Benefits your employees can talk to.
Health, dental, vision. Competitive prices and AI-supported open enrollment that takes minutes, not weeks.
Ask your AI co-worker to help you find the best benefits for your family.
Open enrollment is the one week a year everyone has questions and nobody has answers. Your co-worker knows the plans, the prices and who is on them.
- Compare plans side by side
- Model the real cost for your family
- Check whether a doctor is in network
- Add a dependent after a life event
- Answer “is this covered?” against your own plan
- Enroll without opening the app
@Winslow which medical plan is best for my family? Two kids, we see an in-network pediatrician a lot and my wife has a specialist every month.
With that much regular care, the higher premium is usually the cheaper year. Comparing the three family plans you are eligible for:
- Aetna PPO Gold — $612/mo, $20 copays, $1,500 deductible. Best fit given your visit count.
- Blue Shield PPO Preferred — $498/mo, $35 copays, $3,000 deductible. Cheaper monthly, more per visit.
- Blue Shield HDHP/HSA — $291/mo, $6,000 deductible, but you can put $8,550 pre-tax into an HSA.
On last year's usage the Gold plan comes out about $900 ahead. Want me to enroll you, or show the math?
Benefits changes are instantly integrated into your payroll.
No manual copying, no double entry, no reconciling two systems at the end of the month. Elect a plan and the deduction is on the next run.
- Employee deductions applied to the next payroll automatically
- Employer contributions costed on the same line
- Mid-cycle changes prorated for you
- One audit trail across benefits and payroll
Everything benefits out of the box.
A network of brokers for competitive plan sourcing. Enrollments and life events managed without tickets. AI-supported because that’s what your employees expect now.
Plan sourcing
Small group, level-funded, large group. Plans for every team size; you don’t change vendors when you outgrow a tier.
Five-minute enrollment
Plan cards presented in Slack. Employee picks, confirms dependents, done.
AI-supported recommendations
Suggested plan based on prior usage, dependents, projected needs. Recommends, doesn’t decide.
Life events
New dependent, address change, qualifying event — triggered by the HRIS, processed without a ticket.
Compliance and Filings
Winslow has your back in all 50 states.
Payroll Integrated
Benefits deductions integrated directly into your payroll runs.
Get a free benefits quote.
Give us a few pieces of information and we’ll email you a quote without having to get on a call!