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combining automation and intelligence to transform insurance distribution and bring speed, structure, and clarity to outdated workflows.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
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
