---
title: 'Mailroom Operations Associate at Checkbook'
canonical: 'https://feeny.ai/job/mailroom-operations-associate-checkbook-san-mateo-2sygwnfgst64'
type: 'job'
last_seen: '2026-09-09'
---

# Mailroom Operations Associate at Checkbook

- **Company:** Checkbook
- **Location:** San Mateo, CA
- **Posted:** 2025-11-18
- **Last confirmed live:** 2026-09-09
- **Apply:** https://job-boards.greenhouse.io/checkbook/jobs/4984745007

## Job description

About Us:

Checkbook enables businesses to access the speed, flexibility and cost savings of digital payments, with the familiarity and simplicity of paper checks. By providing businesses an on-ramp from paper to digital payments, we can effectively onboard customers at any stage of their digital transformation process.

The Role: Are you someone who loves the smell of fresh paper and enjoys solving technical puzzles? Do you find satisfaction in mastering a process and making it your own? If so, we have the perfect opportunity for you! As a Mailroom Operations Associate, you’ll be the superhero behind our daily paper check operations. You’ll take charge of ensuring that everything runs smoothly and get to define and refine the process to make it even better. This role isn’t just about maintaining the status quo—it’s about continuously pushing the envelope, solving problems, and making a real impact. If you’re up for the challenge, this is the perfect place to put your skills to the test!

Responsibilities:

- Manage our high-tech printing, mailing, and bindery equipment. You'll not only operate and set up these systems but also fine-tune them to perfection, ensuring that every print job meets our high standards and that everything runs like clockwork.
- Take full ownership of tracking and managing machine supplies. It’s up to you to anticipate needs, prevent shortages, and keep everything running smoothly—no small feat when you’re juggling multiple demands.
- Handle the vital task of mailing checks, coordinating with our logistics partners for flawless execution. You’ll be the last line of defense in ensuring these important documents reach their destinations without a hitch.
- Navigate and resolve communication challenges with finesse, whether it’s clarifying complex instructions or smoothing out misunderstandings. Your ability to keep everyone on the same page will be key to maintaining our high standards of service.
- Not only will you handle the daily operations, but you’ll also have the opportunity to create and improve the process to make it more efficient and effective.
- Sometimes things go wrong, and that’s where your technical skills come in. You’ll troubleshoot any issues that arise, ensuring that our operations keep moving forward.

Qualifications:

- Must have a valid driver’s license, clean driving record and vehicle to operate.
- You enjoy a good challenge and are skilled at troubleshooting and resolving issues efficiently.
- You’re meticulous and thorough, with a keen eye for catching even the smallest errors.
- You have a solid technical background, whether through education or experience and can quickly learn new tools and technologies.
- You’re able to communicate clearly and effectively with both technical and non-technical team members and clients.
- You’re flexible and open to change, able to adjust to new processes and technologies as needed.
- Ability to lift up to 50 lbs with or without accommodations.
- A background in fintech is a plus, but not required.

Benefits & Perks:

- Base salary 50-60k
- Insurance (Medical, Dental, Vision, LTD, and a variety of other programs)
- 401k
- Equity
- Catered meals (in office)
- Mileage Reimbursement

Variable Base + Bonus + Equity (based on experience)

*Equal Opportunities Employment Statement* It is our policy to provide equal opportunities for all employees in relation to recruitment, training and promotion. Decisions in these areas will be made only by reference to the requirements of the job and shall not be influenced by any consideration of age, disability, gender reassignment, marriage or civil partnership, pregnancy or maternity, race (including color, nationality and ethnic and national origin), religion or belief, sex or sexual orientation.

If you are interested in applying for employment and need special assistance or an accommodation to use our website to apply for a position, please contact us directly.

** To all recruitment agencies: Checkbook.io does not accept unsolicited agency resumes. Please do not forward resumes to Checkbook employees. Checkbook is not responsible for any fees related to unsolicited resumes and will not pay fees to any third-party agency or company **

## About Checkbook

## Company Overview
- **One-liner**: Checkbook is an API-first digital payments platform that enables businesses to disburse payments at scale across all major US payment rails, requiring only a recipient’s name and email.
- **Entity Type**: Private (Series A)
- **Headquarters**: San Mateo, California, USA
- **Founded**: 2015
- **Founders**: PJ Gupta (former Chief Network Architect at Visa)

## Core Business
- **Primary industry**: Financial Services / Payment Infrastructure
- **Target customers**: B2B – insurance carriers, property TPAs, marketplaces, financial services companies, enterprises of all sizes
- **Mission**: To simplify payment disbursements by eliminating paper checks and the burden of collecting sensitive banking data, enabling businesses to send funds efficiently, securely, and at scale.

