AI Operations Lead

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.

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.

• 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.

• 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.

• 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
• Mental Health Services
• 401(k) Retirement Plan
• Pre-Tax Commuter Benefit for Parking & Public Transit
• Company-wide Retreats

We are committed to creating a diverse and inclusive workplace. Squint is an equal opportunity employer, welcoming applicants from all backgrounds without regard to race, gender, age, or any other protected characteristic. We encourage you to apply even if you're not quite sure you fit all the requirements for the role!