Head of Customer Success

PowerToFly.com; United States; Remote; USD 180,000 - 240,000; Full time

Benefits offered by this job

Remote work

Healthcare

Retirement plan

Parental leave

Unlimited PTO

Mentorship opportunities

Job summary

PowerToFly.com is seeking a Head of Customer Success to lead a strategic transformation focused on customer growth, retention, and AI-enabled productivity. This senior role has high visibility and direct ownership of CS outcomes.

You will design a tiered, AI-enabled model, establish a CS Center of Excellence, and drive executive engagement with enterprise customers while aligning with Sales, Product, and Operations. Remote-first, global team.

Qualifications

• Proven track record leading customer success teams
• Experience building enterprise growth and retention programs
• Strong collaboration with Sales, Product and Ops teams

Responsibilities

• Own Net Revenue Retention (NRR) and drive expansion in enterprise accounts
• Lead and develop a high-performing CS team
• Create executive engagement strategies for key customers
• Develop AI-enabled processes for health scoring and productivity
• Champion best practices across the organization and establish a CS Center of Excellence

Skills

Leadership

Strategic planning

Customer success

Executive engagement

Stakeholder mgmt

Tools

CRM systems

Job description

We are partnering with a rapidly growing global B2B SaaS organization that develops technology used by millions of users worldwide. The company serves a diverse customer base ranging from individual developers and startups to large enterprise organizations.

As the business continues to scale its enterprise customer success function, it is seeking a Head of Customer Success to lead a strategic transformation focused on customer growth, retention, operational excellence, and AI-enabled productivity.

This is a highly visible leadership role with significant influence across the business and direct ownership of customer success outcomes.

The business is entering a new phase of growth and is focused on three strategic priorities:

Shift from Renewals to Growth Partnerships

Move beyond transactional renewal management and build a proactive customer success model focused on:

• Customer success planning
• Executive stakeholder engagement
• Business outcome alignment
• Expansion opportunities
• Structured executive business reviews

Build a Tiered, AI-Enabled Customer Success Model

Design a scalable coverage strategy that delivers:

• High-touch engagement for strategic customers
• Scaled customer success motions for mid-market accounts
• Automated and AI-powered experiences for long-tail customers
• Improved productivity through AI and automation

Establish Customer Success Best Practices Across the Organization

Create a Customer Success Center of Excellence that will:

• Define customer success methodology
• Standardize health scoring
• Improve retention and expansion programs
• Establish onboarding and engagement frameworks
• Drive operational consistency across multiple business units

What You'll Do

Customer Success Leadership

• Own Net Revenue Retention (NRR)
• Drive enterprise customer retention and expansion
• Lead and develop a high-performing Customer Success team
• Create executive engagement strategies for key accounts
• Improve customer health and adoption outcomes
• Partner closely with Sales, Product, Operations and Executive Leadership

AI-Powered Customer Success

Leverage AI and automation to improve:

• Customer health scoring
• Expansion identification
• Executive business review preparation
• Success planning
• Customer communications
• Team productivity

Customer Voice & Product Alignment

• Build a structured customer feedback process
• Ensure customer insights influence product decisions
• Strengthen collaboration between Customer Success and Product teams

Customer Success Center of Excellence

• Define customer success standards and methodology
• Establish best practices across multiple teams
• Create measurement frameworks and reporting standards
• Influence senior stakeholders through expertise and leadership

What Success Looks Like

Within the first year, you will:

• Improve Net Revenue Retention performance
• Increase expansion within enterprise accounts
• Implement a scalable customer success coverage model
• Introduce AI-driven productivity improvements
• Build stronger customer-to-product feedback loops
• Establish a Customer Success Center of Excellence

What PowerToFly.com Has to Offer

PowerToFly supports a fully remote team and core coverage with country specific benefits. This may include health care, a retirement savings plan, parental and adoption leave and perks such as self-directed budgets to support learning and growth. We also offer unlimited personal time off and mentorship opportunities.