Featherless AI
Technology & SoftwareDirect Ashby career site

Chief of Staff

Location
San Francisco, CA (Remote) · On-site
Job type
Full-time
Level
Lead / Staff
Experience
5+ years
Listed
23 days ago

Skills & highlights for this role

  • operations management
  • cross-functional coordination
  • project ownership

Also useful

  • KPI and accountability frameworks
  • recruiting process management

About the Role

We're hiring our first Chief of Staff to unlock our next phase of growth.

Too much context lives in founder's heads. Roles and responsibilities are unclear, key projects lack singular owners / DRI and prioritization is always a challenge. Defining clear KPIs with owners and beating a drum around accountability is a key missing piece that needs an owner. This is the heart of the Chief of Staff role.

This role exists to fix that. You'll convert founder instinct into process - without turning a 40-person company into a bureaucracy. This is not an executive-assistant role, and it's not an "AI adoption lead". You'll have real ownership over operational areas, not just support the CEO's calendar.

We're early enough that this role will be defined significantly by what you're good at. We're looking for someone who's comfortable with that trade.

What You'll Own

  • Operational admin that shouldn't sit with the CEO - vendor contracts and renewals, finance/ops logistics, and recruiting-process management (not sourcing, but the machinery: pipeline tracking, interview loops, offer logistics).
  • Cross-team coordination - you'll be the connective tissue between engineering, sales, and product when priorities drift out of alignment. You notice when teams aren't talking to each other before it becomes a fire.
  • The operating rhythm - as the company grows past 50, you'll help stand up the cadence (leadership meetings, action-item tracking, decision follow-through) that keeps priorities from living only in discord threads and the founder's memory.
  • Special projects - whatever is highest-priority and doesn't have a clear owner yet. This will shift month to month.

What You'll Need

  • 5+ years in a high-ownership, fast-moving environment (startup operations, strategy consulting, banking, or similar) - strong judgment under ambiguity matters more than a specific pedigree.
  • Enough technical fluency to sit in engineering syncs and customer calls and follow what's being discussed. You don't need to have built ML systems, but you should be comfortable enough with how inference/model-serving products work to ask good questions and not need everything translated for you.
  • A track record of turning messy, undefined problems into a plan and driving it to done - with minimal hand-holding.
  • Strong written and verbal communication; you'll be relied on to represent the CEO's intent accurately in rooms the CEO isn't in.
  • Comfort with the fact that this role will change shape as the company scales. Some Chiefs of Staff grow into a functional VP role (Ops, BizOps, etc.); others stay in a generalist seat. We genuinely don't know yet which this will be - it depends on you and on where the company's needs go.

About US

Featherless AI is a 3-year-old, venture-backed AI inference company ($27M raised); we’re building the inference stack for specialized intelligence. We're a team of ~40 people moving fast - and we need someone to help our CEO and leadership team move faster, with less breakage.

Read the original posting

From Featherless AI's careers page, first listed on Rolev.ai on October 17, 2026. Rolev.ai is not the employer.

How Rolev.ai helps with this application

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Common questions

Where is the Chief of Staff job at Featherless AI located?

Yes, this Chief of Staff opening at Featherless AI is listed as San Francisco, CA (Remote) (On-site). Always check Featherless AI's application page for specific state eligibility or relocation policies.

What qualifications are required for Chief of Staff at Featherless AI?

For the Chief of Staff role, Featherless AI highlights 5+ years of relevant experience; experience with operations management, cross-functional coordination, project ownership. Rolev.ai can score your existing resume against these requirements and show any skill gaps before you apply.

How do I apply for the Chief of Staff position at Featherless AI?

This listing links directly to Featherless AI's Ashby application page. You can apply directly on Featherless AI's site, or use Rolev.ai to check your resume fit, generate a zero-hallucination tailored resume and cover letter for this posting, and autofill the Ashby application form in 1 click with the Rolev.ai Chrome extension. You always review the form and press Submit yourself.