[Hiring] Manager of Billing Operations @Scale to Win, Inc

Role Description

The Manager of Billing Operations will oversee the day-to-day execution of the company’s billing, invoicing, and accounts receivable processes. This role ensures billing accuracy and timeliness while actively managing the collections lifecycle to optimize cash flow.

This is an execution-focused, highly collaborative role interfacing directly with customers, as well as internally with Customer Experience (CX), Sales, and Accounting. The ideal candidate is comfortable picking up the phone to resolve payment issues, partners effectively across teams to streamline customer support, and looks for opportunities to solve root-cause billing inefficiencies.

Core Responsibilities

• Billing & Invoicing Execution — 30%
  • Monitor Billing Workflows: Maintain daily oversight of end-to-end billing processes for recurring and usage-based products.
  • Invoice Generation: Execute weekly, one-off, ad-hoc, and manual invoicing as needed to support unique customer accounts or contractual setups.
  • Billing Accuracy: Monitor billing controls to ensure accuracy in invoice generation, proration, and usage calculations.
• Accounts Receivable & Collections Outreach — 25%
  • A/R Management: Oversee A/R aging reports and cash application activities to ensure accurate and timely posting of payments.
  • Proactive Collections: Drive the company's collections strategy, utilizing active outreach—including direct phone calls and targeted email escalations—to recover overdue funds.
  • Payment Negotiations: Directly engage with late-paying customers to negotiate payment plans, protecting company revenue while maintaining a professional customer relationship.
• Cross-Functional Coordination & CX Support — 15%
  • Sales & CX Collaboration: Partner closely with Sales and CX to coordinate collections efforts, ensuring internal alignment before executing account escalations.
  • Dynamic Operations Improvement: Assist on critical, time-sensitive ad-hoc projects, ensuring execution from conception to completion.
  • Customer Support Resolution: Work with customers and CX to resolve any specialized customer issues or requests.
  • Support Ticket Reduction: Educate customers on billing policies to proactively resolve complex billing questions and reduce inbound support ticket volume.
  • Contract Support: Support Sales with contract structuring considerations regarding standard billing and payment terms.
• Regulatory Compliance — 20%
  • Multi-State Registration: Monitor and support the company's legal and tax registration process in new states and ongoing compliance requirements, ensuring timely and accurate filings.
  • Coordination with Registered Agent Partner: Work with our vendor, CorpNet, to ensure ongoing filings are completed timely.
  • Nexus Monitoring: Manage the ongoing economic and physical nexus exposure across jurisdictions, flagging new filing obligations before they become compliance risks.
  • Filing Accuracy & Upkeep: Review and reconcile sales tax filings and remittances for accuracy, working with external accounting partners as needed.
• Accounting Coordination — 5%
  • Bad Debt Assessment: Partner closely with the Staff Accountant and Controller to make determinations around doubtful accounts and bad-debt allowances.
  • Month-End Support: Assist the Accounting team during the monthly close process related to revenue adjustments and reserves.
• Process Improvement — 5%
  • Root-Cause Problem Solving: Apply systems-thinking to identify gaps, errors, or friction points in billing workflows, proposing and implementing solutions to solve root-cause issues.

Qualifications

• 3+ years of experience in billing operations, accounts receivable, or corporate collections.
• Strong communication skills with a proven comfort level performing direct customer outreach (phone and email) for collections.
• Demonstrated ability to collaborate across teams (Sales, Customer Success, Accounting) to resolve complex billing challenges.
• A systems-thinking mindset with a desire to streamline workflows and fix repetitive operational errors.
• Familiarity with accounting principles (GAAP) related to A/R and bad debt is a plus.

Travel Expectations

This role may require occasional travel to support client meetings, campaign events, trainings, or company gatherings. Travel expectations will vary based on client needs and campaign cycles, particularly during peak election seasons.

Secure Handling of Sensitive Data

This role may frequently handle sensitive company and personal data. Given this, staff must ensure all financial, billing, and sensitive vendor or customer data is processed in a private, distraction-free environment to maintain high accuracy and security.

Salary and Benefits

• $80,000 yearly salary (base). As part of our commitment to equity, salaries are non-negotiable.
• This role may be eligible for a discretionary bonus as determined by the company in its sole discretion.
• 401k matching up to 6% after a provisional period.
• Ten paid company holidays, two floating holidays, and a week and a half-long holiday break at the end of the year.
• Generous paid vacation (up to 24 days a year with time accrued monthly); paid sick leave; paid short-term medical, caregiver, bereavement, and other personal leave.
• 16 weeks of paid parental leave and an additional 4 weeks of part-time, fully-paid flex time. This is available to all new parents of any gender, including adoptive parents.
• Fully-paid premium, $0 deductible, top-notch medical insurance, as well as dental and vision insurance, for you and your dependents.
• Remote working with flexible working conditions, a stipend to support your home office setup, and access to a company computer.
• Every employee is invited to donate 25,000 free texts to a non-profit of their choice each year.
• To support continued professional growth and development, Scale to Win offers each employee an annual $2,000.00 stipend towards achieving your professional development goals.

Interview Process

• Submit application
• Initial Screening Interview
• Hiring Manager interview
• Hiring Exercise + Panel Interview
• Co-CEO Meet & Greet
• Reference check

The position will be open until filled, and applications will be reviewed on a rolling basis. Applicants must be currently authorized to work in the United States on a full-time basis. At this time, we’re unable to sponsor or take over sponsorship of employment visas.

Interview Accommodations

Scale to Win is committed to providing all candidates a respectful and inclusive interview process. If you require any accommodations to fully participate in the interview process—such as alternative formats, extended time, assistive technology, or other support—please let us know.

Scale to Win is an equal opportunity employer. In keeping with our beliefs and goals, no applicant will face discrimination or harassment based on race, color, ancestry, national origin, religion, age, gender, marital domestic partner status, sexual orientation, gender identity, disability status, or veteran status.