Executive Assistant

About Stainless

Stainless is a fast-growing tech startup building the future of APIs. Our customers include industry leaders like OpenAI, Anthropic, and Cloudflare.

We have raised over $35 million from a16z, Sequoia, and founders/C-levels from Stripe, Datadog, Segment, Linear, and more.

We are headquartered in NYC, just west of SoHo, and expect to grow from ~20 to ~40 people in 2025.

Role Overview

We’re hiring an Executive Assistant to support our Founder/CEO, Alex, and help keep our growing company running smoothly. This role combines aspects of a traditional EA, a Chief of Staff, and execution partner — think EA++.

Your work will be focused on helping Alex manage his focus, schedule, priorities, and energy — basically, making sure he spends his time on the things that matter most. Done well, this role has the potential for outsized impact not only on Alex’s effectiveness, but on Stainless’s trajectory.

If you’re highly organized, enjoy supporting others, and thrive in the mix of structure and chaos that comes with working alongside a fast-moving founder, we’d love to hear from you.

About Alex

Alex, our CEO, is driven, ambitious, a little quirky, and thrives on energy and ideas. He benefits from structure and systems to help him do his best work. Your role is to be his partner in building that structure: the person who helps him stay on track, prepared, and focused on the highest-leverage work.

What You Do

On a day-to-day basis, you will:

• Help Alex set and follow through on goals — daily, weekly, quarterly, and annual.
• Handle all of the behind-the-scenes details that keep Alex energized and focused on what matters most. You’ll schedule workouts, ensure he gets proper meals, manage personal appointments, and all of life’s random logistics.
• Manage his inbox, calendar, and TODO list, making sure urgent things surface and distractions don’t.
• Design and evolve systems that make him more effective and the company more resilient.
• Partner with Alex on all written communications, helping craft, edit, and refine his ideas into clear, compelling content.
• Be a steady, positive presence in the middle of the inevitable startup chaos.

Tl;dr, the work is varied: some days it’s writing, other days it’s problem-solving, coaching, or quietly making sure nothing slips through the cracks.

Who You Are

Your background could be in executive support, teaching, operations, or something else entirely. What matters most is that you’re skilled at helping ambitious, distracted people do their best work.

• Organization and reliability – You bring order to chaos, and others trust you to follow through.
• Strong communication – You write clearly, concisely, and can shift tone to match context.
• Emotional intelligence – You balance empathy and firmness, supporting Alex while keeping him accountable.
• Judgment – You know when to push, when to step back, and what truly matters in a sea of competing demands.
• Proactivity – You spot problems before they surface and solve them with minimal direction, but can balance this against when it makes sense to check in.
• Patience and persistence – You don’t get rattled easily, and you know progress comes from consistency.
• Background - Have experience in executive support, operations, teaching, or similar fast-paced, detail-heavy environments.
• Acts of service energize you - you find deep satisfaction in enabling others' success through thoughtful support.

What Makes This Role Unique

This isn’t your typical EA role. If these aspects excite you, we’d love to talk:

• You'll become a systems architect - Alex thinks in frameworks and processes. You'll build detailed systems that actually work, then iterate on them constantly. If you love creating order from complexity and get satisfaction from perfecting the small details that drive big outcomes, this role offers that in spades.
• You'll match founder intensity - When big decisions are being made or deadlines loom, expect to be all-in alongside Alex. That might mean weekend strategy sessions, late-night prep for important meetings, or rapid pivots when priorities shift. If you thrive on being essential to the most critical moments, this energy will be rewarding rather than draining.
• You'll work with someone who has strong opinions - Alex has perspectives on everything from product roadmap to meeting structures to email formatting. You'll need to be comfortable pushing back thoughtfully when needed, while also appreciating that his attention to detail often leads to better outcomes. If you enjoy intellectual sparring and can hold your own in debates about process and priorities, you'll be a great thought partner.
• You'll adapt constantly - As we grow, what worked last quarter might not work this quarter. You'll be redesigning systems, rethinking approaches, and staying curious about better ways to do things.

This is a full-time role, in-person in New York. Most of your time will be in the office, with some flexibility to step out during the day. This role requires evening and weekend work.

Benefits

• We offer competitive salary and generous equity grants.
• Great healthcare coverage options (e.g., fully covered platinum plans).
• Paid commuter benefits & similar.
• Paid team lunch/meals during workdays.
• Flexible PTO plus 3 weeks of company-wide vacation a year (2 weeks in December, 1 week at the end of the summer).
• Flexible WFH and 1 month fully remote per year ("remote February").