✦ Pricing
Choose the Winston tier that matches your stage.
Choose the operating layer for your stage. Each tier begins with a one-time activation fee, followed by separate monthly service after launch.
Fast comparison
Venture is the lean launch, Executive adds AI calling and more channels, and Enterprise installs the full white-glove operating layer.
Lean launch
Venture
Best when you want Winston handling outbound, marketing, and reporting without extra hires.
Growth stage
Executive
Best when you need more channel coverage, AI calling, and faster support.
White-glove
Enterprise
Best when Winston is taking over a larger revenue and operations machine.
Winston Venture
Launch Winston without building a team first.
Built for
For founders who need outbound, marketing, and core operating support live fast.
One-time activation
$2,500
Ongoing monthly service
$350/mo
Initial commitment
$2,850
Activation covers onboarding, integrations, campaign setup, and launch support. Monthly service is purchased separately after activation.
- Outbound email engine + lead follow-up
- Meta ads + AI content production
- Executive Hub, reporting, and launch support
View full feature breakdown
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
Opens a secure activation checkout in a new tab for the one-time $2,500 setup fee. Monthly service is separate: review $350/mo service checkout
✦ Most Popular
Winston Executive
Add AI calling and broader channel coverage.
Built for
For growth-stage operators who need Winston driving a bigger pipeline and faster response times.
One-time activation
$5,000
Ongoing monthly service
$999/mo
Initial commitment
$5,999
Activation covers onboarding, integrations, campaign setup, and launch support. Monthly service is purchased separately after activation.
- Everything in Venture, plus AI calling
- More channel coverage across sales and marketing
- Deeper finance, recruiting, and priority support
View full feature breakdown
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
Opens a secure activation checkout in a new tab for the one-time $5,000 setup fee. Monthly service is separate: review $999/mo service checkout
✦ White Glove
Winston Enterprise
Install the full white-glove operating layer.
Built for
For established companies ready to hand Winston a larger share of revenue and operations.
One-time activation
$10,000
Ongoing monthly service
$1,800/mo
Initial commitment
$11,800
Activation covers onboarding, integrations, campaign setup, and launch support. Monthly service is purchased separately after activation.
- Unlimited agents, calling, and deeper automation
- CRM ownership, strategy reporting, and client portals
- Dedicated success, legal, and white-glove support
View full feature breakdown
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
Opens a secure activation checkout in a new tab for the one-time $10,000 setup fee. Monthly service is separate: review $1,800/mo service checkout
Shared Platform Terms
Every tier includes Winston's revenue share: 15% in months 1–6, then 10% from month 7 onward, capped at $10,000 per month.
Built to be accountable
An AI CEO with a real operating foundation.
Winston is designed as an AI CEO and operator, with concrete business modules behind it—not a collection of disconnected tools. The platform brings sales, marketing, incorporation setup, the Executive Hub, reporting, and client portal access into one operating layer.
Founded by Justin Joslin
Justin is a Disabled Army Veteran who medically retired in 2020 and an experienced business coach and consultant. Winston was built for founders who need serious operating infrastructure without assembling it alone.
Quick fit check
Know whether Winston fits before you activate.
Winston is for
Founders and lean teams who want one operating layer for sales, marketing, launch workflows, and business visibility.
Winston is not for
Someone looking for a single self-serve app, a passive investment, or guaranteed business, legal, or financial results.
✦ Every Plan
All Plans Include
- Business Analytics
- Real-time dashboard with key performance metrics
- Winston AI Co-Founder
- Direct access to your AI business partner
- Contract Templates
- Legal doc library + basic document review
- Multi-State Payroll
- Tax filing handled across all 50 states
- Email Marketing
- Campaign creation, scheduling, and analytics
- Onboarding Session
- Dedicated setup call to get you running fast
- Client Dashboard
- Unified reporting portal for your business
- Revenue Share
- 15% for months 1–6, then 10% — capped at $10K/mo
✦ Optional Add-Ons
Add extra capacity when you need it
Keep your plan choice simple first, then layer on add-ons later.
Select your tier (optional)
Estimated Monthly Cost
Select a tier and check add-ons to build your estimate
✦ Start Today
Choose the tier that fits today. Winston can scale with you later.
Start with the operating layer you need now, then add more capacity only when the business requires it.
Questions? Read the FAQ or contact Winston.