Chief of Staff to the Founder - DiversyFund

About the role

Chief of Staff to the Founder of a multi-line operating company headquartered in San Diego. This is a right-hand-to-the-CEO seat — the person who sits next to the founder daily, runs his week, holds the leadership team accountable, and builds the internal operating systems behind execution.

DiversyFund, Inc. operates as an investment platform, a software business, and an acquisitions engine, backed by a founder-led brand with a large engaged audience. It does not fit a single category, and the right candidate will be energized by that rather than confused by it.

This is not a corporate role. It is not a calendar-management role. It is a builder's seat at a founder-led company in its scaling phase.

Responsibilities

• Run the CEO's week — manage priorities, calendar, decisions, and follow-through
• Coordinate investor and partner meetings — prepare the CEO, debrief after, and track follow-ups to completion
• Hold the leadership team accountable to weekly execution metrics and commitments
• Project-manage execution across multiple active business initiatives
• Build and maintain the internal operating systems, reporting cadences, and accountability structures as the company scales
• Intercept day-to-day operational noise so the CEO can focus on the highest-leverage work — investor relationships, content, and leadership
• Serve as a trusted thought partner to the CEO: push back, tell the truth, and challenge decisions when appropriate

Qualifications

• 3–7 years of professional experience in operations, finance, startup leadership, military, or as a former founder or operator
• Proven ability to build systems and execute in fluid, fast-moving environments without a playbook
• Strong comfort managing up, including holding senior teammates and the founder accountable
• Excellent written and verbal communication
• Data-fluent — able to work with CRM systems, prospect research tools, and reporting dashboards
• Presence and confidence to operate in rooms with strong personalities
• Genuine interest in investing, entrepreneurship, and company-building

Who will thrive in this role

Candidates who have worked somewhere hard — a startup that didn't make it, a finance seat with real stakes, the military, a family business, or their own venture — tend to fit best. Candidates who see themselves as multidimensional operators rather than specialists tend to thrive. Candidates who want equity upside, a real operator seat, and the chance to work next to a founder with three decades of scars and wins will find this seat rare.

Who will not thrive in this role

Candidates from large-tech or large-consulting backgrounds looking for process and hierarchy. Candidates who need a playbook to operate. Candidates looking for remote or hybrid work. Candidates who define "Chief of Staff" as administrative support rather than operational leadership.

Compensation and benefits

• Base salary: $85,000–$110,000 depending on experience
• Performance bonuses tied to execution milestones
• Phantom equity with long-term upside participation
• Direct mentorship from the founder
• High-growth environment with clear paths to expanded responsibility

How to apply

Apply through LinkedIn. Qualified candidates will receive a short questionnaire as the next step. Only candidates who complete the questionnaire will be considered for an interview.