Head of Engagement Management, Handshake AI

About Handshake

Handshake is the career network for the AI economy. 20 million knowledge workers, 1,600 educational institutions, 1 million employers (including 100% of the Fortune 50), and every foundational AI lab trust Handshake to power career discovery, hiring, and upskilling, from freelance AI training gigs to first internships to full-time careers and beyond. This unique value is leading to unparalleled growth; in 2025, we tripled our ARR at scale.

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

• Work hand-in-hand with world-class AI labs, Fortune 500 partners and the world’s top educational institutions

• Join a team with leadership from Scale AI, Meta, xAI, Notion, Coinbase, and Palantir, among others

• Build a massive, fast-growing business with billions in revenue

About the Role

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.

You will be responsible for:

• 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.

What success looks like in the first 6 to 12 months:

• The Engagement team is operating against a clear strategy and playbook, with consistent standards across accounts and managers.

• Key business metrics for Handshake AI, such as NRR, expansion, and time to value, have improved meaningfully across your portfolio.

• Our largest and most strategic customers see Handshake AI as a critical partner, with strong executive relationships and clear, referenceable wins.

• Sales, Operations, Product, and company leadership see you as the owner of our AI customer book, and regularly involve you in the most important decisions.

You will work closely with:

• Engagement Managers and other GTM leaders to set strategy, support execution, and raise the bar on customer outcomes.

• Sales leadership on account planning, deal strategy, forecasting, and expansion motions.

• Handshake AI Operations and Strategic Projects leadership to align delivery capacity and quality with customer commitments.

• Product and Engineering leadership to provide structured feedback from the field and influence roadmap priorities.

• Executive leadership on overall Handshake AI strategy, planning, and investor and customer narratives.

What You Will Bring

Experience:

• 8+ years in customer facing, high ownership roles in SaaS, AI, data, or technical services, with 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.

This role works well for people who:

• Want to own a book of business at the company level and be directly accountable for revenue, adoption, and customer outcomes

• Enjoy leading and coaching senior customer facing talent, setting a high bar, and giving clear, direct feedback

• Can move easily between executive relationship management and deep dives on programs, metrics, and risks

• Are comfortable with high visibility, high pressure situations and making decisions with incomplete information

• Like building playbooks and systems, not just running individual accounts

It is not a good fit if you need fixed hours, narrow scope, or heavy structure. There are periods of high intensity, including occasional early or late calls across time zones. Priorities can change quickly and you will often be the person asked to solve the hardest customer problems.

People in this role often come from:

• Management consulting at top tier firms, with significant client leadership and project ownership

• Strategy and operations or bizops roles at early stage or high growth startups

• Customer facing leadership roles in SaaS or AI / data companies (engagement management, customer success, solutions, or similar)

• Investment banking or private equity backgrounds that transitioned into operating or client facing roles

Prior experience in AI is helpful but not required.

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.