Head of Strategic Projects, Handshake AI

Handshake • San Francisco, CA

4d

About The Position

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.

Requirements

• 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.

Nice To Haves

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

Responsibilities

• 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.

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees