I hate demos! — Everything Winslow does, in one scroll.

I hate demos.

Fine. Here is everything Winslow ships, on one page, in writing, with no salesperson talking over a slide. Read it, hand it to your agent, decide. If you still want a demo at the end, we are happy to do one. If you do not, we've done our job here.

Everything we do, and don't do:

Payroll

  1. Multi-state payroll. Run it, file it, forget it. Off-cycle runs are free, every time.

    • Run payroll in all 50 states.
    • Federal, state, and local tax accounts handled. Hire in a new state, Winslow opens the account before payday.
    • Included

  2. W-2 and 1099 generation

    • Generated, distributed, and e-filed. Year-end is a non-event.
    • Included

  3. Contractor payments

    • 1099 contractors on the same schedule and dashboard as W-2 employees. No second tool.
    • Included

  4. Off-cycle payroll runs

    • Bonuses, corrections, terminations, spot payments. No per-run fee, ever.
    • Free

  5. Garnishment processing

    • Child support, levies, defaulted-loan orders — withheld and routed to the right agency automatically.
    • Included

  6. Direct deposit

    • ACH by default.
    • Included

  7. Anomaly detection on every run

    • Net-pay deltas, missing approvals, unfamiliar deductions — flagged before approval, not after.
    • AI

  8. Approval workflow you can program

    • Approving payroll kicks off an agent process. Out of the box: notifications, exports, anomaly review. Customize with a skill file.
    • AI

  9. Pre-tax deductions

    • FSA, HSA, commuter, parking, dependent care — all handled at the deduction layer.
    • Included

  10. Post-tax deductions

    • Custom withholdings, charitable matching.
    • Included

  11. Time-off accruals on every run

    • PTO, sick, parental, custom leave types — accrued and surfaced on every paystub.
    • Included

  12. Unpaid leave calculations

    • Automatically calculate payroll adjustments for unpaid leave
    • Included

  13. Reimbursements

    • Expense, mileage, equipment, per-diem — paid through payroll or off-cycle.
    • Included

  14. Paystub access in Slack

    • Employees DM Winslow, get their paystub. No portal login.
    • Included

  15. We do not support hourly workers at this time

    • We manage payroll for salaried employees in the United States only at this time
    • Included

Benefits

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.

  1. Broker network for plan sourcing

    • A network of brokers shops your plans for competitive pricing — small group, level-funded, large group.
    • Included

  2. Health insurance — small group, level-funded, large group

    • Plans for every team size. You don't change vendors when you outgrow a tier.
    • Included

  3. Dental and vision

    • Standard ancillary lines, sourced and administered.
    • Included

  4. Open enrollment in Slack

    • Plans presented as cards in the thread. Employee picks, confirms dependents, done. Five minutes.
    • AI

  5. Plan recommendations

    • Agent analyzes the employee's prior usage, dependents, and projected needs. Suggests, doesn't decide.
    • AI

  6. Life-event processing

    • New dependent, address change, qualifying event — triggered by HRIS, processed without a ticket.
    • Included

  7. Compliance and Filings

    • Winslow has your back in all 50 states.
    • Included

  8. Carrier integrations

    • Direct connections to major carriers. Enrollments and demographic changes sync without EDI tickets.
    • Included

  9. Renewal calendar with quotes

    • 60 / 30 / 15 days out — options sourced, recommendations sent, communications drafted.
    • Included

  10. Payroll Integrated

    • Benefits deductions integrated directly into your payroll runs.
    • Included

HRIS

An AI-native architecture for employee records, documents, payroll and PTO. Designed for builders and agents.

  1. Employee records with custom fields

    • Add fields, custom views, formulas. No vendor data model imposed.
    • Included

  2. Custom employee types

    • W-2, 1099, intern, foreign contractor, advisor — define your own with their own fields and workflows.
    • Included

  3. Org structure

    • Reporting lines, dotted lines, multiple managers. Real-time headcount and span-of-control.
    • Included

  4. Onboarding workflows

    • Written in plain English. Same workflow scales from 10 to 500 EE.
    • AI

  5. Offboarding workflows

    • Equipment return, access revocation, final pay, COBRA — kicked off the moment termination lands.
    • Included

  6. PTO tracking

    • Accruals, balances, requests, approvals — surfaced in Slack and on every paystub.
    • Included

  7. Custom leave types

    • Parental + grandparental + caregiving + bereavement + sabbatical — define them in a sentence.
    • Included

  8. Document storage

    • Offer letters, signed handbooks, I-9s, visa docs. Versioned, audit-logged, searchable.
    • Included

  9. E-signature for HR documents

    • Native, audit-logged, court-admissible.
    • Included

  10. Real-time reporting

    • Headcount, comp distribution, retention by team, attrition. Pivot-able, exportable.
    • Growth+

  11. Open data model

    • Real, writable database. Read it, write it, build on it. No vendor lock on your data.
    • Included

  12. Headcount planning

    • Open reqs, projected starts, replacement vs incremental. Linked to comp bands.
    • Growth+

  13. Manager dashboards

    • Direct report list, comp history, time-off requests, recent changes. Lives in Slack, mirrored in admin UI.
    • Included

Tax & compliance

Notices opened, registrations filed, deadlines hit. Agents handle 10,000+ jurisdictions so you don't.

