Senior Product Manager, Benefits & PEO (Multiple Roles) at Gusto

This role is ideal for senior product managers with 5+ years of experience who thrive in complex, regulated domains like Fintech, Insurtech, or HR Tech. They are hiring for three distinct tracks: **PEO Growth** (0→1 building), **Workers' Comp** (Insurance vertical expertise), and **Benefits Admin** (Systems thinking/AI-driven internal tools). If you enjoy navigating ambiguity and blending product judgment with AI-native workflows, this lean team offers high ownership. The compensation is highly competitive, scaling up to $230,000 for high-cost-of-living areas like SF, NYC, and Seattle. While the role is listed as remote-friendly across numerous "Centers of Gravity" in the US and Canada, those near main hubs (Denver, SF, NYC) should expect a hybrid 2-3 day office schedule. This is a strategic "big bet" for the company, offering the stability of a $500M+ revenue business with the fast-paced impact of a new product launch. **You might be a good fit if you...** * Have a track record of shipping products in regulated spaces like payroll, taxes, or insurance. * Are a "boundaryless builder" comfortable with technical architecture and operational workflows. * Want to use AI tools to automate manual processes and accelerate product delivery. * Can translate complex carrier integrations and compliance needs into simple customer experiences.