Software gets you 90% of the way. The last 10% — picking the right health plans, registering tax accounts in five new states, writing a termination letter, designing onboarding that scales — needs a human who has done it before. Winslow ships with one.
For 1–50 employees. Especially the ones rolling off a PEO onto their first standalone platform.
You're too small for a full-time HR person. You're too small even for a fractional. But you still need help with the annoying-but-essential things that come with running payroll — tax accounts in employee states, health plan choices, that first termination, the compliance questions you've never had to think about. Winslow First bundles a dedicated HR expert with the platform — 50 hours a year, free, included with your subscription.
For larger teams ready to implement agentic HR — and have it run across Winslow plus the other systems where your data actually lives.
A dedicated agentic PeopleOps Lead joins your team and writes the workflows you'd have built if you had hired six engineers two years ago. Not just on top of Winslow — they automate across Slack, Notion, Linear, Snowflake, your ATS, your warehouse, wherever the data lives. They train your People team to extend the skills themselves, and stay close for as long as you need them.
Forward is a paid add-on — unlike Winslow First's bundled HR expert, a dedicated PeopleOps Lead is priced separately per engagement (included at the Winslow Scale tier). You're hiring a person, not a bundled benefit, so we charge like it.
We love AI as much as anyone but the human touch is still important in HR.