Hands-on Head of Customer Support Engineering

Head of Customer Support Engineering
Compensation: $200K$320K + 0.3%0.7% Equity
Location: Remote (SF preferred) | Full-time | No Visa Sponsorship

Who Are We?

Were a high-velocity dev tools startup that helps developers extract and structure clean, LLM-ready data from the web. In under a year, we've gone from 0 to multi-millions in ARR, gained 19K+ GitHub stars, and have a user base that spans indie hackers to engineers at major tech companies. Our product is growing fast. Our inbound support queue is growing faster.

That's where you come in.

Were hiring a Head of Customer Support Engineering a rare blend of true engineer, startup operator, and user-obsessed problem solver. You'll be our first dedicated support hire. Its a hands-on role: you'll be shipping code, building AI-first systems, and responding directly to our users across email, Discord, and Twitter. This is a core IC position with leadership potential designed for someone who wants to own a function and build it their way.

What's In It For You?

• Build from Zero: Architect and implement our support function from scratch tooling, documentation, AI workflows, and more.

• Full Ownership: You'll work directly with the founders and own support top-to-bottom.

• No Bureaucracy: Just you, a fast product loop, and a culture of high trust and autonomy.

• Real Technical Work: This isn't a CX or success role dressed up as engineering. You'll be deep in the stack solving real problems.

• Growth Trajectory: You'll shape the company's customer experience now and have the option to lead a team later.

What You'll Do

• Build and own support automation infrastructure (e.g., Pylon, LLM agents, custom triage tooling).

• Solve user-facing bugs and unblock customers directly in the codebase (JS/Node, Postgres).

• Maintain and scale self-serve docs, runbooks, and customer-facing resources.

• Analyze trends and user feedback to drive product improvements and issue prevention.

• Triage and respond to support requests across Discord, Twitter, and email.

• Be the voice of the customer and a partner to engineering, growth, and product.

What Were Looking For

This is not a traditional support role. Were looking for someone with:

• 25+ years of experience as a software engineer (bonus if full-stack with JS and Postgres).

• Experience using LLMs daily for dev workflows, support tools, or automation. You build with AI, not just read about it.

• A track record of side projects, GitHub contributions, or founder-like initiatives.

• A deep desire to help customers succeed even if that means rolling up your sleeves at 2am to debug a gnarly issue.

• High agency, low ego, and strong care. You get stuff done, don't need babysitting, and take pride in doing it well.

Bonus Points For

• Founder or early team experience at a startup (<15 people).

• Supporting or building developer-facing tools or APIs.

• Building AI-driven internal tools or support automation workflows.

• Deep GitHub activity and side projects you're proud of.

What You're Not

• Someone who wants to try customer support but is really aiming for a product or platform engineering role.

• A customer success or support specialist who hasn't written production code.

• Someone who doesn't use LLMs/tools like ChatGPT, Cursor, or Copilot regularly.

Important Notes:

• This is an IC role, despite the title. You'll be doing the work building, shipping, fixing not managing a team out of the gate.

• The company is currently remote with plans for a San Francisco office. Preference is given to candidates in or open to relocating to SF.

• Visa sponsorship is not available at this time.

If you're a builder who loves talking to users, automating the boring stuff, and solving real-world problems fast this is your role.