Chief of Staff, Office of the CEO

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.

Join us to redefine and reimagine work in the AI economy.

• 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, 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.

We are seeking an exceptional operator to serve as Chief of Staff to our CEO — a role designed for the top 1% of business athletes from the world’s most competitive environments. This is the opportunity to sit at the center of decision-making, operating as a force multiplier for a high-velocity founder/CEO scaling one of the most ambitious technology companies of our time. This role will provide you:

• Direct exposure to company-defining decisions and the highest levels of leadership

• Steep, accelerated learning curve — this is the equivalent of a decade of experience compressed into two years

• Launchpad into executive leadership, venture capital, or founder roles

What You’ll Do:

• Company Strategy — Partner with the CEO and exec team to shape, refine, and operationalize company strategy across all functions.

• Incubation of New Bets — Identify, launch, and operationalize high-potential growth initiatives from concept to scale.

• Operating Rhythm — Own the cadence of business reviews, leadership meetings, and company-wide communication to maintain focus and execution at pace.

• Investor & Board Engagement — Lead preparations and participate in high-stakes investor and board conversations, ensuring clarity, alignment, and strategic impact.

• AI Lab Engagement — Directly represent Handshake AI with the world’s top AI research labs to deepen partnerships and explore new opportunities.

• Drive mission-critical cross-functional projects that span product, go-to-market, and corporate functions.

• Ensure flawless execution on CEO priorities — nothing drops, deadlines are met, and quality remains uncompromising.

• Represent the CEO in select internal and external engagements, delivering consistent quality of message and outcomes.

• Management consulting experience from McKinsey, Bain, or BCG or investment banking from Goldman Sachs, Morgan Stanley, or J.P. Morgan (or equivalency)

• Post-consulting/banking operator experience in business operations, strategy, or chief of staff roles at a top-brand tech company (pre-IPO, unicorn, Forbes Cloud 100 preferred)

• 4–8 years total experience, with at least 2–3 years in consulting/investment banking, followed by 2–4+ years in high-growth tech ops or strategy roles

• Bachelor’s degree; MBA highly preferred

• Skilled in problem analysis, clear executive communication, and prioritizing tasks successfully.

• Relentlessly high output — thrives in fast paced work weeks with sustained intensity

• Able to context-switch across strategy, operations, and execution in minutes

• Holds an uncompromising bar for precision, pace, and quality of work

• Comfort operating in chaotic, founder-driven environments without guardrails

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.