AR and Billing Specialist

Who We Are

Rilla is the leading virtual ride-along software for outside sales. We empower home improvement professionals, home builders, property managers, and other salespeople who meet customers face-to-face. Our mobile app records conversations, and our AI automatically transcribes and analyzes them to help improve sales performance.

Our vision is to bring conversation intelligence from Zoom meetings and call centers to more than 10 million salespeople who work offline. We are one of the fastest-growing startups in the world and are backed by Crystal Huang of Google Ventures and Byron Deeter of Bessemer Venture Partners, a top Cloud investor. We are a Cloud 100 Rising Star company.

The Role

We’re hiring an AR and Billing Specialist to join Rilla’s Finance team. You’ll own billing operations end to end—from invoicing and collections to cash flow reporting and reconciliation. This includes proactively reaching out to customers with overdue balances to resolve outstanding invoices and keep cash moving. You’ll work closely with Finance, Operations, Customer Success, and Sales to tighten up systems and maintain visibility into business performance.

Who You Are

• A customer-obsessed individual who cares about delighting clients and solving their pains, not vanity metrics.
• An infinite learner who seeks continuous growth and avoids complacency.
• A team player who values feedback and collective growth.
• Unafraid of failure—willing to take risks and view setbacks as learning opportunities.
• Affinity for the unconventional—comfortable challenging conventional wisdom and exploring new ideas.
• Extremely focused—able to prioritize time and resources for maximum efficiency.

What You'll Do

• Partner with Sales, Customer Success, and Engineering to ensure customer billing is set up correctly based on contract terms
• Prepare, review, and distribute AR invoices through billing platforms and customer portals
• Proactively reach out to customers with overdue balances to drive collections and resolve outstanding invoices
• Maintain meticulous collections documentation and send timely customer account statements
• Ensure accurate cash application of payments and keep AR ledgers clean
• Support billing portal registrations and compliance requirements, coordinating with legal, customer success, and insurance teams as needed
• Identify and implement process improvements to streamline billing and AR operations

What We Need

• 1–2+ years of experience in billing, accounts receivable, or a related finance/operations role
• Familiarity with billing platforms and customer invoicing portals
• Strong attention to detail and ability to manage a high volume of accounts
• Clear, professional communication skills — especially when following up on overdue balances
• Clear, direct, and not afraid to speak up with ideas or flag risks
• Entrepreneurial spirit and willingness to roll up sleeves in a fast-paced, dynamic environment
• Bachelor’s degree in Accounting, Finance, Economics, or a related field preferred, but not required

Don’t Work Here

Please don’t apply if you’re not excited about:

• Working ~70 hours a week in person with ambitious people
• Building a generational company with the intensity and speed that requires
• Owning critical financial processes that directly impact growth and customer experience

Compensation & Benefits

• Salary: $87,000 – $100,000/year (with room to go higher for exceptional candidates; competitive with other offers)
• Medical, dental, and vision insurance
• 401(k) retirement plan
• Breakfast, lunch, dinner, and supplementary food and drink — 6x a week
• Gym membership
• Commuter benefits
• Relocation assistance
• Paid time off (take what you need, not accrual-based)
• $1,000 stipend for learning and personal growth
• Tech equipment