Head of Strategic Projects, Handshake AI

About Handshake AI

Handshake is building the career network for the AI economy. Our three-sided marketplace connects 18 million students and alumni, 1,500+ academic institutions across the U.S. and Europe, and 1 million employers to power how the next generation explores careers, builds skills, and gets hired.

Handshake AI is a human data labeling business that leverages the scale of the largest early career network. We work directly with the world’s leading AI research labs to build a new generation of human data products. From PhDs in physics to undergrads fluent in LLMs, Handshake AI is the trusted partner for domain-specific data and evaluation at scale.

This is a unique opportunity to join a fast-growing team shaping the future of AI through better data, better tools, and better systems—for experts, by experts.

Now’s a great time to join Handshake. Here’s why:

• Leading the AI Career Revolution: Be part of the team redefining work in the AI economy for millions worldwide.

• Proven Market Demand: Deep employer partnerships across Fortune 500s and the world’s leading AI research labs.

• World-Class Team: Leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, just to name a few.

• Capitalized & Scaling: $3.5B valuation from top investors including Kleiner Perkins, True Ventures, Notable Capital, and more.

About the Role

Handshake is expanding into AI research and development, building a world-class network of expert Fellows - PhDs, researchers, and subject matter specialists - who contribute to cutting-edge AI through specialized research, model evaluation, and domain-specific applications. We’re looking for an entrepreneurial, systems-minded operator to serve as a Head of Strategic Projects - owning a delivery pod within Handshake AI. You’ll lead a 8+ person team, including managers and individual contributors, to drive execution across some of our highest-priority, high-velocity AI data initiatives.

Each pod operates like its own mini-business within Handshake AI - you’ll be responsible for aligning cross-functionally with Product, Growth, and Research, running Weekly Business Reviews, and scaling operational excellence in a fast-changing, high-stakes environment.

This is a high-impact, multi-dimensional leadership role where you’ll combine strategic thinking with hands-on operational rigor to unlock quality, throughput, and innovation at scale.

This position is based in San Francisco or New York and this team is in the office five days a week.

• Own and lead an AI Delivery Pod consisting of 8+ team members (managers + individual contributors) across complex, high-stakes data projects

• Run Weekly Business Reviews tracking pod-level performance, driving alignment on metrics, and setting clear priorities

• Operate as a GM of your pod, responsible for business outcomes, throughput, quality, and operational P&L

• Partner cross-functionally with Product, Growth, and Research teams to execute against evolving data strategies

• Ensure high quality delivery of AI training datasets by scoping projects, designing systems,

• Drive systems-level improvements to increase pod efficiency, quality, and scalability

• Experiment, iterate, and problem-solve in ambiguity, bringing structure and clarity to complex operational challenges

• Develop the team through active coaching, building upon strengths and providing developmental feedback and opportunities to advance their professional careers

• Foster a high-performing culture built on close collaboration, transparency, and a commitment to operational excellence that elevates team standards

Desired Capabilities

• 7+ years of professional experience in operationally intensive or execution-heavy environments

• At least 2+ years of leadership experience managing teams; ideally including managing multi-layered teams (managers + ICs)

• Proven success driving cross-functional outcomes in ambiguous, fast-paced settings

• Metrics-driven operator who can scale systems, improve throughput, and maintain high-quality standards at speed

• Ability to zoom in and out - comfortable with hands-on operational detail as well as strategic, systems-level thinking

• Strong cross-functional fluency - you’ve worked closely with product, engineering, or growth teams to deliver on shared business goals

• Entrepreneurial mindset, with experience either as a founder, early-stage startup operator, or someone who has taken ownership of end-to-end outcomes in a high-growth environment

• Technical fluency or a STEM background is a strong plus

Extra Credit

• Excellent written and verbal communication skills

• Strong sense of ownership and pride in their work

• Technical background with fluency in programming languages and/or SQL

• High degree of agency - ideal candidate can thrive in ambiguity

• Passionate about / interested in AI (super user of LLMs, up-to-date on latest AI trends)

• Critical thinker / first principles approach to solving problems

• Data driven decision maker

• Thoughtful about making decisions - doesn’t jump to conclusions without considering all potential variables/curve balls

• The drive and competitiveness to win in a rapidly growing market

Potential Backgrounds

We’ve seen success with candidates who have:

• Managed high-velocity data operations at AI companies or marketplace businesses

• Founded a company that achieved meaningful traction, network growth, or early revenue scale

• Worked in early-stage startups in operational leadership roles with cross-functional business responsibilities

• Spent time in consulting or investment banking, then transitioned into ops/product leadership at startups

Benefits & Perks

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: Stipends for home office setup, internet, commuting, and free lunch/gym in our SF office

🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days, winter #ShakeBreak where our whole office closes for a week!

🤝 Connection: Team outings & referral bonuses

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