Director of Marketing, Enterprise AI

Handshake was founded on the 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 launched Handshake AI and built the fastest-growing AI data business in history, working directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to a ~$1B run rate and pay ~$60M to over 30K individuals every month.

About the Role

Handshake built the eval and human-data infrastructure that frontier AI labs rely on to improve their models and agents. We deliver capabilities from RL environments to expert-in-the-loop eval construction and post-training systems. Now, we are extending this infrastructure to 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 effectively in production.

This is the founding marketing role for this new line of business—a product marketing role focused on positioning, technical narrative, and sales partnership. You will work directly with company leadership, leveraging Handshake’s marketing org, brand, and infrastructure while building the Enterprise AI motion from the ground up. Responsibilities include:

• Own positioning and messaging end-to-end—define the ICP, build the competitive narrative, and establish the messaging architecture.
• Translate technical proof points (evals, RL environments, model behavior) into content for technical buyers, including POVs, case studies, executive bylines, and sales narratives.
• Build sales enablement from scratch—pitch decks, battlecards, objection handling—for a sales team currently operating 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.
• Shape account-based, vertical-specific motions (banking, insurance, retail, legal) in partnership with field and growth marketing.
• 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 in a lean, fast-moving environment.

Requirements

• 7+ years in B2B marketing with a strong product marketing foundation—this is a PMM-first role.
• Experience partnering with enterprise sales in a high-ACV, complex technical sales motion—comfortable joining live demos and discovery calls.
• 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 can quickly master genuinely technical material.
• Operates independently with agency in ambiguous, fast-moving environments—this team is early and self-directed.

Bonus Points

• Came up at a large, structured company (Salesforce, Google, etc.) before transitioning to a founding marketing role at an AI or technical B2B startup.
• Fluent in AI tooling as a way to multiply personal output across content, research, and competitive intel.

Benefits

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 coverage; mental health support; $500 wellness stipend.
• Growth: $2,000 learning stipend, ongoing development opportunities.
• Remote & Office: Internet stipend, commuting benefits, and free lunch/gym in our SF office.
• Time Off: Flexible PTO, 15 holidays + 2 flex days.
• Connection: Team outings and referral bonuses.

Pay

Compensation range: $210K - $245K.