AR and Billing Specialist

Rilla; New York (NY); On-site; USD 87,000 - 100,000; Full time

Benefits offered by this job

Medical, dental and vision insurance

401(k) retirement plan

Wellness benefits

Commuter benefits

Relocation assistance

Paid time off (not accrual-based)

Learning stipend

Tech equipment

Job summary

Rilla, a leading virtual ridealong software provider for outside sales, is hiring an AR and Billing Specialist in New York. You will own end-to-end billing operations, from invoicing to collections, and work with Finance, Operations, Customer Success, and Sales to ensure accurate cash flow and timely reporting.

You’ll thrive as a customer-obsessed, proactive learner who values feedback and can navigate a fast-paced startup environment.

Qualifications

• 1-2+ years of experience in billing, accounts receivable, or related finance/ops role.
• Familiarity with billing platforms and customer invoicing portals.
• Strong attention to detail and ability to manage high volume of accounts.
• Clear, professional communication—especially following up on overdue balances.
• Entrepreneurial mindset and willingness to work hands-on in a fast-paced environment.

Responsibilities

• Partner with Sales, Customer Success, and Engineering to ensure customer billing is set up correctly per 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.
• 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 with legal, customer success, and insurance teams.

Skills

Billing experience

Attention to detail

Communication skills

Team player

Entrepreneurial mindset

Education

Bachelor’s degree in Accounting/Finance/Economics or related

Tools

Billing platforms

Invoicing portals

Job description

Who We Are Rilla’s the leading virtual ridealong software for outside sales. Think home improvement, home builders, property managers, and other sales people who talk to customers face to face.

Who We Are Rilla’s the leading virtual ridealong software for outside sales. Think home improvement, home builders, property managers, and other sales people who talk to customers face to face. Sales reps talk, our mobile app records their conversations, and our AI automatically transcribes and analyzes their conversations to help them improve their sales. Our vision is to bring the power of conversation intelligence from the Zoom meeting and the call center to the more than 10M sales people who work offline. We are one of the fastest growing startups in the world right now and in history. We’re backed by Crystal Huang of Google Ventures, and Byron Deeter (one of the best investors of all time) from Bessemer Venture Partners, the top Cloud investor in the world. And we’re 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. That 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 obsessive. Someone who deeply cares about delighting clients and solving their pains, not about vanity metrics.
• An infinite learner. You are always looking to learn more and learn faster. You feel uneasy when you get complacent, and you’re constantly seeking discomfort.
• A team player. You love giving and receiving feedback and learning and growing as a team.
• Unafraid of failure. You take risks. You see failure as an opportunity to learn, grow, and be better the next time. In a weird way, you trick your brain into being excited when you fail because it means you get a new opportunity to learn more.
• Affinity for the unconventional. You get a kick out of rejecting conventional wisdom. And you’re not afraid to try weird, crazy, and quite possibly stupid ideas.
• Extremely focused. You practice extreme focus in everything you do. You’re always looking to prioritize your 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 and work hands-on in a fast-paced, dynamic environment.
• Bachelor’s degree in Accounting, Finance, Economics, or 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
• Wellness / Gym Benefits
• Commuter benefits
• Relocation assistance
• Take what you need, paid time off, not accrual-based
• $1,000 stipend for learning and personal growth
• Tech equipment

Compensation Range: $87K - $100K