Remote Lead, Scaled Customer Success & AI-Driven Programs

handshake; New York, California (NY, MO); Hybrid; USD 120,000 - 170,000; Full time

Benefits offered by this job

Equity in a fast-growing company

401(k) match

Parental leave

Fertility benefits

Medical, dental, and vision

Mental health support

Wellness stipend

Learning stipend

Job summary

Handshake seeks a customer-focused, operationally minded leader to manage three Mid-Market CSMs and drive our tech-touch engagement strategy. You will coach the team, set clear expectations, and shape scalable, AI-enabled workflows to improve engagement, retention, and customer health.

You’ll partner with Product, Sales, Marketing and other teams to implement repeatable programs, measure outcomes, and thrive in a data-driven, evolving environment.

Qualifications

• 5–8 years in Customer Success with leadership experience.
• Experience building scaled, tech-touch or digital CS programs.
• Hands-on with AI-enabled workflows and data-driven decisions.

Responsibilities

• Manage, coach, and develop a team of three Mid-Market CSMs.
• Establish rhythms and performance standards for a growing team.
• Build and evolve digital CS motion across onboarding, adoption, and risk.
• Use data to segment audiences and balance human/digital engagement.
• Design AI-enabled workflows to improve efficiency and personalization.
• Create scalable processes and measure impact on health and retention.
• Partner with Product, Sales, Marketing to improve customer experience.
• Turn ideas into repeatable programs amid evolving needs.

Skills

People leadership

CS programs

AI-enabled workflows

Operational analytics

Cross-functional collaboration

Ambiguity management

Job description

Handshake seeks a customer-focused, operationally minded leader to manage three Mid-Market CSMs and drive our tech-touch engagement strategy. You will coach the team, set clear expectations, and shape scalable, AI-enabled workflows to improve engagement, retention, and customer health.

You’ll partner with Product, Sales, Marketing and other teams to implement repeatable programs, measure outcomes, and thrive in a data-driven, evolving environment.