Head of Customer Support Engineering

Head of Customer Support Engineering

Location: Remote (SF preferred)

Position Type: Full-Time (Permanent)

Work Policy: Remote-first; San Francisco office coming soon

Start Timeline: ASAP

Hiring Target: 1 hire

About

A fast-growing, Y Combinator-backed startup enabling developers to extract AI-ready data from the web

via a single API call. The product has reached multi-millions in ARR and 19K GitHub stars in under a year.

The team previously built Mendable, used by MongoDB, Coinbase, and Snapchat. Now an 8-person,

cash-flow-positive team with upcoming Series A funding.

Why join

• Fast-growing, cashflow positive startup with a beloved product
• Build an AI-powered support function from scratch
• Work directly with founders in a high-impact, fast-paced environment
• Remote-first culture with significant growth opportunities

Compensation

• Base Salary: $200,000 $320,000
• Equity: 0.3% 0.7%
• Visa Sponsorship: Not available
• Tech environment
• Languages: JavaScript
• Database: Postgres
• Tools: Pylon, LLMs, API tooling
• Focus: AI-driven support automation, API reliability, developer-first UX

Role summary: Lead and scale the companys first AI-powered customer support function. This role blends backend engineering and direct technical support (50/50), with heavy use of automation, LLMs, and developer tools.

Responsibilities

• Build & automate: Implement AI-driven support workflows (e.g., using Pylon)
• Technical support: Resolve complex issues related to APIs, scrapers, and data pipelines
• Documentation & process: Create scalable triage systems and self-serve docs
• Customer voice: Synthesize feedback and escalate key themes to product

Must-have qualifications

• 2-5+ years of professional software development experience
• Experience with JavaScript and Postgres
• Proven leadership or ownership in support engineering or developer success
• Experience at a developer-first company or API-focused startup
• Experience using AI support tools (e.g., Pylon), LLM applications, or automating support
• High agency, low ego, and genuine motivation to help users
• Strong written communication skills
• Willingness to do both hands-on customer support and backend infrastructure

Preferred qualifications

• Former founder or early-stage startup engineer (<15-person teams)
• Built side projects or prototypes using LLMs or tools like Cursor
• Active GitHub or portfolio showcasing AI tool experimentation
• Experience scaling support workflows or internal tools