Manager, Scaled Customer Success

Cacheflow; San Francisco (CA); On-site; USD 180,000 - 240,000; Full time

Benefits offered by this job

Equity

401(k) match

Parental leave

Medical/Dental/Vision

Wellness stipend

Learning stipend

Remote & office access

Flexible PTO

Team events

Referral bonuses

Job summary

Handshake is seeking a customer-focused, operationally minded leader to manage three Mid-Market CSMs and lead our tech-touch digital engagement strategy. The ideal candidate coaches, designs AI-enabled workflows, and builds scalable programs that improve customer health, adoption, retention, and team performance.

You will partner with Product, Sales, Marketing, and other teams to deliver exceptional customer experiences in a fast-growing AI data business.

Qualifications

• 5 to 8 years of relevant experience, including a strong Customer Success background.
• People leadership experience and a track record of coaching and developing CSMs.
• Experience building or managing scaled, tech-touch, or digital Customer Success programs.
• Hands-on experience designing or implementing AI-enabled workflows.
• Strong operational, analytical, and cross-functional collaboration skills.
• Comfort building new programs in an evolving environment.

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

People leadership

Digital CS programs

AI workflows

Operational analytics

Cross-functional collaboration

Job description

About Handshake

Handshake was founded on a simple belief that everyone deserves a path to a great career, regardless of where they went to school or who they know. Today, we power 25 million job seekers, 1 million+ employers, and 1,600 educational institutions.

In 2025, we started Handshake AI and built the fastest-growing AI data business in history. We work directly with frontier AI lab researchers to create evaluations, publish benchmarks, and push the boundary of data. We’ve grown from $0 to ~$1B run rate and pay ~$60M to over 30K individuals every month.

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

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

• Work together with engineers, scientists, operators, and more from Palantir, Meta, Scale AI, and former YC founders

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

About the Role

We are looking for a customer-focused, operationally minded leader to manage three Mid-Market Customer Success Managers and lead our tech-touch digital engagement strategy.

The ideal candidate is a strong coach with experience building scaled Customer Success programs. They are comfortable creating structure in ambiguous environments and have designed AI-enabled workflows that improve customer engagement, team efficiency, or business outcomes. In this role, you'll:

• 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

Desired Capabilities

• 5 to 8 years of relevant experience, including a strong Customer Success background

• People leadership experience and a track record of coaching and developing CSMs

• Experience building or managing scaled, tech-touch, or digital Customer Success programs

• Hands-on experience designing or implementing AI-enabled workflows

• Strong operational, analytical, and cross-functional collaboration skills

• Comfort building new programs in an evolving environment

Extra Credit

• Experience in HR or recruiting technology

• Experience partnering with Account Management or Sales on renewals, retention, and expansion

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.