  1. State tax registration

    • SUI, withholding, unemployment accounts opened automatically when you hire in a new state.
    • AI

  2. Federal, state, local filings

    • 941, 940, W-2s, W-3s, state quarterly returns — on time, every cycle.
    • Included

  3. Tax notice resolution

    • Agent reads the notice, classifies it, acts. You see a summary, not a stack of envelopes.
    • AI

  4. SUI rate updates

    • Captured from the state, applied to the next run, back-corrected if applicable.
    • Included

  5. I-9 verification

    • E-Verify-compatible workflow, document collection, audit trail.
    • Included

  6. Workers' comp setup

    • Pay-as-you-go where available; carrier reporting otherwise.
    • Included

  7. EEO-1 reporting

    • Generated from the HRIS, ready to file at the deadline.
    • Growth+

  8. ACA 1095-C reporting

    • Generated, distributed, e-filed.
    • Included

  9. Multi-state compliance per locality

    • San Francisco HCSO, Seattle PTO, NYC salary disclosure — handled at the locality level, not just the state.

Slack and Claude

The 95% of your team that doesn't need to log into an HR portal — doesn't.

  1. DM Winslow anything

    • PTO, paystubs, benefits, onboarding tasks, policy lookup. Sourced from your data and policies, not the open web.
    • AI

  2. Employee Q&A

    • Fully context-sensitive employee Q&A against policies, procedures, benefits plans, and their own data.
    • AI

  3. @winslow-hr human escalation

    • Real HR experts answer in the same thread. Bundled with Winslow First.
    • First

  4. Inline onboarding

    • Tasks ask, employee replies in-thread, HRIS updates. No "please log into the portal" emails.
    • Included

  5. PTO requests

    • Conversational request. Manager approves with one click in the thread.
    • Included

  6. Open enrollment

    • Plan cards rendered in chat. Five-minute flow per employee.
    • Included

  7. Document collection

    • Missing W-4? Winslow asks, employee uploads in-thread, HRIS updates.
    • Included

  8. Custom skill files rendered in-chat

    • Your own tools launch inline as generative UI — same pattern as Claude artifacts or ChatGPT canvas.
    • AI

  9. Analytics on questions

    • HR sees what employees are asking. Trending topics, unanswered questions, time-to-resolution.
    • Growth+

Architecture for agents

If you're here for a reason, this is probably it. MCP, skill files, webhooks. Your agents drive Winslow as a first-class consumer.

  1. Public MCP server

    • Claude, ChatGPT, Cursor, Lovable, Bolt — all read and write Winslow through the same MCP. No bespoke integrations.
    • AI

  2. Skill files for custom workflows

    • Drop them into your Winslow workspace. The Slack employee chat runs them like built-in features.
    • AI

  3. Webhooks for every lifecycle event

    • Hire, terminate, promote, comp change, leave request — all fire to your stack.
    • Included

  4. REST + GraphQL API

    • Standard auth, paginated, versioned. The MCP is a wrapper on this; nothing is hidden.
    • Included

  5. Writable system of record

    • No black-box objects. Read, write, audit, export. Your HR data is yours.
    • Included

  6. Custom menu items in admin UI

    • Tools you build externally register as menu items inside Winslow. Lives where the team already works.
    • AI

  7. Generative-UI tools in chat

    • When an employee says "I want to do X," Winslow launches your tool inline. Same pattern as Claude artifacts.
    • AI

  8. Vibe-code support

    • Point Lovable, Cursor, Bolt at the MCP, build a custom HR app in an afternoon. We do not ship it for you on purpose.
    • AI

  9. Native audit log on every action

    • Agent-driven actions are auditable as first-class events. Same trail as human actions.
    • Included

  10. <code>/llms.txt</code> + <code>/for-your-agent</code> routes

    • Machine-readable canonical summary at the edge. Your agent reads it in one fetch, no scraping required.
    • Included

Security & trust

Boring on purpose. The page your security team sends back with no questions.

  1. SOC 2 Type II

    • Annual audit. Report available on request behind a short form.
    • Included

  2. Encryption in transit and at rest

    • TLS 1.3, AES-256. Keys rotated quarterly.
    • Included

  3. Role-based access control

    • Granular roles. Audit on every permission change.
    • Included

  4. Full audit log export

    • Every employee-data change. Exportable to your SIEM.
    • Included

  5. Data residency

    • US-only.
    • Scale

Winslow Forward

A forward-deployed People Ops Engineer comes with the Scale tier. Not a consultant. Not an implementation partner. Part of the product.

  1. Dedicated engineer from day one

    • No 12-week search, no $200K hire, no attrition risk.
    • Scale

  2. Platform setup around your company

    • Org structure, policies, comp philosophy, onboarding rhythm — configured to fit, not to template.
    • Scale

  3. Agentic workflows written for you

    • Payroll reconciliation, comp reviews, custom leave types, onboarding sequences, manager dashboards.
    • Scale

  4. Skill-file training for your team

    • By end of Q1, your People team can vibe-code their own workflows.
    • Scale

  5. Quarterly business reviews

    • What's working, what's next, what to build. Your engineer surfaces and proposes.
    • Scale

  6. Incentivized to make you self-sufficient

    • Different from a consultant — your Forward engineer wins when your team builds their own.
    • Scale

Pricing

Usage-based pricing, starting at $40/mo. Pay for what you use, not for who you hired — 10–30× cheaper than legacy platforms over three years. No per-employee-per-month subscription, ever.

One-time

Monthly

Winslow Forward — a forward-deployed PeopleOps engineer — starts at an additional $5,000/mo.

Screenshots

A look at the actual product. Click any shot to open it full-size.

What we don't do

Honest list. If one of these is a dealbreaker, save us both a call.