Head of Support Engineering

Arcade•San Francisco, CA

2d•$205,000 - $250,000•Hybrid

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. This position offers a unique opportunity to shape the future of AI agent support within a fast-growing startup that is building critical infrastructure for the AI revolution. The Head of Support Engineering will report to the Head of Product and will play a key role in driving product development through customer feedback.

Requirements

Built or led a support team for a technical, B2B product.
Strong technical fluency in infrastructure and auth, including OAuth, SSO/SAML, APIs and tool-calling, and cloud deployment concepts.
Ability to debug alongside a customer, not just triage issues.
Player-coach mindset: energized by hands-on support and building processes.
Track record of designing SLAs, ticket routing, and escalations that balance customer empathy with business needs.
Background in developer, infrastructure, or auth products, and familiarity with the MCP/AI-agents ecosystem.
AI-pilled: proactively uses AI and automation to increase speed and efficiency for customer support.

Nice To Haves

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

Responsibilities

Build the support function from scratch, including L0 (docs), L1 (AI & automations), and defining routing, SLAs, and escalation paths up to FDE (L3) and Engineering (L4).
Own L2 support, acting as the human escalation point for technical issues such as Okta/SSO problems, incorrect tool-calling by LLMs, gateway and user-source configuration, and authentication edge cases.
Grow and lead a world-class support organization that customers praise and sets the technical bar for support.
Aggressively automate processes to ensure support does not need to scale linearly with customer count, utilizing an AI-first approach.
Partner with FDE to become the primary customer contact after initial deployment, eventually absorbing standard onboarding and cluster setup, particularly for marketplace (AWS/Azure) deployments.
Close the loop with Product and Engineering by translating recurring tickets and friction points into prioritization signals and product fixes.