Chief of Staff

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 are currently 15-20 people based primarily in NYC (just west of SoHo) and looking to grow to ~70 in NYC over the next 3 years. We were founded in 2022 and are backed by top investors including Sequoia.

Our mission is to bring the best of GraphQL and gRPC to the simplicity and ubiquity of REST.

Our business model is to offer a suite of developer platform products to enable every company to offer the kind of developer experience Stripe does around their API.

Our first product is API client libraries as a service – you send us your OpenAPI spec, we let your customers npm install your-company (or equivalent, in several languages).

Our founder, Alex Rattray, created Stripe's API client library codegen system and led a redesign of the Stripe API docs.

The Role:

This role is to be the second brain and right hand of the CEO.

You will act as an inseparable collaborator: driving big initiatives, co-writing strategic documents, taking action items, making sure deadlines are met and progress is being made.

We're seeking an exceptionally organized, reliable, and proactive individual to support our Founder/CEO Alex in myriad different ways.

The focus is on enhancing the CEO's effectiveness by managing and guiding his focus, schedule, priorities, energy, and workflow. Doing this well would have an outsize impact on the trajectory of the company.

Ideal Candidate:

You are:

• Phenomenally organized, reliable, and planful
• Smart, creative, curious, and resourceful
• Skilled, concise writer / communicator
• Able to see around corners and manage chaos with a smile
• Confident enough to guide a strong-willed CEO
• Patient and persistent, with high emotional intelligence
• Adept at developing systems to enhance productivity

Qualifications:

We are looking for someone with 2-4 years of experience in top-tier management consulting or private equity.

We are committed to building a diverse and inclusive workplace. We encourage applications from candidates of all backgrounds, including those from underrepresented groups in tech.

Tech Proficiency:

You are super proficient with at least one productivity tool like Google Sheets, Notion, or Airtable (and probably can rant about why you love that tool).

Key Responsibilities:

• Help CEO set & achieve high-quality goals on daily, weekly, monthly, quarterly, and annual bases. This includes holding the CEO accountable and helping problem-solve when things veer off-track.
• Log in to the CEO's email inbox on a daily basis for triage, responding as the CEO to simple matters and highlighting critical messages for urgent action.
• Develop and implement systems to improve the CEO's time management, focus, and productivity, evolving them in response to constant change
• Manage complex calendaring and scheduling to ensure optimal use of the CEO's time
• Anticipate potential issues and proactively develop solutions well before problems arise
• Collaborate directly with the CEO on key documents (JD’s, strategy memos, investor updates, etc), acting as sounding board for making key decisions
• When the CEO is responsible for tasks prone to procrastination, help keep him focused on them instead of email (up to 1-2h/day)
• Coordinate travel arrangements and itineraries
• Maintain strict confidentiality in all matters

Non-responsibilities:

• Gatekeeping
• Regular travel

Success Metrics:

Within 3-6 months, you should:

• Implement systems that noticeably improve the CEO's punctuality and task completion
• Gain the CEO's trust to manage his email, including drafting responses, archiving low-priority messages, and highlighting critical communications
• Prioritize his tasks effectively on an hourly, daily and weekly basis
• Help ensure he's prioritizing his goals and the company's goals effectively on a monthly, quarterly, and annual basis
• Demonstrate ability to keep the CEO focused on high-priority items and punctual to important meetings
• Be a consistent source of good vibes

Benefits

• We’ll be competitive with early stage companies on cash and provide generous equity grants.
• Great healthcare coverage options.
• Paid commuter benefits.
• Paid team lunch during workdays.
• Flexible PTO.