve customer disputes, subscription edge cases, charge errors, and billing escalations.
- Assist with 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.
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What This Job Offers
Job Type
Full-time
Career Level
Mid Level
Education Level
No Education Listed
