Manager of Billing Operations

Scale to Win is a fully-remote, progressive, political tech company founded in 2020 by organizing leaders from the Biden/Harris, Bernie 2020, Warren 2020, Bernie 2016, and Hillary for America Presidential campaigns. Our product offerings include Scale to Win Text, our “all-in-one” shortcode and longcode texting tool, and the Scale to Win Dialer, a predictive calling tool. Scale to Win also offers turnkey “We Text” services, where our team builds text campaigns, sends messages, collects data, and ensures compliance on behalf of clients.

We work with more than 3,000 Democratic and progressive campaigns and organizations, driving change. Current and past clients include the Biden-Harris campaign, the Democratic National Committee, the Working Families Party, the AFL-CIO, UFCW, MoveOn, and For Our Future.

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 .

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 — 35%

• 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 — 20%

• 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 .

Accounting Coordination & Compliance — 10%

• 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 .

• 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

This role description is intended to convey information essential to understanding the scope of the position and is not an exhaustive list of skills, efforts, duties, responsibilities, or working conditions associated with it. Other duties may be assigned as needed to support the success of the team and organization.

We are a remote-first team that gathers in person a couple of times a year for team building and alignment. This role requires roughly 10% travel, primarily for offsites and critical external meetings with partners or customers.

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. To protect the Company’s intangible assets and PII, this work must not be performed in public or unsecured settings in accordance with all company data access policies and applicable laws.

• $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.

• 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. You can request accommodations by emailing [email protected].

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. Above and beyond discrimination/harassment based on “protected categories,” Scale to Win also strives to prevent other, subtler forms of inappropriate behavior (e.g., stereotyping) from ever gaining a foothold. Whether blatant or hidden, barriers to success have no place at Scale to Win.