What is the activation fee versus the monthly fee?
Activation is the one-time charge that starts setup and launch. The monthly fee is the ongoing cost of your selected Winston plan after activation. Both amounts are shown before checkout.
The Business AI Butler · A Joslin Enterprises Innovation
Put an AI CEO in charge of revenue and operations.
Winston installs the operating system, launches the workflows, and runs the daily execution so you can scale without adding more headcount first.
Activation from $2,500Go live in as little as 7 business daysNo extra hires required to launch
One operating layer
What Winston takes over
Sales
Prospecting, follow-up, and lead handling without a sales hire.
Marketing
Campaigns, content, and ad execution from one coordinated command.
Operations
Reporting, payroll, HR, and launch workflows in the same system.
Buying path: choose a tier, complete activation, and Winston launches the system for you.
Start with Venture at $2,500 activation, then move into monthly service after setup.
Process
How Winston Works
Three steps from sign-up to a fully operating AI-powered business.
1
Choose Your Plan
Pick the tier that fits where your business is today — Venture, Executive, or Enterprise. Setup is handled for you.
2
Winston Gets to Work
Your AI operator activates immediately — running outbound sales, AI marketing, content, and strategy from day one. No hiring. No managing.
3
You Scale, Winston Operates
As revenue grows, Winston scales with you. Add modules, upgrade tiers, or let Winston run autonomously while you focus on growth.
Pricing
Choose your stage
Start on pricing, compare activation against monthly service, and move into the tier that matches your business today.
Lean Launch
Winston Venture
Founders replacing their first hires with one operating layer.
Activation$2,500 activation
Monthly$350/mo
Launch paceGo live in 7-10 business days
- Outbound sales engine
- Meta ads + AI content
- Executive Hub + reporting
Most Popular
Growth Stage
Winston Executive
Operators who need more volume, more channels, and faster support.
Activation$5,000 activation
Monthly$999/mo
Launch paceGo live in 10-14 business days
- Everything in Venture
- AI calling + follow-up
- Broader channel coverage
White-Glove
Winston Enterprise
Established teams handing Winston a larger revenue and ops machine.
Activation$10,000 activation
Monthly$1,800/mo
Launch paceGo live in 14-21 business days
- Unlimited agents + calling
- CRM + ad channel ownership
- Dedicated success support
First-month pricing combines activation and the first operating month. Monthly subscription renews after activation. 60-day cancellation notice required.
24 / 7
Operating without rest
6+
Business modules in one platform
0
Employees required to launch
See it in action
Watch Winston in Action
Your AI CEO — handling calls, closing deals, and running operations around the clock.
0:00 / 0:00
One platform
Everything your business needs, orchestrated by Winston
Not a stack of disconnected tools. One AI CEO running every department so you can operate from a single command.
AI Sales
Outbound & Inbound Calls
Winston qualifies leads, executes outbound prospecting, and manages inbound inquiries — converting interest into revenue without a sales team. Every call handled with executive precision.
- Live outbound calling
- Inbound call handling
- Lead qualification & scoring
- CRM updates, automatically
AI Marketing
Campaigns & Content
Full-stack marketing execution — campaigns, copy, social content, and outreach — generated and shipped without a marketing hire.
AI Trading
Powered by Investiquant AI
Investiquant AI-powered algorithmic trading for your corporate treasury — available exclusively on Winston Enterprise. Requires a minimum $60,000 Stripe balance to activate.
Dynasty Trusts
Wealth Preservation
Multi-generational trust structures and wealth preservation strategy — the legal scaffolding that protects what you build.
Incorporation Setup
Entity Formation
From entity selection to compliance, Winston walks you through each step so your business is properly structured from day one.
Executive Hub
Command & Control
Your private command center. Winston surfaces decisions, reports on every department, and executes — one screen, the whole company.
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.
AI sales and marketing
Incorporation setup
Executive Hub and reporting
Client portal access
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.
Before you activate
Three clear answers before checkout.
What happens after I purchase activation?
Winston begins the onboarding and launch work for your selected plan, including the configured workflows and platform access that apply to that tier.
Is Winston a dashboard or an operator?
The Executive Hub gives you visibility, but Winston is built as an AI CEO and operator for sales, marketing, and operating workflows—not just a dashboard to watch.
Ready to begin
Your AI CEO is ready when you are
Hand the operations to Winston and focus on the vision. Build, launch, and run your business with one elegant platform.