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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 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.

Role

You’ll lead product development for the Stainless SDK Studio. You’ll also own creating a new product and line of business around API Docs, partnering with several former Stripe team members who built docs tools there.

Together these web products will be the gateway to Stainless for everyone from startups to established customers like OpenAI, Anthropic, and Cloudflare.

You’ll be one of 2 engineering leaders overseeing Stainless Engineering and will manage 4-12 engineers. This role reports to the CEO and is onsite at our office in Manhattan.

Responsibilities

Day-to-day you will:

  • Think from first principles about creating an outstanding web experience for creating and publishing SDKs.

  • Lead the team in designing and building an API Docs product that sets a new standard in the industry.

  • Personally review every pixel that’s shipped to our customers.

  • Partner with our most sophisticated customers to ensure our Studio scales with their needs.

  • Iterate on our technical architecture to support faster product development and growing scale.

  • Mentor high-slope engineers toward rapid career growth.

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

Profile

You might be a good fit for this role if:

  • You’re a once or future startup founder who enjoys creating new products.

  • You welcome the challenge and commitment required to create a thriving new line of business.

  • You’ve managed a high-performing product engineering team in an early- or growth-stage startup.

  • You’re hands-on: deeply technical, understand in detail what your team is working on, and like to give architecture and product guidance.

  • You’ve personally recruited engineers to join a team you manage.

  • You’re interested in growing your management skills as the team scales over the next 2 years.

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.

What You Should Know About Head of Engineering, Stainless

At Stainless, we're on a mission to revolutionize the world of APIs, and we're searching for a dynamic Head of Engineering to lead our stellar team in New York City. With our clientele ranging from industry giants like OpenAI and Cloudflare to aspiring startups, this role is your chance to shape the future of API development. You’ll dive into creating the Stainless SDK Studio, collaborate closely with a passionate team, and play a pivotal role in building a new product line focused on API documentation. As one of the key engineering leaders, you’ll manage, mentor, and grow a talented group of 4-12 engineers in our vibrant Manhattan office. Your hands-on approach will help us design an outstanding product that excels in user experience, all while ensuring our technical architecture supports our ambitious growth plans. If you're a forward-thinking leader who thrives on innovation and is excited about the challenges of startup life, this is the place for you. Think you can oversee day-to-day engineering operations while also inspiring the next wave of API enhancements? Join us, and let’s redefine the developer experience together!

Frequently Asked Questions (FAQs) for Head of Engineering Role at Stainless
What are the primary responsibilities of the Head of Engineering at Stainless?

The Head of Engineering at Stainless will oversee product development for the Stainless SDK Studio and lead the creation of an API Docs product. You will design and build products that set new industry standards while mentoring and managing a team of engineers, ensuring collaboration with sophisticated customers, and continuously iterating on technical architecture to support rapid growth.

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What qualifications are needed for the Head of Engineering position at Stainless?

To thrive as the Head of Engineering at Stainless, you should have experience managing high-performing product engineering teams in early or growth-stage startups. A deep technical understanding of API development and a hands-on approach to architecture and product guidance are essential. You should also possess a strong background in recruiting and mentoring engineers.

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How does the Head of Engineering contribute to product innovation at Stainless?

As the Head of Engineering, you will play a crucial role in driving product innovation at Stainless. Your responsibility includes leading the design of new products like the Stainless SDK Studio and API Docs, while ensuring that the engineering team focuses on creating outstanding user experiences. Your guidance and expertise in API development will shape the direction of our offerings.

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What kind of team dynamics can the Head of Engineering expect at Stainless?

The Head of Engineering can expect a collaborative and innovative team dynamic at Stainless. You’ll work closely with a group of passionate engineers and have the opportunity to foster an environment that encourages creativity and growth. Your leadership will help cultivate a culture where team members are motivated to excel and contribute to the company's mission.

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What benefits does the Head of Engineering receive at Stainless?

At Stainless, the Head of Engineering can expect competitive compensation alongside generous equity grants. Additional benefits include excellent healthcare coverage, paid commuter benefits, team lunches on workdays, and flexible paid time off. We prioritize the well-being of our team members while ensuring they have the resources to succeed.

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Common Interview Questions for Head of Engineering
Can you describe your experience managing engineering teams in a startup environment?

In responding to this question, focus on specific examples from your past roles. Highlight your leadership style, how you fostered teamwork and innovation, and particular challenges you faced in a startup setting. Be ready to discuss metrics or outcomes that resulted from your team's efforts.

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What is your approach to API design and development?

A successful answer should outline your philosophy on API design, such as adhering to best practices, focusing on developer experience, and ensuring scalability. Share any frameworks or tools you commonly use, along with examples of successful APIs you've developed and the impact they had.

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How do you ensure that your engineering team remains motivated and productive?

Explain your strategies for maintaining team motivation, such as setting clear goals, providing regular feedback, and creating opportunities for professional development. Discuss how you've built a positive culture that encourages creativity and collaboration among team members.

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What methodologies have you used in managing engineering projects?

Mention any specific project management methodologies like Agile, Scrum, or Kanban that you’ve successfully implemented. Discuss how these methodologies have improved project delivery and team accountability, and provide examples that illustrate their effectiveness.

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How do you handle conflicts within your engineering team?

In your response, highlight your conflict resolution techniques. Discuss how you prioritize open communication, actively listen to your team members, and mediate disputes while maintaining a positive team environment. Sharing a specific instance can enhance the response.

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What experience do you have with API documentation tools?

Talk about your familiarity with various API documentation frameworks, emphasizing how you’ve used these tools to improve clarity and accessibility. Discuss specific experiences where you’ve contributed to or led the creation of API docs that enhanced user understanding.

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Can you share a time you had to pivot an engineering project?

Provide a compelling narrative detailing the situation, the factors leading to the decision to pivot, and the ultimate results of that pivot. Emphasize your ability to remain flexible and adapt to changing requirements while keeping your team aligned.

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How do you stay current with developments in technology and engineering best practices?

Your answer should reflect your commitment to continuous learning. Mention relevant publications, industry conferences, or communities you engage with. Discuss how you encourage your team to also pursue knowledge and innovation.

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What role do you believe documentation plays in API development?

Articulate your belief that documentation is fundamental for a successful API. Discuss its role in reducing the learning curve for developers, ensuring effective usage, and fostering integration. Share instances where good documentation made a significant difference in user adoption.

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What strategies would you implement to ensure alignment with our business goals?

Discuss how you would engage with senior leadership to understand business objectives and translate these into engineering initiatives. Emphasize the importance of regular check-ins and feedback loops between engineering and other departments to ensure alignment and responsiveness to business needs.

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Full-time, on-site
DATE POSTED
December 3, 2024

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