What are the responsibilities and job description for the Chief of Staff position at Stainless Software, Inc?

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 other great investors.

We are currently 15-20 people based primarily in NYC (just west of SoHo) and looking to grow quickly over the next 3 years.

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, ensuring balls are juggled and deadlines are met.

Where the CEO leads the vision, you drive smooth operations by keeping things organized, on time, and efficient.

Responsibilities

You will :

Run the company operating cadence, including QBRs, annual planning, performance reviews and promotions, employee engagement surveys and resulting improvement initiatives.
Partner on C-level negotiations (employee, customer, or vendor), driving redlining contracts, negotiating financial and business terms, and managing stakeholders.
Become an effective proxy for the CEO, project-managing execution across the company, taking meetings and emails in his stead, and brain-dumping / mind-melding efficiently. You will identify bottlenecks and resolve them yourself.
Shape the company culture and drive high-level people operations (e.g., employee onboarding, engagement, policies, org design, design & conduct key interviews, etc).
Keep a pulse on the team, raising potential issues and opportunities for improvement to CEO and leadership team.
Work closely with CEO to maximize his effectiveness, shaping his priorities, anticipating his needs, developing systems, and guiding difficult do-vs-delegate-vs-drop decisions.
Oversee an administrative assistant (who manages logistics like scheduling) to ensure every minute of the CEO's time is optimally allocated and energizing.
Partner closely on all aspects of investor relations (e.g., board decks, pitch decks, meetings).

Outcomes

Within the first 6-12 months, we'll expect to see that :

The company hums : operations run smoothly, employees are engaged, happy, and productive, and prospects & customers find us to be a consistently reliable partner.

Our internal documents are well-written and organized (e.g., PRDs, hiring plans, company policies, employee onboarding guides, decisions)

Every important meeting (e.g., board meetings, leadership staff meetings, project reviews, all-hands, key customer calls, etc) are superbly well-run, with clear agendas and action items, appropriate use of time, and a great atmosphere.

The CEO is organized, punctual, and reliable. The CEO focuses on the right priorities and does not waste time on the wrong things. The CEO is prepared for every day and every meeting, and every action item coming out is reliably shipped.

Stainless's strategy is clear and strong, with investors and other key stakeholders maintaining buy-in into a compelling vision. All strategic & investor-facing communications are crisp and sound.

You own and delivers special projects with board-level impact every quarter.

Profile

You might be a good fit for this role if :

You're looking to be a founder / leader yourself in the future

You have 3-8 years of experience, comprising :

2-4 years of experience in top-tier business roles (e.g., management consulting, PE, investment banking, big tech APM, or VC)

1-3 years of experience in startups (e.g., in founder, product management, chief of staff, bizops, or similar roles)

You're unfailingly curious, resourceful, and creative

You've managed people, at least on a project basis

You're sharp & kind, with strong IQ and EQ

You're comfortable being assertive and direct

You pride yourself on being exceptionally organized, reliable and productive

You have a strong bias to action and don't hesitate to roll up your sleeves and just it done

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.

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 during workdays.

Flexible PTO plus 2 weeks of companywide vacation a year.

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