Chief of Staff
Featherless AI · San Francisco
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.