Head of Strategic Projects, Handshake AI
Role Overview
This is a senior leadership role where you will manage an AI delivery pod of 8+ team members, acting as a GM to oversee high-stakes data and evaluation projects for AI systems. You will be responsible for operational performance, cross-functional collaboration, and driving systems improvements to ensure quality and scalability. The role involves intense operational oversight, strategic planning, and accountability for business outcomes in a fast-paced, high-pressure environment.
Perks & Benefits
The role is fully remote with benefits including equity, 401(k) match, medical/dental/vision, mental health support, a $500 wellness stipend, and a $2,000 learning stipend. It offers flexible PTO, 15 holidays, and team outings, with an expectation of high-intensity work including early, late, and weekend hours during critical periods. Career growth is supported through leadership development and cross-functional exposure in a high-performance culture.
Full Job Description
About Handshake AI
AI is reshaping how skills are built, how work gets done, and how careers begin. Static credentials and résumé-based hiring no longer reflect how people actually learn or contribute.
Handshake is bridging that gap.
Built on a trusted SaaS platform connecting 22M+ students and alumni, 1,600+ universities, and 1M employers, Handshake is expanding into AI-native work through Handshake AI—partnering with frontier AI labs and leading technology companies to build the human data that powers modern AI systems.
Why join Handshake
Shape how careers work in the AI economy—at global scale
Work with world-class AI labs and Fortune 500 partners
Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir
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.
Similar jobs
Found 6 similar jobs