Head of Support Engineering

Arcade•San Francisco, CA

2d•$205,000 - $250,000•Remote

About The Position

Arcade is seeking a Head of Support Engineering to build and lead their support function from the ground up. This role is crucial for ensuring customer success as the company's deployments rapidly grow. The ideal candidate will have a strong technical background in infrastructure and authentication, a player-coach mindset, and experience building and scaling support teams for technical B2B products. You will be responsible for establishing L0, L1, and defining escalation paths up to L4, owning L2 support, growing and leading the team, and driving automation. This role reports to the Head of Product and will play a key part in shaping the future product direction based on customer feedback and recurring issues. The goal is to make support a product in itself – fast, technical, and a direct input into product development.

Requirements

Built or led a support team for a technical, B2B product.
Strong technical fluency in infrastructure and auth - OAuth, SSO/SAML, APIs and tool-calling, cloud deployment concepts. You can debug alongside a customer, not just triage.
A player-coach mindset: energized by doing hands-on support with customers and building the process behind it.
Track record designing SLAs, ticket routing, and escalation in a way that balances customer empathy with business reality.
Background in developer, infrastructure, or auth products, and the MCP/AI-agents ecosystem.
AI-pilled: you reach for AI and automation to move fast and keep the customer experience quick.

Nice To Haves

Experience supporting self-hosted enterprise customers.
Hands-on with modern support tooling like Pylon.
Experience with cloud marketplace deployments (AWS/Azure).
San Francisco based (or open to relocating).

Responsibilities

Build the support function from scratch: stand up L0 (docs), L1 (AI & automations), and define the routing, SLAs, and escalation paths up to FDE (L3) and Engineering (L4).
Own L2 support: be the human escalation point for real technical issues - Okta/SSO not working, tools not getting called correctly by the LLM, gateway and user-source configuration, auth edge cases.
Grow and lead the team: scale a world-class support org that customers rave about and sets the technical bar for what a support organization looks like.
Automate aggressively so support does not need to scale with customer count, using an AI-first approach.
Partner with FDE: take over as primary customer contact after first deployment; over time, absorb "standard" onboarding and cluster setup, especially for marketplace (AWS/Azure) deployments.
Close the loop with Product and Engineering: turn recurring tickets and friction into prioritization signal and product fixes.