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Chief of Staff / Strategy & Corporate Development Manager
Checkbook
People & HR, Operations
San Mateo, CA, USA
Posted on Aug 20, 2025
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 payments 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 highly driven individual to join as Chief of Staff / Strategy & Corporate Development Manager. This hybrid role offers a unique opportunity to partner directly with the CEO, shape operational strategy, and lead initiatives that fuel company growth. You’ll wear multiple hats: trusted advisor, operator, and dealmaker. Over time, you’ll take on increasing autonomy and influence over the trajectory of the business.
This is the seat for someone who understands fintech, thrives in ambiguity, and wants to help scale a business from the inside out!
Key Responsibilities:
Strategic Initiatives & Corporate Development
- Identify, evaluate, and drive new market opportunities, verticals, and GTM strategies
- Build business cases to support product or geographic expansion
- Source and execute partnerships, integrations, and M&A opportunities - including modeling, diligence, negotiation, and post-deal execution
- Support board and investor communications, including KPI tracking, decks, and scenario planning
- Monitor the FinTech ecosystem - competitors, regulatory changes, and emerging trends - to inform strategy
Operational Leadership & Chief of Staff
- Work closely with the CEO on prioritization, daily execution, and cross-company communication
- Act as a liaison across Product, Engineering, Finance, Marketing, Ops, and GTM teams to ensure alignment
- Establish cadences and systems that keep the company moving efficiently
- Drive accountability and decision-making processes across the leadership team
- Help shape and reinforce company culture as we grow
Requirements for Success:
- At least 4 years of experience as CoS or corporate development, investment banking, VC/PE, or strategy roles in FinTech/startups
- Strong financial modeling, diligence, and negotiation skills
- A proven track record of executing partnerships, deals, or strategic initiatives
- Excellent communication skills - you can distill complex ideas and align stakeholders
- The ability to thrive in fast-moving, ambiguous environments while managing multiple priorities
Bonus Points for having:
- B2B fintech or payments domain experience
- Experience in early-stage, high-growth companies (Seed - Series B)
- Familiarity with BI tools or SQL
- A knack for balancing strategic thinking with rolling up your sleeves
Benefits & Perks:
- Insurance (Medical, Dental, Vision, LTD and a variety of other programs)
- 401k
- Equity
- Unlimited PTO
- Catered meals (in office)
*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 **