✦ Pricing
Everything Your Business Needs.
A Fraction of What You'd Pay Elsewhere.
One platform. All your services. Built-in AI. Winston replaces 12 separate vendors and saves you thousands every month.
15% revenue share mo 1–6 · 10% mo 7+ · capped at $10K/month — included on every tier
✦
Winston Venture
Launch your AI-powered business
Get started for
then $350/mo ongoing
Save 15% — $3,600/yr with annual billing
AI Agents
- 3 agents (Invoicing, Payroll, HR Assistant)
- Custom agent builder
- API access
AI Sales Calls
- Up to 50 calls/month (Vapi)
- Custom voice + call recording
- AI outbound multi-channel
Accounting
- Monthly P&L, balance sheet, cash flow
- AP/AR management
- CFO-level advisory + tax planning
Payroll & HR
- Up to 10 employees, multi-state
- Benefits administration
- International payroll + equity mgmt
Marketing
- Email campaigns + 2 social channels
- SEO + paid ads management
- PR, events, dedicated content team
Support & Legal
- Email + chat · 4-hour SLA
- Contract templates + doc review
- Contract negotiation + M&A support
After setup, subscribe for $350/mo
✦ Most Popular
Winston Executive
Scale with the full AI executive suite
Get started for
then $999/mo ongoing
Save 15% — $10,200/yr with annual billing
AI Agents
- 10 agents (Sales, Marketing, CS, Inventory, Proposal, Compliance, Reporting + more)
- Custom agent builder
- API access
AI Sales Calls
- Up to 200 calls/month
- Custom voice + call recording
- Custom accent/language
Accounting
- Full accounting + real-time cash flow
- AP/AR management
- Multi-entity consolidation + audit support
Payroll & HR
- Up to 50 employees, multi-state
- Benefits administration + recruiting support
- International payroll + C-level search
Marketing
- Email + SMS + all social channels
- SEO + paid ad management
- PR + events + full-funnel content team
Support & Legal
- Priority phone · 1-hour SLA
- Contract negotiation + M&A support
- General counsel + litigation
After setup, subscribe for $999/mo
✦ White Glove
Winston Enterprise
Full white-glove AI business ownership
Get started for
then $1,800/mo ongoing
Save 15% — $18,400/yr with annual billing
AI Agents
- Unlimited agents + custom builder
- White-label + API access
- Email + CRM integration
AI Sales Calls
- Unlimited calls — AI outbound multi-channel
- Custom voice + accent + language
- CRM sync + call analytics
Accounting
- CFO-level advisory + tax planning
- Multi-entity consolidation + audit support
- Monthly strategy report
Payroll & HR
- Unlimited employees, international payroll
- Equity mgmt + 409A valuation
- C-level executive search + org design
Marketing
- Everything + full-funnel strategy
- PR, events, dedicated content team
- Client portals + Executive Hub access
AI Trading
- Investiquant AI-powered algorithmic trading module
- Requires minimum $60,000 on deposit in Stripe to activate
- Corporate treasury automation + portfolio strategy
Support & Legal
- Dedicated success manager · 15-min SLA
- General counsel + litigation support
- Regulatory compliance + white-glove onboarding
After setup, subscribe for $1,800/mo
All tiers include Winston's revenue share: 15% of platform revenue months 1–6 · 10% months 7+ · capped at $10,000/month
✦ Every Plan
All Plans Include
Revenue share: 15% mo 1–6 · 10% mo 7+ · $10K/mo cap
Business analytics dashboard
Winston AI Co-Founder access
Contract templates + basic doc review
Multi-state payroll tax filing
Email marketing campaigns
Dedicated onboarding session
Client dashboard + reporting
✦ Power-Ups
Add-On Menu
Stack any add-on onto any tier. Add or remove monthly.
Select your tier (optional)
Estimated Monthly Cost
Select a tier and check add-ons to build your estimate
✦ Questions
Frequently Asked Questions
✦ Start Today
Stop paying 12 vendors. Start paying one.
Every month you wait is money left on the table. Winston saves more than it costs — starting day one.
Questions? Read the FAQ or visit the free consultation page.