Executive Assistant/Chief of Staff to CEO

Comfy•San Francisco, CA

2d•$130,000 - $180,000•Onsite

About The Position

Comfy is hiring an Executive Assistant/Chief of Staff to support CEO and co-founder Yoland. The role combines executive assistance with broader Chief of Staff responsibilities: managing the CEO’s calendar, inbox, travel, meeting preparation, and follow-through, while independently taking on projects and helping manage his AI agents and tools. The scope is expected to grow as trust is established, and the person hired will help shape how the role works. The position reports directly to Yoland and works closely with the operations and people team. The role requires sound judgment, discretion, strong organization, clear writing, initiative, and comfort with ambiguity and rapidly changing priorities. It is an in-person role in San Francisco. Comfy describes itself as a small, high-intensity team building an AI creation engine for visual professionals. Its product enables users to connect models, processing steps, and outputs in inspectable workflows. The company says it has 4 million users, more than 60,000 community-built nodes, and 150,000+ daily downloads.

Requirements

At least 3 years of experience supporting a founder or C-level executive, ideally at a startup.
Strong judgment about when to act, when to ask, and what is urgent.
Exceptional organization and the ability to maintain personal systems and follow through independently.
Clear, warm writing skills, including the ability to write effectively in another person’s voice.
Discretion in handling investor, board, HR, legal, and finance materials.
Comfort with ambiguity and building processes from scratch.
Fluency with modern tools and AI, with an inclination to automate repetitive work.
A calm, low-ego approach and the ability to stay steady as priorities change quickly.
Based in San Francisco and willing to work in person with the team.

Nice To Haves

Chief of Staff experience or experience owning projects end to end beyond a traditional EA role.
Experience as a SaaS administrator or with IT, access management, or People Ops.
Experience with Google Workspace, Slack, Notion, Superhuman, and Ramp.
Familiarity with the AI or creative-tools space, or experience using Comfy.

Responsibilities

Manage Yoland’s calendar, book and reschedule meetings, protect focus time, resolve conflicts, and coordinate with the team, investors, partners, and candidates.
Prepare briefs for external, board, and investor meetings, including context, objectives, and prior interactions.
Track meeting action items and send follow-ups to ensure commitments are completed.
Triage the CEO’s inbox daily, draft and send email in his voice, and flag urgent or non-urgent matters in Slack.
Maintain a running list of the CEO’s open requests, follow up with the appropriate people, and track items through completion.
Take on follow-up projects, research, and document preparation and run projects independently.
Set up, operate, and check the CEO’s AI agents and automations, and use AI to improve personal productivity.
Arrange flights, hotels, team trips, itineraries, ground transport, and logistics for important office visitors.
Administer company tools, including Slack, Notion, Google Workspace, GitHub, Ramp, and Rippling; handle access requests and support onboarding and offboarding.
Manage NDAs, vendor renewals, and subscriptions, and assist with office and event support as needed.
Help shape the processes and scope of the role as the company and position evolve.