How to apply for Manager of Billing Operations

About Scale to Win

Scale to Win is a fully-remote political tech company founded in 2020 by organizers from major Democratic presidential campaigns. It builds texting and calling tools used by over 3,000 progressive campaigns and organizations. The company is transitioning from external bookkeeping to an in-house, GAAP-compliant accounting function, so this is a chance to help build processes from the ground up.

About the role

The Manager of Billing Operations owns the day-to-day billing, invoicing, and accounts receivable work. You will ensure invoices go out accurately and on time, manage collections to improve cash flow, and work directly with customers plus internal teams in Customer Experience, Sales, and Accounting. This is an execution-focused role, not a strategy-only position.

A typical day

A typical day might involve reviewing new invoices for accuracy, sending them out, following up on overdue accounts, and answering billing questions from customers. You would also coordinate with Customer Experience and Sales on account issues and with Accounting on reconciliation. Because the company is building its in-house accounting function, you may spend time documenting or improving billing processes.

Who Scale to Win is looking for

• Has hands-on experience running billing, invoicing, and accounts receivable in a B2B or SaaS environment, including collections follow-up.
• Is comfortable working directly with customers on billing questions, payment issues, and overdue balances.
• Can operate in a remote, fast-moving company where processes are still being built and documented.
• Has worked cross-functionally with sales, customer success, and accounting teams, and can communicate clearly in writing.

Tips for this application

• In your resume, quantify billing volume you have handled: number of invoices per month, average AR balance, days sales outstanding, or collection rates.
• Name the billing or accounting systems you have used (e.g., QuickBooks, Stripe, NetSuite, Bill.com) because Scale to Win is moving to an in-house GAAP setup and will care about tool familiarity.
• Mention any experience with political campaigns, unions, nonprofits, or mission-driven clients, since Scale to Win serves Democratic and progressive organizations.
• Address remote work directly: give an example of how you have managed collections or resolved billing issues without in-person contact.
• Keep your cover letter short and concrete. Focus on billing execution and collections results, not on why you like politics.

What to cover in your cover letter

Describe a specific billing or collections process you improved and the measurable result. Explain how you have handled a difficult customer payment conversation. Show you understand the difference between billing accuracy and collections timing. State why you want to work at a company building its accounting function from scratch.

Research before applying

• Read about Scale to Win Text and Scale to Win Dialer on their website so you understand what clients are being billed for.
• Look up the company's clients, such as the Biden-Harris campaign, DNC, Working Families Party, AFL-CIO, UFCW, MoveOn, and For Our Future, to understand the customer base.
• Find out what billing or accounting software Scale to Win currently uses or plans to use, and be ready to discuss your experience with similar tools.
• Check if the company has posted anything about its transition from external bookkeeping to in-house accounting, since this role is part of that change.

Likely interview topics

Based on the job description, expect questions about:

• Walk through your process for generating and sending invoices accurately and on time.
• How do you handle a customer who is past due but disputes the invoice?
• What metrics do you track to monitor accounts receivable health, and how have you improved them?
• How would you build billing and collections workflows from scratch in a remote company?
• How do you coordinate with sales and customer experience teams when a billing issue affects a client relationship?

Common mistakes to avoid

• Focusing only on invoicing and ignoring collections. This role explicitly includes managing the collections lifecycle and cash flow.
• Writing a generic cover letter that does not mention billing, accounts receivable, or the company's political tech client base.
• Assuming the role is strategic or managerial in the people-management sense. The description calls it execution-focused, so emphasize hands-on work.