Checkbook Intern: Operations, Legal & People Ops

Hey there, future intern 👋
This is not a traditional internship.

This role is designed for someone who wants early, meaningful exposure to executive decision-making in a growing fintech. You will work directly with the Co-CEO & General Counsel, with regular interaction with the Chief Operating Officer and People Operations Manager. You’ll see how senior leaders evaluate risk, manage priorities, and keep the company operating day to day.

You’ll be entrusted with real work that matters—reviewing and organizing legal documents, supporting compliance and operational workflows, coordinating leadership schedules, and helping ensure nothing critical slips through the cracks. We’ll teach you how to do the work properly, explain the context behind it, and expect you to apply what you learn quickly.

This role is best suited for someone who wants to build judgment, credibility, and executive-level operating experience early.

What You’ll Do

Legal / Executive Coordination

• Monitor shared Legal and Compliance inboxes; identify what requires immediate attention versus background noise
• Organize and review legal documents (yes, real ones—and we’ll teach you how to approach them)
• Track requests, deadlines, and follow-ups to ensure leadership priorities are executed
• Manage calendars and coordinate meetings for executive leadership using tools like Calendly and Doodle
• Act as a point of coordination on scheduling and logistics for senior leadership

People Ops

• Support employee onboarding, internal documentation, and People Ops initiatives
• Assist with employee experience and culture-related projects
• Help maintain People Ops systems, records, and operational discipline

Operations Support

• Support the COO on operational projects, including customer onboarding and risk-related work
• Help document, improve, and maintain operational processes across the business
• Assist with research, process improvements, and operational cleanups
• Bonus: support light data analysis or reporting to inform operational decisions

• You want responsibility and proximity to decision-makers, not busywork
• You’re organized, detail-oriented, and comfortable handling sensitive information
• You manage time and priorities well and don’t need constant oversight
• You’re intellectually curious and want to understand why decisions are made, not just how
• You communicate clearly and professionally, especially in writing
• You bring some foundational exposure to legal, operations, HR, or startup environments

• Direct exposure to executive leadership and how a fintech is actually run
• Practical experience working with legal documents, compliance workflows, and operational systems
• A front-row seat to how senior leaders evaluate risk, tradeoffs, and priorities
• Skills and judgment that translate well to law, consulting, finance, operations, or startup careers

Info, Benefits & Perks:

• Location: US remote or in office in San Mateo, CA if local
• Hours: 15-20 hours per week during the school year, with the goal of moving to full time during summer break
• Compensation: Hourly pay, based on experience
• Benefits: This role is not benefits-eligible while part-time. If converted to full-time, the position is eligible for medical, dental, vision, long-term disability, and other Company-sponsored benefit programs, as well as participation in the Company’s 401(k) plan.
• Other Perks: Catered meals when working in the San Mateo 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.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 **