Director of Marketing, Enterprise AI

About Handshake

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 ~$60M to over 30K individuals every month.

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 Palantir, Meta, Scale AI, and former YC founders
Build a massive, fast-growing business with billions in revenue

About Handshake AI

Human data is the core infrastructure to AI advancement. Frontier AI labs currently improve model capabilities with various data-intensive post-training techniques. We believe that data spend for AI training will increase by 3-5x in the next few years and continue for much longer as models take on new domains. Handshake AI supports all of the frontier AI labs, working on their most complex data at the largest scale.

The Role

Handshake built the eval and human-data infrastructure that frontier AI labs rely on to make their models and agents better. We deliver capabilities from RL environments to expert-in-the-loop eval construction, and post-training systems. Now, we are pointing that same infrastructure at the enterprise: helping Fortune 500 companies in banking, insurance, retail, and legal build the eval and improvement loops their AI agents need to work safely and well in production.

This is the founding marketing role for this new line of business — and at its core, a product marketing role: positioning, technical narrative, and sales partnership come first. You will be working with company leadership directly and you'll have the full weight of Handshake's marketing org, brand, and infrastructure behind you, with the autonomy to build the Enterprise AI motion from the ground up. You'll lead and build the positioning, technical content, a lighthouse-account ABM motion, and sales enablement all while working directly with the Enterprise AI founding team. You'll have high visibility and close proximity to CEO Garrett. It's a high-ownership opportunity inside a larger $250M+ company build-out. If this line of business becomes what we expect it to, this founding role grows into a team you build and lead.

Own positioning and messaging end-to-end — define the ICP, build the competitive narrative, and stand up the messaging architecture everything else runs on
Translate technical proof points (evals, RL environments, model behavior) into content that credibly reaches technical buyers: POVs, case studies, executive bylines, sales narrative
Build sales enablement from scratch — pitch decks, battlecards, objection handling — for a sales team currently working without a CRM or existing collateral
Partner on the front line with sales and a deployment strategist/solutions architect — joining demos and discovery calls to close knowledge gaps in real time as the team ramps
Shape account-based, vertical-specific motions (banking, insurance, retail, legal) in partnership with field and growth marketing, who will already be staffed and running events by fall
Stand up a minimum-viable digital presence (microsite/landing pages) with support from web dev
Use AI tooling aggressively to operate above your weight class — this function doesn't have the headcount yet for a traditional team structure

You Have

7+ years in B2B marketing with a strong product marketing foundation — this is a PMM-first role, not a generalist growth or demand gen seat
Experience partnering with enterprise sales in a high-ACV, complex technical sales motion — comfortable joining live demos and discovery calls, not just producing materials from a distance
Gone zero-to-one before: launched a product, built a function, or served as a founding/solo marketer at an early-stage company
Sold complex technical solutions into traditional, non-tech Fortune 500 enterprises (banking, insurance, retail) rather than exclusively tech buyers
Strong writer and storyteller who gets fluent in genuinely technical material fast
Operates independently with real agency in ambiguous, fast-moving environments — this team is early and self-directed, without a lot of hand-holding infrastructure yet

Bonus Points

Came up at a large, structured company (Salesforce, Google, etc.) before making the jump to a founding marketing role at an AI or technical B2B startup
Fluent in AI tooling as a way of multiplying personal output across content, research, and competitive intel, rather than just a topic you market

We Offer

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.

Compensation Range: $210K - $245K