Head of Support Engineering

Arcade AI, Inc

$150K — $180K *
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • Built or led a support team for a technical B2B product.
  • Strong technical fluency in infrastructure and authentication tools like OAuth and SSO/SAML.
  • A player-coach mindset, enjoying hands-on support while developing processes.
  • Experience designing SLAs, ticket routing, and escalation processes effectively balancing customer needs and business goals.
  • Background in developer, infrastructure, or authentication products, especially within the MCP/AI-agents ecosystem.
  • Emphasis on AI and automation to enhance the customer support experience.

Responsibilities

  • Build the support function from scratch, developing L0, L1, and L2 support systems.
  • Own L2 support and act as the escalation point for technical issues like Okta/SSO failures and tool-calling errors.
  • Grow and lead the support team, striving for a world-class support organization.
  • Automate processes aggressively to ensure support scales efficiently as customer count increases.
  • Serve as the primary customer contact post-deployment, facilitating a seamless onboarding experience.
  • Transform recurring issues into actionable insights for product enhancements and improvements.

Benefits

  • Opportunity to build a support team from the ground up.
  • Access to critical insights that influence product development.
  • Dynamic role reporting directly to the Head of Product.
  • Chance to work with cutting-edge automation technologies and AI tools.
Full Job Description
The number of deployed Arcade customers is growing rapidly, and after a deployment goes live, someone needs to own everything that happens next. Right now that's ad hoc. We need a leader to build our support function from zero - on a product that looks nothing like typical SaaS. To help a customer succeed, you'll need to understand MCP, OAuth, SSO, tool-calling, and cloud infrastructure. Nobody has been debugging agent authorization at enterprise scale long enough to write the playbook for it. That bar is why Arcade is becoming core infrastructure inside Fortune-100 companies, and it's why this role matters more here than it would anywhere else.

You'll be our first support hire and own the team's growth and processes. For the first several months you'll be doing the L2 support work yourself while you grow the team and build the function. That's how you'll earn the pattern recognition that makes everything you design afterward correct instead of theoretical. This will include not only helping customers, but also improving our docs, configuring agentic support & automations, setting SLAs, and defining escalation paths that let the team scale sub-linearly as customers grow. Do it right and support becomes a product in its own right - fast, technical, and a direct input into what we build next. You'll be reporting to the Head of Product because you'll have some of the strongest signals about what we should build next and we want you sitting right inside the conversation.

What You'll Do
  • 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. Use your experience to 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. An AI-first approach is central to how you'll work.
  • Partner with FDE: take over as primary customer contact after first deployment so FDE can move to the next customer; over time, absorb "standard" onboarding and cluster setup - especially for marketplace (AWS/Azure) deployments to make that experience seamless.
  • Close the loop with Product and Engineering: turn recurring tickets and friction into prioritization signal and product fixes.


Required Skills
  • You've 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.

Bonus Points
  • 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).


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