Chief of Staff

featherlessai· Leadership
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🌍 Remote📍 Remote (US & Canada)📍 San Francisco OfficeFullTime

About this role

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.

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.

Frequently Asked Questions

Is the salary disclosed for the Chief of Staff position at featherlessai?
The salary for this Chief of Staff role at featherlessai is not publicly listed. Click "Apply Now" to learn more about the compensation package on their official careers page.
Is the Chief of Staff job at featherlessai remote?
Yes, this Chief of Staff position at featherlessai is remote, with team members based in Remote (US & Canada), San Francisco Office. You can work from home or anywhere in the supported regions.
Is the Chief of Staff role at featherlessai full-time or part-time?
This is listed as a FullTime position. It is posted as a Chief of Staff role in the Leadership department at featherlessai.
Which team or department does the Chief of Staff at featherlessai belong to?
This Chief of Staff position is part of the Leadership department at featherlessai. See the full job description for more information about the team structure and responsibilities.
How do I apply for the Chief of Staff position at featherlessai?
Click the "Apply Now" button on this page. You will be redirected to featherlessai's official application portal hosted on ashby where you can submit your application directly.
When was the Chief of Staff job at featherlessai posted?
This Chief of Staff position at featherlessai was posted on Aug 8, 2026. Apply as soon as possible — early applications are often reviewed first.
Chief of Staff
featherlessai
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