Support Lead

Squint AI

$100K — $130K *
Enterprise Technology
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in customer support or technical support role
  • Deep understanding of troubleshooting technical issues
  • Experience in building support tooling and documentation
  • Strong communication skills under pressure

Responsibilities

  • Debug complex customer-reported issues across integrations and APIs
  • Create tooling, runbooks, and escalation paths for support
  • Act as a liaison between customers and engineering/product teams
  • Ensure prompt resolution of customer issues
  • Help define and grow the support organization as the company scales

Benefits

  • Competitive Salary and Equity
  • Comprehensive Medical, Vision, and Dental care
  • Flexible PTO Policy
  • Lunch and Dinner Service
  • Wellness Benefit
  • Maven Family Planning Benefits
  • Partnership with Care.com
  • Mental Health Services
  • 401(k) Retirement Plan
  • Pre-Tax Commuter Benefit for Parking & Public Transit
  • Company-wide Retreats
Full Job Description
About the Role

We're hiring a Support Lead to build Squint's support function.

Sitting within Engineering, this isn't a queue-management role - it's a build role. You'll be the first point of contact for our most complex customer issues, and you'll build the tooling, runbooks, and processes that let support scale as Squint grows.

What You'll Do
  • Solve hard problems: You'll debug customer-reported issues across integrations, APIs, and our AR/AI platform - reading code and logs, not just following a script.
  • Build the function: You'll create the tooling, runbooks, and escalation paths that don't exist yet, using AI tools to help support scale without scaling headcount linearly.
  • Partner tightly with Engineering and Product: You'll be the connective tissue between customer pain and the roadmap, routing feedback with the context and evidence to make it actionable.
  • Own the customer relationship in the moment: When something breaks for a customer, you're calm, clear, and focused on getting them unblocked fast.
  • Grow the function: As Squint scales, you'll help define what a larger support org looks like - process, tooling, and eventually, team.


About you
  • You're calm under pressure and communicate clearly, even when things are on fire.
  • You default to building tools, docs, and process rather than repeating the same manual work over and over.
  • You're genuinely curious about how the product works, and you're comfortable digging in to learn it deeply, even though you're not the one writing the code.
  • You see support as a place to build real influence within Engineering, not a waiting room on the way to something else.


What You'll Bring
  • 5+ years of experience in a customer support, support operations, or technical support role.
  • Comfort learning a technical product deeply enough to troubleshoot issues, reproduce them clearly, and know when and how to escalate.
  • Experience building support tooling, documentation, or process from scratch.
  • Strong written and verbal communication skills, especially under pressure.
Benefits

Based out of our office in San Francisco, we love the energy of in-person collaboration.
  • Competitive Salary and Equity
  • Comprehensive Medical, Vision, and Dental care
  • Flexible PTO Policy
  • Lunch and Dinner Service
  • Wellness Benefit
  • Maven Family Planning Benefits
  • Partnership with Care.com
  • Mental Health Services
  • 401(k) Retirement Plan
  • Pre-Tax Commuter Benefit for Parking & Public Transit
  • Company-wide Retreats


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