## Products & Services
- **Digital Disbursement Platform (API)**: A single RESTful API that connects businesses to all major US payment rails – ACH, Real-Time Payments (RTP), FedNow, digital checks, paper checks, push-to-card (Visa Direct), virtual cards, Zelle, Venmo, PayPal, and wire transfers. Payments are initiated with only the recipient’s name and email; no enrollment or banking data required. Includes batch workflows, integrations with QuickBooks Online and AccountingSeed, and a white-label dashboard. [checkbook.io](https://checkbook.io/)
- **sureti (Insurance Claims Payment Solution)**: Acquired in January 2025, sureti is an end-to-end payment platform purpose-built for the property insurance claims ecosystem. It eliminates multi-party check issuance, provides geospatial fund release substantiation, and integrates with mortgage lenders and lienholders. [insurtechlist.com](https://insurtechlist.com/companies/checkbook/)
- **Virtual Cards & Push-to-Card**: Enable instant disbursements to Visa/MasterCard debit cards, including global push-to-card via Visa Direct. [checkbook.io](https://checkbook.io/)
- **Digital Wallet Transfers**: Support for PayPal and Venmo disbursements, launched in March 2025. [linkedin.com](https://www.linkedin.com/company/checkbook)

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed
- **Key Metric**: Annual Revenue of USD 6.0M (LinkedIn estimate) | Total Funding of USD 24.15M across multiple rounds, including a USD 10M Series A led by MassMutual Ventures (Nov 2021) and participation from Plug and Play Tech Center. [linkedin.com](https://www.linkedin.com/company/checkbook) | [tracxn.com](https://tracxn.com/d/companies/checkbook/__v1UqugMD4B1PL0djG6sbcZe-24K2FiacnQE58ZnQ5-s)
- **Notable Investors/Partners**: MassMutual Ventures, Plug and Play Tech Center, J.P. Morgan, Visa
- **Growth Signals**: 
  - Acquired sureti (Jan 2025) to deepen insurance vertical capabilities.
  - Launched global push-to-card payments powered by Visa Direct (Feb 2025).
  - Integrated PayPal and Venmo digital wallet transfers (Mar 2025).
  - Recognized as a Leader in B2B Digital Payment Systems by Frost & Sullivan (Apr 2025).
  - Won two TSG Real Transaction Metrics Awards (2025).
  - Over 98,000 merchants on the platform. [insurtechlist.com](https://insurtechlist.com/companies/checkbook/)
  - Employee count grew from 33 (LinkedIn) to 52 (Tracxn, May 2026), indicating scaling.

## Competitive Advantages
- **Single API for all US payment rails**: No other processor offers such a unified, easy-to-integrate solution covering ACH, RTP, FedNow, checks, cards, and digital wallets.
- **No recipient enrollment required**: Payments can be sent knowing only name and email – drastically reducing friction compared to platforms that require bank account or card details upfront.
- **White-label customization**: Full control over user experience, emails, and branding – ideal for marketplaces and platforms.
- **Deep insurance vertical expertise**: The sureti acquisition gives Checkbook a specialized, end-to-end solution for property claims disbursements, including geospatial validation and lender integration.

## Strategic Focus
- **Insurance vertical expansion**: Leveraging sureti to become the go-to payment platform for property and casualty insurance carriers, TPAs, and catastrophe management teams.
- **Global push-to-card and wallet integrations**: Expanding into real-time international disbursements via Visa Direct and popular digital wallets (PayPal, Venmo) to serve a broader range of payout use cases.
- **Developer experience and ease of integration**: Continuing to invest in API documentation, pre-built integrations, and a 10-minute setup promise to attract more developers and platforms.

## Why Work Here
- **Culture**: “Work hard – play hard” environment with a close-knit, “all for one, one for all” team. The company emphasizes transparency, specificity over corporate speak, and mutual support. [greenhouse.io](https://job-boards.greenhouse.io/checkbook)
- **Work Model**: HQ in San Mateo, CA with multiple office locations in the area. Some roles (e.g., Internship Talent Pool) list “HQ or Remote” – indicating flexibility. [linkedin.com](https://www.linkedin.com/company/checkbook)
- **Engineering Culture**: API-first, developer-friendly platform; engineers work on cutting-edge payment rails, integrations, and infrastructure.
- **Perks & Growth**: Fast-growing company (recent funding, acquisition, awards) offering exposure to fintech innovation and career advancement. Employee rating of 4.3/5 on LinkedIn, with high marks for career development (4.4) and culture (3.9). [linkedin.com](https://www.linkedin.com/company/checkbook)
- **Open Roles**: Currently hiring for Mailroom Operations Associate and an Internship Talent Pool – ideal for those looking to get hands-on in a growing fintech startup. [greenhouse.io](https://job-boards.greenhouse.io/checkbook)

## Sources
1. [greenhouse.io](https://job-boards.greenhouse.io/checkbook) – Careers page and culture description
2. [checkbook.io](https://checkbook.io/) – Product details, API documentation, and integrations
3. [linkedin.com](https://www.linkedin.com/company/checkbook) – Company overview, financials, employee count, funding, reviews, and recent news
4. [tracxn.com](https://tracxn.com/d/companies/checkbook/__v1UqugMD4B1PL0djG6sbcZe-24K2FiacnQE58ZnQ5-s) – Funding history, competitor landscape, and employee count
5. [insurtechlist.com](https://insurtechlist.com/companies/checkbook/) – Detailed product description, insurance vertical focus, and acquisition details

## Other roles at Checkbook

- [Checkbook Internship Talent Pool](https://feeny.ai/job/checkbook-internship-talent-pool-checkbook-san-mateo-pzjx5fgv1f3e) — San Mateo, CA
- [Checkbook Talent Pool](https://feeny.ai/job/checkbook-talent-pool-checkbook-hq-v8zg0wnzaq2b) — Hq, OR