Head of Scaled Customer Success (AI-Powered)

Handshake; San Francisco (CA); On-site; USD 168,000 - 210,000; Full time

Benefits offered by this job

Equity in company

401(k) match

Parental leave

Mental health support

Learning stipend

Office perks (SF office)

Job summary

Handshake is seeking a customer-focused, operational leader to manage three Mid-Market CSMs and drive our AI-enabled, digital engagement strategy. You will coach a developing team, set clear expectations, and build scalable processes across onboarding, adoption, and risk mitigation.

The role emphasizes using data to tailor human and digital interactions, collaborating with Product, Sales, and Marketing to enhance the customer experience in a fast-growing global platform.

Qualifications

• 5 to 8 years of Customer Success experience
• Leadership experience coaching CSMs
• Experience building or managing scaled, tech-touch, or digital CS programs
• Hands-on experience designing or implementing AI-enabled workflows
• Strong operational, analytical, and cross-functional collaboration skills
• Comfort building new programs in evolving environments

Responsibilities

• Manage, coach, and develop a team of three Mid-Market CSMs
• Establish clear expectations, operating rhythms, and performance standards for a developing team
• Build and evolve our digital Customer Success motion across onboarding, adoption, engagement, and risk mitigation
• Use customer and product data to segment audiences and deliver the right mix of human and digital engagement
• Design and implement AI-enabled workflows that improve efficiency, personalization, and proactive customer support
• Build scalable processes and measure their impact on customer health, adoption, retention, and team performance
• Partner with Product, Sales, Marketing, and other teams to improve the customer experience
• Bring structure to ambiguity and turn ideas into repeatable programs

Skills

Customer success leadership

People leadership

Scaled digi tal CS programs

AI-enabled workflows

Operational analytics

Cross-functional collaboration

Job description

Handshake is seeking a customer-focused, operational leader to manage three Mid-Market CSMs and drive our AI-enabled, digital engagement strategy. You will coach a developing team, set clear expectations, and build scalable processes across onboarding, adoption, and risk mitigation.

The role emphasizes using data to tailor human and digital interactions, collaborating with Product, Sales, and Marketing to enhance the customer experience in a fast-growing global platform.