Your impact

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.

Your role

• 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

Your experience

• 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

Traits we are looking for

• 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

Compensation range

• Base cash comp from $225,000-$275,000

• Equity grant vested over 4 years

• Significant performance-based bonuses in both cash and equity

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.

About us

Handshake is building the future of human data for AI.

We partner directly with top AI labs to power large language model (LLM) training and evaluation with high-quality, expert-generated data. As AI models become more sophisticated, the demand for specialized human input continues to grow—and Handshake is uniquely positioned to meet it. We power career platforms at 92% of the top U.S. universities, giving us direct access to verified expert talent across a wide range of domains.

Our AI team is rapidly building a new generation of human data products—from expert annotation platforms to AI interviewers and seamless payout infrastructure—all designed to accelerate research and improve model performance.

We’ve assembled a world-class team from YC, Notion, Scale, Coinbase, Palantir, and more, and we’re working directly with many of the world’s leading AI research labs. 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.