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Chief of Staff

Build operational rhythm to align engineering, sales, and product teams

As Chief of Staff at Featherless AI, you will convert founder instinct into process by owning operational admin like vendor contracts and recruiting-process management. You'll serve as connective tissue between engineering, sales, and product when priorities drift, and help establish leadership meeting cadence and decision follow-through as the company scales past 50 people. You'll also drive special projects that lack clear ownership, shiftin...

Why This Role?

Real ownership over operational areas with direct founder access and impact from day one

Key Responsibilities

  • Manage vendor contracts and renewals, finance/ops logistics, and recruiting-process pipeline tracking
  • Coordinate cross-team alignment between engineering, sales, and product to prevent priority drift
  • Establish operating rhythm including leadership meetings, action-item tracking, and decision follow-through
  • Own special projects that lack clear owners, adapting monthly to highest-priority needs

Requirements

  • 5+ years in high-ownership, fast-moving environments such as startup operations, strategy consulting, or banking
  • Strong judgment under ambiguity
  • Technical fluency to follow engineering syncs and customer calls about inference/model-serving products
  • Ability to ask good questions without needing everything translated

Required Skills

operationsstrategycommunicationproject managementtechnical fluencyoperational managementcross-functional coordinationprocess developmentstrategic thinkingtechnical communication
View Original Description from Ashby Job Boards

Original description from Ashby Job Boards

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.

Salary Context

Similar Operations roles on LokerDollar pay around $183k/yr (range $30k–999.999k/yr, n=180 active listings).

Openness not stated by employer — check the listing

Source
Ashby Job Boards
Job Type
full time
Location
Remote
Category
Seniority
senior
PostedFreshNew & verified
Aug 8, 2026

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Frequently asked questions

Is Chief of Staff at Featherless AI a remote job?
This role is based in Remote. See the listing for remote/onsite details.
What type of employment is Chief of Staff at Featherless AI?
This is a full time position.
How do I apply?
Click the "Apply" button on this page to go to the official application at Featherless AI.

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