Chief of Staff

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San Mateo, CA
In-Office
eCommerce • Payments • Financial Services
The Role

About Us:
Checkbook is a leading FinTech company revolutionizing the way businesses send and receive digital payments. Our innovative platform enables businesses to send and receive checks securely and instantly without the need for physical checks or any manual intervention. We are dedicated to providing simple, reliable, and cost-effective payment solutions to our clients. 

The Role:
We are seeking a dynamic and experienced individual to join our team as a Chief of Staff. Reporting directly to the Founder/CEO, this role offers increasing autonomy over time and a unique opportunity to shape both the operational and strategic decisions of the entire company. As the go-to person for all requests to the Founder/CEO, you will play a pivotal role in facilitating communication and collaboration across multiple functions, including Product, BD/Sales, Growth-Marketing, Customer Service, and Operations.

Key Responsibilities:

  • Work closely with the Founder/CEO, gaining a deep understanding of their daily routine, task prioritization, and scheduling
  • Build rapport with the entire team and establish a regular cadence of interactions
  • Serve as a knowledgeable liaison, managing the CEO's appointments and effectively communicating with internal and external stakeholders
  • Collaborate with senior management to ensure efficient communication and prioritize their interactions with the CEO
  • Contribute to shaping the company's culture, operations, and customer-centric approach
  • Collaborate with product and engineering teams to understand customer needs and drive product development
  • Partner with the Marketing and PR teams to educate and expand our customer base

Requirements for Success:

  • Ability to thrive in a fast-paced environment with limited information, making real-time decisions and effectively articulating trade-offs to the CEO
  • Excellent time management skills, with flexibility to work varied hours and handle intense workdays
  • Resilience and composure under pressure, maintaining a calm demeanor in challenging situations
  • Strong leadership skills, with a proven track record of managing both people and processes
  • Adept at wearing multiple hats and serving as the interface between different teams within the company
  • Passionate about personal and professional growth, embracing the highs and lows of a rapidly evolving industry

Benefits & Perks:
Insurance (Medical, Dental, Vision, LTD and a variety of other programs)
401k
Equity
Catered meals (in office)
Variable Base + Commission + 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 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 **

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The Company
San Mateo, CA
18 Employees
Year Founded: 2015

What We Do

Accounts Payable (and Receivable, too) Made Easy!

At Checkbook, we have built a way to send and receive Digital Checks instead of dealing with paper and postage, or expensive online transactions. Digital Checks offer a clear financial and operational advantage for businesses with instant delivery, and online deposit, at a fraction of the cost of other payment options. Just $1 per transaction, regardless of the amount.

No more stuffing and stamping. Simply hit ‘Send’

Send digital checks in seconds with our seamless interface at www.checkbook.io. Simply enter the recipient’s name, email, and the amount -that’s it! The recipient will receive an email of their check that they can instantly deposit, or print if they choose. Have multiple recipients? Upload a CSV file and send mass checks easily. We’re also integrated with Quickbooks! Download the app at the Intuit Marketplace.

Easy Onboarding

The convenience of Checkbook is that recipients do not need a Checkbook account, just an email address. We take care of the rest with instant bank account verification for on-the-spot deposit -or they can print a paper check, if that’s their preference.

Live Check Tracking

No more “I never received a check.” With Checkbook’s integrated accounting dashboard, you can follow every digital check through every point of the process, from delivery and deposit to posting.

The Bottomline

Checkbook’s Digital Check technology is an end-to-end, simplified payments solution that combines both cost-savings and convenience. Get rid of check clutter and go digital today!

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