Head of Scaled Customer Success & Digital Engagement

Handshake; San Francisco (CA); On-site; USD 120,000 - 150,000; Full time

Benefits offered by this job

Health Insurance

Fertility & family forming

LGBTQ+ coverage

Mental health benefits

Tax-advantaged benefits

Life & disability insurance

401k match

Equity program

Financial planning services

Learning & development stipend

Community ERG support

Parental leave

Flexible time off

Sabbatical

Volunteer time off

Job summary

Handshake in San Francisco seeks a customer-focused, operations-minded leader to manage three Mid-Market CSMs and shape the tech-touch digital engagement strategy. You will coach the team, set rhythms, and drive performance while partnering with Product, Sales, and Marketing to improve onboarding, adoption, and retention.

The role emphasizes building AI-enabled workflows, data-driven segmentation, and scalable processes to elevate customer health and team outcomes in a fast-paced environment.

Qualifications

• Strong coach with experience building scaled Customer Success programs.
• Comfort creating structure in ambiguous environments and turning ideas into repeatable programs.
• Experience designing or implementing AI-enabled workflows to improve engagement.

Responsibilities

• Manage, coach, and develop a team of three Mid-Market CSMs.
• Establish clear expectations, operating rhythms, and performance standards.
• Build and evolve the digital CS motion across onboarding, adoption, engagement, and risk mitigation.
• Use customer and product data to segment audiences and tailor human/digital engagement.
• Design and implement AI-enabled workflows to improve efficiency and personalization.
• Build scalable processes and measure impact on 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

Team leadership

Coaching

Data-driven

Cross-functional

AI workflows

Process design

Customer focus

Analytics

HR experience

Job description

Handshake in San Francisco seeks a customer-focused, operations-minded leader to manage three Mid-Market CSMs and shape the tech-touch digital engagement strategy. You will coach the team, set rhythms, and drive performance while partnering with Product, Sales, and Marketing to improve onboarding, adoption, and retention.

The role emphasizes building AI-enabled workflows, data-driven segmentation, and scalable processes to elevate customer health and team outcomes in a fast-paced environment.