Head of Strategic Projects, Handshake AI

About Handshake

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

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

• Work hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions

• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others

• Build a massive, fast-growing business with billions in revenue

About the Role

As Head of Strategic Projects, Handshake AI, you will own an AI delivery pod that operates like its own mini business inside Handshake AI. You will lead a multi layered team of managers and SPLs (Strategic Project Leads) and be accountable for throughput, quality, and economics across some of our highest priority, highest pressure initiatives and customers.

You will run your pod like a GM, from Weekly Business Reviews and pod level planning to hands on problem solving when projects are at risk. You will sit at the center of Operations, Product, Growth, and Research, turning evolving data strategies into clear plans, systems, and teams that execute at a very high bar. This role is intensely operational, highly visible, and critical to how Handshake AI scales.

You will be responsible for:

• Owning and leading an AI delivery pod of 8 or more team members (managers and individual contributors) across complex, high stakes data and evaluation projects.

• Running Weekly Business Reviews that track pod performance, drive alignment on metrics, and set clear priorities for SPLs and managers.

• Operating as the GM of your pod, responsible for business outcomes, throughput, quality, and the operational P and L for your portfolio.

• Partnering cross functionally with Product, Growth, and Research to translate evolving data strategies into executable project scopes, systems, and resourcing plans.

• Ensuring high quality delivery of AI training and evaluation datasets, including scoping, workflow design, and system level guardrails for quality and scalability.

• Driving systems level improvements that increase efficiency, quality, and capacity, and that can be adopted across other pods and teams.

• Developing leaders and ICs on your team, through coaching, clear expectations, developmental feedback, and growth opportunities.

• Fostering a high performing culture built on close collaboration, transparency, and a commitment to operational excellence that raises standards across Handshake AI.

What success looks like in the first 6 to 12 months:

• Your pod consistently delivers on or ahead of commitments for our most important AI data and evaluation programs, with clear, referenceable customer and research wins.

• Core operational metrics for your pod improve materially, for example quality, on time delivery, throughput, utilization, and margin.

• SPLs, managers, and peers see you as the clear owner of your business, and your pod becomes a model for how Handshake AI runs high intensity delivery.

• Product, Growth, Research, and Engagement teams proactively pull you into planning and scoping for new initiatives because they trust your judgment, systems thinking, and bar for execution.

You will work closely with:

• Strategic Project Leads (SPLs) and managers to set direction, unblock delivery, build leadership capability, and maintain high standards.

• Operations leadership on headcount planning, pod design, and long term capacity and capability needs.

• Product, Growth, and Research on data strategies, experiment roadmaps, and new offerings that depend on reliable expert data and evaluation.

• Engagement Managers and other GTM leaders to connect pod capacity and performance with customer commitments and revenue goals.

What You Will Bring

Experience:

• 7+ years in operationally intensive or execution heavy environments, such as AI data operations, marketplace operations, technical services, or strategy and operations.

• At least 3+ years of leadership experience managing teams, ideally including multi layered teams with managers and ICs.

• Prior experience in investment banking, private equity or management consulting strongly preferred.

• Proven success driving cross functional outcomes in ambiguous, fast paced settings where stakes and expectations are high.

• Experience operating as an owner of a business line or pod, accountable for both delivery and economics, is a strong plus.

This role works well for people who:

• Want to run a mini business with clear ownership for strategy, team, and results

• Like leading managers and ICs, setting a high bar, and giving direct feedback

• Can zoom out to design systems and zoom in to fix specific issues quickly

• Are comfortable with high visibility, high pressure, and shifting priorities

It is not a good fit if you prefer narrow functional scope, stable routines, or top-down direction. There will be sustained periods of high intensity, including early, late, and weekend work when programs or launches are at critical inflection points. You will often be the person ultimately accountable when something is not working.

People in this role often come from:

• Senior operations or strategy and operations leadership roles at early-stage or high-growth startups

• AI, data, or marketplace companies where they owned a business line, region, or pod with P&L or equivalent accountability

• Consulting, investment banking, or PE backgrounds that transitioned into GM, COO, or head-of-ops style roles

• Founders or early team members who have built and scaled teams, systems, and processes from zero to one and beyond

Prior experience in AI is a plus, but a track record of building and scaling high-performing operations matters more.

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: Internet, commuting, and free lunch/gym in our SF office

🏝 Time Off: Flexible PTO, 15 holidays + 2 flex days

🤝 Connection: Team outings & referral bonuses

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