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Handshake Logo Handshake · IT - Administration

Head of Engagement Management

United States, San Francisco 188000.00 - 235000.00 USD / Year · Job Posted February 20, 2026
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Job Description

As Head of Engagement Management, Handshake AI, you will run the Engagement function that owns our largest and most strategic customers end to end. You will lead a multi layered team of Engagement Managers and ICs, and be accountable for revenue, adoption, and retention across a high impact portfolio. You will operate like the GM for our AI customer book of business: setting the strategy for how we land, expand, and retain customers, and making sure we execute at a very high bar. You will work directly with senior leaders at Handshake and C level counterparts at customers, in an environment that is high visibility, high pressure, and fast changing.

Job Responsibility

  • Leading and scaling the Engagement Management team, including hiring, managing, and developing Engagement Managers who own flagship Handshake AI accounts
  • Setting the engagement strategy and operating model, including segmentation, coverage, playbooks, and standards for how we work with frontier labs and enterprise customers
  • Driving consistent, high quality execution of customer programs, from onboarding and implementation through production deployments, expansions, and renewals
  • Owning core customer health and performance metrics, such as NRR, churn, adoption, deployment timelines, and executive satisfaction, and using data to drive decisions
  • Partnering with leadership on territory planning, deal strategy, and expansion motions, and ensuring seamless pre to post sales handoffs
  • Acting as an escalation and executive sponsor for our most important and complex customers when stakes and expectations are highest
  • Working with Operations, Product, and Engineering to translate customer needs into roadmap priorities, operational improvements, and new offerings

Requirements

  • 8+ years in customer facing, high ownership roles in SaaS, AI, data, or technical services
  • At least 3+ years leading teams
  • Proven success managing and scaling customer facing teams such as engagement management, customer success, consulting, or solutions
  • Track record owning a significant book of business with clear responsibility for renewals, expansion, and customer outcomes
  • Experience working directly with senior stakeholders (VP and C level) at large, complex customers, including in high pressure situations

Nice to have

Prior experience in AI is helpful but not required

What we offer

  • Equity in a fast-growing company
  • 401(k) match, competitive compensation, financial coaching
  • Paid parental leave, fertility benefits, parental coaching
  • Medical, dental, and vision, mental health support, $500 wellness stipend
  • $2,000 learning stipend, ongoing development
  • Internet, commuting, and free lunch/gym in our SF office
  • Flexible PTO, 15 holidays + 2 flex days
  • Team outings & referral bonuses
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