Head of Engineering

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

As Head of Engineering at Stainless, you'll lead our engineering organization during a period of significant growth and iteration. Reporting directly to the CEO and serving as a key member of the executive team, you'll shape not just the engineering organization but the company's overall direction.

Your mission

As Head of Engineering, you'll drive three key areas:

Engineering excellence

Lead our technical vision and execution, ensuring we ship great software that delights developers. You'll oversee our core SDK generation product, new product development, and overall infrastructure while setting and maintaining an exceptionally high quality bar.

Team growth

Build and scale a high-performing engineering organization. You'll develop the engineering management team, establish effective processes, and foster a culture of continuous learning and innovation.

Strategic leadership

Partner with the CEO and executive team to shape company direction. You'll engage directly with key customers to understand their needs and help shape our product strategy.

What success looks like

In your first 6 months, you will:

• Develop deep expertise in the API space and our product vision

• Significantly improve our engineering velocity and product reliability

• Partner with our most sophisticated customers to ensure our products scale with their needs

• Mentor high-slope engineers and managers toward rapid career growth

• Source, interview, and close some of the best engineers and managers you’ve ever worked with

Who you are

We're looking for someone who combines technical excellence with strong leadership abilities and strategic thinking. The ideal candidate will be excited about building both great products and great teams, with a passion for developer tools and APIs.

Must have

• Experience leading, managing, and building high-caliber engineering teams

• Strong technical background with ability to credibly supervise full-stack development

• Strong product intuition and a track record of shipping exceptional products

Nice to have

• Direct experience building developer tools or APIs products

• History of successful collaboration with external customers

• Past success exemplifying “build the engine while driving the car” style leadership at high growth startups

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").