Customer Success Manager

About Pathwork

Pathwork is redesigning life & health insurance jobs for the AI age. We believe the 2.5M professionals in the $1T life and health insurance industry don’t need better tools; they need a new operating system.

Pathwork’s first solution streamlines the pre-application process in the life and health insurance industry. By removing friction from early case work, brokers can operate with greater speed, accuracy, and precision, giving them a competitive edge like never before.

We’ve already proven it:

• 60+ top brokerages and national carriers use Pathwork

• Active pilots with multiple top-10 insurance companies

• 150%+ QoQ growth, every quarter since launch
  

Pathwork was built from day one as AI-native, combining automation and intelligence to transform insurance distribution and bring speed, structure, and clarity to outdated workflows.

Why Pathwork

• Category-defining product already in use by national brokerages and insurers

• Funding from top VCs

• Deep founder experience: Work closely with experienced founders who’ve built and scaled companies from zero to exit in insurance and AI

• Early team, high ownership: You’ll shape the brand, the function, and the category

• High-Trust & Long-term Oriented: Grow with a team that values trust, authenticity, learning, and lasting impact. Your contributions will help shape our product, culture, and long-term legacy

About the Role

We’re hiring our first Customer Success Manager, a strategic and hands-on builder who can make an impact from day one. You’ll report to the Head of Revenue and work alongside the Founders, Sales, and Product teams to create a category-defining customer experience.

This role is open from Customer Success Associate through Senior Customer Success Manager, depending on your experience. It’s for a strong individual contributor, with the option to grow into leadership if that’s the path you want to take.

You’ll own relationships with SMB and mid-market brokers, ensure successful onboarding and adoption, and help shape how Pathwork delivers value across our customer base.

What You’ll Own

Customer Onboarding & Adoption

• Lead onboarding programs for new SMB and mid-market brokers

• Build and evolve playbooks for training and enablement to drive adoption
  

Customer Relationships & Retention

• Serve as the trusted advisor and primary point of contact for brokers and carriers

• Monitor account health, resolve issues, and proactively prevent churn

• Partner with GTM and Product to ensure customer feedback shapes the roadmap
  

Growth & Expansion

• Identify opportunities for upsell/expansion across accounts

• Support Sales with renewals, case studies, and broker references
  

Contribute to the Function

• Help refine customer success processes and metrics

• Partner with Marketing and Product to create scalable customer resources

• Option to grow into leadership, with the opportunity to hire, coach, and inspire a future CS team

You Might Be a Fit If You…

• Have 2-6+ years of experience in Customer Success or Account Management, ideally at an early-stage startup

• Experience working with SMB/mid-market clients, with insurance or financial services strongly preferred

• Thrive in chaos, energized by building process while scaling growth and not intimidated by ambiguity

• Like getting your hands dirty, with no task too small whether it’s jumping on a customer support call or drafting a one-pager

• Strong verbal and written communication skills, especially with technical and regulated audiences

• Want to be part of something bigger, shaping not just a function but a category, a company, and the future of insurance distribution

• Major plus: experience working in insurance or for software supporting the insurance industry

• Bonus: comfortable leading renewals/expansion conversations and collaborating with sales
  

What You’ll Get

• Competitive comp + meaningful equity

• Employee-centric benefits including:

  • High 401K match and FSA program

  • Modern, employer-paid health benefits designed to support you on your terms

• Hybrid culture: NYC & SF offices, or remote for the right candidate