Full-Time

Mailroom Operations Associate

Updated on 9/3/2026

Checkbook

Checkbook

51-200 employees

Digital payments platform replacing checks

Compensation Overview

$50k - $60k/yr

+ Bonus + Equity + Mileage reimbursement

San Mateo, CA, USA

In Person

Mileage reimbursement is provided for required driving.

Category
Warehouse & Fulfillment (1)

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Requirements
  • A valid driver's license, a clean driving record, and a vehicle to operate.
  • Skill in troubleshooting and resolving issues efficiently.
  • Meticulous and thorough attention to detail for identifying small errors.
  • A solid technical background through education or experience, with the ability to quickly learn new tools and technologies.
  • Clear and effective communication with technical and non-technical team members and clients.
  • The ability to adjust to new processes and technologies as needed.
  • The ability to lift up to 50 pounds with or without accommodations.
Responsibilities
  • Manage, operate, set up, and fine-tune printing, mailing, and bindery equipment to ensure print jobs meet quality standards.
  • Track and manage machine supplies, anticipate needs, prevent shortages, and maintain operational continuity.
  • Mail checks and coordinate with logistics partners to ensure proper delivery.
  • Resolve communication challenges by clarifying complex instructions and addressing misunderstandings.
  • Create and improve operational processes to increase efficiency and effectiveness.
  • Troubleshoot operational issues to keep operations moving forward.
Desired Qualifications
  • A background in financial technology is a plus but not required.

Checkbook.io provides a digital payments platform for businesses to send and receive instant payments via email or phone, replacing paper checks and expensive transfers. It supports mass payments via CSV uploads and integrates with accounting software like Sage-Intacct, AccountingSeed, QuickBooks, and Moneypod; recipients do not need a Checkbook account. The platform includes an integrated accounting dashboard with live payment tracking for real-time visibility. Its goal is to offer a simple, affordable, and transparent digital payments option that reduces payment friction and costs (under $1 per transaction).

Company Size

51-200

Company Stage

Series A

Total Funding

$22.4M

Headquarters

San Mateo, California

Founded

2015

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Simplify Jobs

Simplify's Take

What believers are saying

  • August 2024 expansion drew rental, legal, government, and banking demand.
  • January 2026 Visa Direct collaboration expands realtime disbursements across millions of endpoints.
  • Eisen partnership targets CFPB-driven offboarding refunds, a painful compliance use case.

What critics are saying

  • Visa, J.P. Morgan, and banks can disintermediate Checkbook within 18 months.
  • Digital-check demand depends on legacy check volumes, which keep shrinking annually.
  • 2026 leadership changes signal execution risk after only $10 million total funding.

What makes Checkbook unique

  • Single API spans ACH, RTP, FedNow, Visa Direct, checks, and cards.
  • J.P. Morgan Payments network access embeds Checkbook into corporate disbursement workflows.
  • White-labeled payments plus no-recipient-signup onboarding reduces payee friction and integration overhead.

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Benefits

Health Insurance

Dental Insurance

Vision Insurance

401(k) Retirement Plan

Company Equity

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

0%

2 year growth

4%
The Fintech
Apr 15th, 2025
Checkbook Recognized as a Leader in Digital Payment Solutions by Frost & Sullivan

Checkbook, a leading innovator in digital payment solutions, has been named a leader in B2B Digital Payments by Frost & Sullivan in B2B Digital Payment Systems 2025.

Yahoo Finance
Mar 19th, 2025
In This Article:

PayPal Holdings experienced a 1% price increase last week, a move that coincided with Checkbook's launch of new payment rails.

PYMNTS
Aug 22nd, 2024
Checkbook Expands Payment Operations Amid Shift From Paper Checks

Payments solution provider Checkbook has expanded its payment operations. The company announced this expansion in a Thursday (Aug. 22) news release, saying it marked a milestone in “streamlining check and payment operations for a variety of business use cases in the U.S.”. According to the release, Checkbook has seen a surge in interest from industries like the rental, legal, government and banking sectors, spotlighting a rising demand for efficient and streamlined payment operations

PYMNTS
May 17th, 2024
Eisen And Checkbook Partner To Streamline Disbursements By Financial Institutions

Eisen and Checkbook partnered to help financial institutions streamline payment disbursements and ensure compliance with consumer protection regulations. The companies’ new Disbursement Hub is designed to help financial institutions meet the challenge of the evolving regulatory landscape around account closures and fund disbursements, according to a Thursday (May 16) press release. “Our strategic partnership is a crucial step to help financial institutions navigate the complexities of compliant offboarding and consumer protection, without dedicating an entire team to manage the process,” Eisen CEO Allen Osgood said in the release

Business Wire
May 16th, 2024
Eisen And Checkbook Revolutionize Payment Disbursements With Launch Of Disbursement Hub

SAN MATEO, Calif.--(BUSINESS WIRE)--In response to the evolving regulatory landscape surrounding account closures and fund disbursements, leading financial technology companies Eisen and Checkbook have joined forces to introduce Disbursement Hub—a groundbreaking solution designed to streamline payment disbursements and ensure compliance with consumer protection regulations. The Consumer Financial Protection Bureau (CFPB) has heightened its enforcement efforts, placing a spotlight on the prompt handling of refunds when accounts are closed. Failure to act quickly can result in significant penalties, making it imperative for financial institutions to align their processes with regulatory requirements. Disbursement Hub offers a comprehensive solution to assist institutions in navigating the complexities of account closures and fund disbursements efficiently. Eisen is building the future of account offboarding across the three critical phases of closing customer accounts—Outreach, Disbursement, and Escheatment—with a focus on meticulous attention to detail and adherence to regulatory timelines. Eisen chose Checkbook to power Disbursement Hub to replace manual workflows, reduce errors, save time, and ensure timely compliance with regulatory guidelines