About the role

Role Overview

Chief of Staff & Director of Special Projects (Chief of Staff to the CEO) at Swooped is a high-leverage, high-trust role serving as the CEO’s closest thought partner and force multiplier. The position blends communication with operator instincts: you’ll write with precision, handle sensitive stakeholder situations discreetly, and turn ambiguous ideas into shipped outcomes.

Key Responsibilities

Office of the CEO (Management)

Run the CEO’s office by coordinating focus and priorities aligned to organizational needs
Support strategic external communications: triage incoming messages, draft responses, and ensure timely follow-up
Field and triage meeting requests on the CEO’s behalf, taking meetings independently where appropriate and preparing briefings for high-stakes engagements
Act as a proxy for the CEO in decision-making and follow-ups, owning next steps
Partner with the CEO’s EA on scheduling, travel, expenses, and inbox management; optimize travel time for relationship-building with external partners, program teams, and funders

Communications & Marketing

Own executive communications for the CEO, including thought leadership via Substack, LinkedIn, and other channels, plus the organization’s podcast
Lead CEO/executive media relations in coordination with the Communications lead (respond to inbound and proactively engage journalists)
Support development of presentations and workshop facilitation materials so the CEO shows up polished and on-message

Location / Work Setup

Full-time, exempt role
Remote in the United States on a flexible schedule; preference for candidates able to work PST hours
Up to 40% travel within the U.S.

Compensation & Benefits

Salary range: $150,000–$175,000 (depending on experience)
Comprehensive benefits: health/dental/vision, life insurance, short- and long-term disability, flexible work hours/location, flexible PTO, paid parental leave, home office + professional development stipend, and 401(k) match of 4% vested immediately

Start Date

Start as soon as possible after offer (some flexibility)

About Swooped

Swooped is a 501(c)(3) non-profit focused on creating equitable educational experiences that build AI literacy. The organization teaches students—especially those disproportionately impacted by AI and automation—the concepts and skills needed to succeed as future workers, creators, consumers, and citizens.

Tags