Chief of Staff, CEO Office & Personal Operations

Flosum•San Ramon, CA

About The Position

The ideal candidate will reside in San Ramon California, or in the Bay Area. This is not a typical executive assistant position. You will serve as the operational right hand to Flosum's CEO, managing a blend of professional and personal operations that require intelligence, discretion, financial literacy, and legal awareness. Think of yourself as a one-person chief of staff for the CEO's entire life — investments, legal coordination, family logistics, office administration, and everything in between. You will be the single point of accountability for ensuring that nothing falls through the cracks across a complex, fast-moving set of responsibilities. If you thrive on variety, can context-switch between a tax filing and a college application in the same hour, and want a role where you learn how a CEO actually operates day to day — this is it.

Requirements

2-5 years of experience in executive support, operations, legal administration, financial coordination, or a similar role combining multiple disciplines
Bachelor's degree required; coursework or certification in business, finance, pre-law, paralegal studies, or a related field is a strong plus
Demonstrated ability to manage complex, multi-track workstreams with competing deadlines
Experience coordinating with external professionals (attorneys, accountants, financial advisors)
Familiarity with personal tax filings, investment documentation, and basic legal agreements
Proficiency with productivity and AI tools — Google Workspace, Microsoft Office, and a willingness to adopt new technology aggressively
Must be trustworthy, discreet, and comfortable handling confidential information

Responsibilities

Coordinate with financial advisors, accountants, and investment managers on behalf of the CEO
Track and organize personal investment portfolios, statements, and financial correspondence
Manage tax preparation workflows — gather documents, coordinate with CPAs, track deadlines, and ensure timely filings for both personal and business-related obligations
Process, organize, and resolve incoming financial paperwork, invoices, and office mail efficiently
Maintain a clear system for accounts payable, reimbursements, and recurring financial commitments
Serve as the primary liaison with attorneys, legal agencies, and regulatory bodies for personal and light business legal matters
Review, organize, and track contracts, agreements, and legal correspondence
Manage timelines for legal filings, renewals, and compliance deadlines
Conduct basic legal research and prepare summaries to support decision-making
Coordinate with local government agencies and offices on permits, filings, and documentation
Manage logistics for family-related matters including college applications, enrollment, academic deadlines, and school communications
Coordinate medical appointments, insurance paperwork, and health-related administration for the CEO's family
Handle personal scheduling, travel, and logistics that intersect with professional commitments
Serve as the go-to problem solver for personal administrative needs, ensuring fast resolution
Own the CEO's incoming mail — physical and digital — with a system for triage, action, and follow-up
Maintain organized records and filing systems across financial, legal, and personal domains
Identify and implement tools and processes that increase efficiency across all areas of responsibility
Proactively flag issues, deadlines, and risks before they become problems