Chief of Staff, CEO Office & Personal Operations

Job Description

Company Overview

Flosum is a Salesforce-native DevOps and data protection platform trusted by enterprises across technology, financial services, healthcare, energy, and the federal government. We operate with a lean, high-performance culture where every team member has outsized impact. We are financially sustainable, AI-forward, and growing — and we need someone exceptional to help our CEO operate at peak effectiveness across both the business and his personal office.

The Role

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.

Who You Are

• You are sharp, driven, and high-energy with an insatiable appetite for learning and getting things done
• You have a baseline understanding of personal finance, investments, and tax processes — enough to be dangerous and ask the right questions
• You have exposure to or genuine interest in legal processes — you do not need to be a lawyer, but you should be comfortable reading a contract, understanding a filing deadline, and coordinating with attorneys without hand-holding
• You are an exceptional organizer who builds systems, not just to-do lists
• You exercise impeccable judgment and discretion — you will have access to sensitive personal and financial information
• You communicate clearly, directly, and proactively — you do not wait to be asked
• You are comfortable operating independently with minimal supervision and can manage up effectively
• You are tech-savvy and embrace AI tools to maximize your productivity

What You Will Own

Investment & Financial Operations

• 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

Legal Coordination & Light Legal Work

• 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

Personal & Family Operations

• 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

Office & Administrative Operations

• 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

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

What Makes This Role Special

This is a rare opportunity to work directly alongside a CEO and learn how decisions get made at the intersection of business, finance, and personal life. You will not be siloed. You will not be bored. You will build skills across legal, financial, and operational domains that most people do not get exposure to until much later in their careers. If you are ambitious and want a role with real responsibility from day one, we want to hear from you.

Benefits

What We Offer

• Opportunity to shape the digital strategy at a high-growth Salesforce ISV.
• Collaborative, innovative, and mission-driven culture.
• Competitive compensation and benefits.
• Career growth in a fast-scaling company serving global enterprises.

Extras (Benefits & Perks)

• Be part of a global, mission-driven team
• Learn from top leaders in Salesforce DevOps and SaaS sales
• Work on exciting challenges in a rapidly growing industry