Freelance Ai Operator Jobs (NOW HIRING)

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

Why join Handshake now:

• Shape how every career evolves in the AI economy, at global scale, with impact your friends, family and peers can see and feel

• Work hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions

• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others

• Build a massive, fast-growing business with billions in revenue

Handshake AI matches domain experts with leading AI companies to train frontier models. We're hiring a Product Manager for our Pay & Safety squad to own how we pay our fellows and how we keep our marketplace trustworthy.

Tens of thousands of fellows rely on HAI to pay them accurately and on time every week. The Pay team has built the foundation, including admin-managed payroll, referrals at scale, and incentives tied to pipeline stage, but the surface area is growing faster than the team can keep up with. You'll own the roadmap for what's next, including withholding tax compliance, off-platform time tracking, in-product adjustments, international payouts, and securing payroll against fraud.

You'll also lead the team's expansion into Trust & Safety. Fraud detection at HAI today is largely manual. Operators run queries by hand and react after customers flag bad actors. The gap costs us millions of dollars per month between payouts to fraudsters, false-positive churn, and lost revenue. Your job is to move detection from reactive to proactive: ingest the relevant risk and trust signals, build the system that acts on them, and give operators tooling that replaces the manual work they do today.

You'll be part of a cross-functional squad with engineers and designers, working closely with Operations, Finance, T&S, and Growth.

• Pay platform. The roadmap for accurate, on-time pay. Active areas include payroll automation, withholding tax support, in-product adjustments and incentives v2, off-platform time tracking, and HAI international payouts.

• Trust & Safety platform. Build out HAI's proactive fraud detection system. This covers ingesting 50+ risk and 10+ trust signals, launching a Fraud Center, guided PII verification flows by risk level, automated actioning, and IP/VPN/persona improvements.

• Operator tooling for Pay & Safety. Our team currently fields pay disputes and runs fraud queries manually. Your job is to build the dashboards, status systems, and self-serve flows that reduce that work.

• Goals and metrics. Define and track targets including: % of payouts executed without manual adjustment, weekly withholding tax exposure, monthly referrals, customer-flagged fraud rate, fraud detection recall and precision, median time to verify, and % of verifications automated.

• Cross-functional partnership. Work with Finance on payroll and tax, with T&S on signals and policy, with Growth on referrals GTM, and with sibling squads where workflows overlap.

• 3+ years as a product manager shipping production code with engineering teams.

• Experience with payments, payroll, billing, or another money-movement product where bugs have real financial consequences.

• A track record building tools for internal users like finance, operations, T&S, or similar.

• Comfortable reasoning across systems with many inputs and dependencies (KYC, tax forms, IP data, device fingerprints, project allocations, audit logs).

• Data-informed and action-oriented. You use precision/recall, payout error rates, and on-call volume to prioritize, and you move quickly once the signal is clear.

• Background in trust & safety, fraud detection, identity verification, or risk operations

• Experience at a marketplace, gig platform, or human-data company

• Exposure to AI/ML data pipelines or annotation workflows

Handshake delivers benefits that help you feel supported and thrive at work and in life.

The below benefits are for full-time US employees.

🎯 Ownership: Equity in a fast-growing company

💰 Financial Wellness: 401(k) match, competitive compensation, financial coaching

🍼 Family Support: Paid parental leave, fertility benefits, parental coaching

💝 Wellbeing: Medical, dental, and vision, mental health support, $500 wellness stipend

📚 Growth: $2,000 learning stipend, ongoing development

💻 Remote & Office: Internet, commuting, and free lunch/gym in our SF office

🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days

🤝 Connection: Team outings & referral bonuses

Explore our mission, values, and comprehensive US benefits at joinhandshake.com/careers.

Compensation Range: $145K - $180K