Chief of Staff, Office of the CEO
Handshake
Date: 2 weeks ago
City: San Francisco, CA
Contract type: Full time
About Handshake AI
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.
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:
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.
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
- 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.
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