Senior Head of AI Initiatives

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Job Summary:

Handshake AI is a human data labeling business collaborating with leading AI research labs to create innovative human data products. The Head of AI Initiatives will take ownership of product strategy and execution for key areas of the business, leading cross-functional teams to develop systems that match candidates with jobs and automate expert acquisition.

Responsibilities:

• Build a system that deeply understands both people and jobs—then connects them with high accuracy and high intent.

• Capture rich, structured data from candidates and hiring managers via AI-driven interviews.

• Use LLMs to extract, reconcile, and store information in a robust system of record.

• Develop a matching engine that surfaces the best roles for candidates (and vice versa) with clear rationales.

• Enable hiring managers to run automated, rubric-based interviews for top matches.

• Measure and improve signal quality, pass rates, and time-to-hire.

• Build a fully automated, AI-powered growth system to bring niche experts into Handshake AI at scale.

• Identify and scrape expert profiles (e.g., lawyers) from across the internet.

• Enrich profiles with contextual data from social platforms, publications, and networks.

• Personalize outbound outreach using LLMs for tone, content, and relationship context.

• Funnel experts into adaptive onboarding flows—custom landing pages, AI interviews, and targeted CTAs.

• Rapidly experiment with acquisition channels, content formats, and conversion flows.

Qualifications:

Required:

• Proven 0→1 product leadership in high-growth environments.

• Technical fluency—comfortable working closely with engineers, data scientists, and LLM-driven products.

• Experience managing and scaling teams of 5+ people.

• Ability to ruthlessly prioritize and ship quickly without losing quality.

• Exceptional communication—able to work with stakeholders from GTM to research labs.

Preferred:

• HR tech, ATS, or job matching experience.

• Background in cognitive science, linguistics, or education.

• Experience in sales tech, growth automation, or lead generation.

• Hands-on experience with scraping, enrichment, or outbound personalization tools.

• Community building at scale.

Company:

Handshake is a college career network that helps students and recent graduates find their next opportunity. Founded in 2014, the company is headquartered in San Francisco, California, USA, with a team of 501-1000 employees. The company is currently Late Stage. Handshake has a track record of offering H1B sponsorships.

Seniority level

• Seniority level

  Mid-Senior level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Product Management

• Industries

  Software Development

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Inferred from the description for this job

Medical insurance

Vision insurance

401(k)

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