Entrepreneur, CEO Office

About Handshake

In 2014, Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We've grown from $0 to ~$1B run rate and pay ~$15M to 30K+ individuals every week.

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
• Partner hand-in-hand with world-class AI labs, Fortune 500 partners and the world's top educational institutions
• Work together with engineers, scientists, operators, and more from Scale AI, Palantir, Meta, and former YC founders
• Build a massive, fast-growing business with billions in revenue

The Role

Handshake's grown to ~$1B in revenue in record time, and we've hired over 25 ex-founders along the way.

This role is different.

We're looking for an Entrepreneur to join the CEO Office. You'll partner directly with our founders and exec team and tackle the hardest problems at Handshake, building 0-to-1 motions across product, GTM, operations, and more.

That could mean standing up a new internal capability, driving a top priority from idea to execution, building the operating system for an emerging part of the business, or stepping into an urgent company-wide problem and creating order out of ambiguity. You'll be expected to go deep quickly, build strong points of view, align stakeholders, and personally drive intiatives forward.

You'll have high ownership and directly contribute to the success of the company.

Who we're looking for

• A past founder, early employee at a fast-growing startup, or with experience in the venture ecosystem
• Have ambitions of becoming a founder in the future
• Spiky in at least one domain, well-rounded in others
• Killer operator who can build 0-to-1 initiatives in product, GTM, operations, and other areas with the CEO
• Gifted communicator to accelerate the organization by driving alignment internally and represent Handshake to external tech and AI communities
• Move fast, drive outcomes, and leave nothing to chance

Compensation & Benefits

For cash compensation, we set standard ranges for all U.S.-based roles based on function, level, and geographic location, benchmarked against similar stage growth companies. In order to be compliant with local legislation, as well as to provide greater transparency to candidates, we share salary ranges on all job postings regardless of desired hiring location. Final offer amounts are determined by multiple factors, including geographic location as well as candidate experience and expertise, and may vary from the amounts listed above.

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

Equal Employment Opportunity

Handshake is committed to building a diverse and inclusive team. We are an equal opportunity employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity or expression, or any other basis protected by applicable law.

If you require a reasonable accommodation in completing this application, interviewing, completing any pre-employment testing, or otherwise participating in the employee selection process, please direct your inquiries to View email address on click.appcast.io.