AI Operations Lead

Squint AI

$120K — $160K *
Enterprise Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 2-5+ years in business operations, strategy, technical program management, or applied AI with hands-on building experience.
  • Proven experience shipping AI-powered tools, prototypes, or automations (portfolio/examples preferred).
  • Familiarity with modern AI coding and agent tooling (e.g., Cursor, Claude Code).
  • Comfortable with light coding or low-code/agent tooling.
  • Strong written and verbal communication skills for cross-functional collaboration.

Responsibilities

  • Design, build, and ship AI agents and automations for internal teams.
  • Establish evaluation frameworks to monitor AI workflow efficiency.
  • Identify and prioritize workflows for automation vs. human execution based on evidence.
  • Facilitate cross-functional partnerships to enhance AI integration and utility.
  • Drive user adoption and ensure trust in AI tools across teams.

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 for AI Ops, a new role on our Strategy team focused on operationalizing AI inside Squint itself.

Squint builds an AI-native platform for our customers - this role makes sure we're using AI just as effectively to run our own company. You'll build and ship internal AI agents and workflows, own how we evaluate whether they're actually working, and partner across the company to find where AI can replace busywork with real leverage.

What You'll Do

Build real things: You'll design, build, and ship AI agents and automations that make internal teams (Support, Ops, GTM, and beyond) faster and more effective.

Own quality, not just adoption: You'll build the evaluation frameworks and monitoring that tell us whether an AI workflow is actually working - not just whether it's live.

Find the leverage: You'll partner cross-functionally to identify which workflows are worth automating, and which should stay human, and make that call based on evidence.

Drive adoption: Shipping a good agent is half the job - you'll also make sure teams actually adopt and trust it.

About you
  • You've actually built and shipped AI tools or agents - this isn't a roadmap-ownership role.
  • You're fluent with modern AI coding and agent tooling (Cursor, Claude Code, or similar).
  • You can talk to both a technical engineer and a non-technical operator about the same problem.
  • You care as much about whether something works as whether it shipped.


What You'll Bring
  • 2-5+ years of experience in business operations, strategy, technical program management, or applied AI, with hands-on building experience.
  • Demonstrated experience shipping AI-powered tools, prototypes, or automations (a portfolio or examples are a strong plus).
  • Comfort with light coding or low-code/agent tooling.
  • Strong written and verbal communication skills for cross-functional influence.
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


A Final Note

Ready to redefine the future? Join us at Squint and be a part of something revolutionary.

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