About the role
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:
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Customer success planning
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Executive stakeholder engagement
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Business outcome alignment
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Expansion opportunities
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Structured executive business reviews
Build a Tiered, AI-Enabled Customer Success Model
Design a scalable coverage strategy that delivers:
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High-touch engagement for strategic customers
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Scaled customer success motions for mid-market accounts
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Automated and AI-powered experiences for long-tail customers
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Improved productivity through AI and automation
Establish Customer Success Best Practices Across the Organization
Create a Customer Success Center of Excellence that will:
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Define customer success methodology
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Standardize health scoring
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Improve retention and expansion programs
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Establish onboarding and engagement frameworks
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Drive operational consistency across multiple business units
What You'll Do
Customer Success Leadership
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Own Net Revenue Retention (NRR)
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Drive enterprise customer retention and expansion
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Lead and develop a high-performing Customer Success team
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Create executive engagement strategies for key accounts
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Improve customer health and adoption outcomes
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Partner closely with Sales, Product, Operations and Executive Leadership
AI-Powered Customer Success
Leverage AI and automation to improve:
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Customer health scoring
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Expansion identification
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Executive business review preparation
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Success planning
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Customer communications
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Team productivity
Customer Voice & Product Alignment
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Build a structured customer feedback process
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Ensure customer insights influence product decisions
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Strengthen collaboration between Customer Success and Product teams
Customer Success Center of Excellence
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Define customer success standards and methodology
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Establish best practices across multiple teams
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Create measurement frameworks and reporting standards
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Influence senior stakeholders through expertise and leadership
What Success Looks Like
Within the first year, you will:
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Improve Net Revenue Retention performance
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Increase expansion within enterprise accounts
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Implement a scalable customer success coverage model
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Introduce AI-driven productivity improvements
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Build stronger customer-to-product feedback loops
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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.
About PowerToFly
PowerToFly is an AI workforce partner that connects organizations with representative experts who build, train, and ship AI. Through a global community of 1.1M+ professionals, more than 75% of whom identify as women, non-binary, or BIPOC, PowerToFly AI helps companies hire AI-fluent professionals for full-time, fractional, and project-based roles, and brings in domain experts to train and evaluate AI models across industries like healthcare, finance, and law.
Because that community spans a wide range of backgrounds and experience levels, the experts PowerToFly AI places and trains reflect the people the resulting AI is built to serve, reducing the risk of blind spots once it reaches production. PowerToFly AI is headquartered in New York, New York, and was founded in 2014.
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Job details
Location
Remote
Funding
Total raised
$37.5M
Last stage
Series B
Investors
What happens next.
No applications, no recruiter spam. Just the intro.
Confirm the fit
A few questions to make sure this role is the right shape for you. Two minutes.
I pitch you to the company
I write the intro, send it to the founder, and handle the back-and-forth.
A meeting lands on your calendar
If they’re a yes, I book the chat. You show up — that’s the whole job-hunt.
