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.
Products
Choose the Winston plan or offer that fits your next move.
Pick the operating layer for your stage. Every tier shows its one-time activation fee, ongoing monthly service, and exactly which checkout opens.
View Plans
3 Core Plans
Choose Venture, Executive, or Enterprise based on operating depth.
Activation First
One-time setup is separate from the monthly service checkout.
Faster Decisions
Standalone coaching and add-ons are lower on the page if needed.
Core Plans
Pick the operating layer that matches your stage.
Each plan shows the full commitment before you click: a one-time activation fee for launch, then ongoing monthly service. The button below opens the monthly service checkout in a new tab.
STARTER
Best for
Winston Venture
For founders replacing early hires with one lean AI operating layer.
Launch sales, marketing, and core operations without building your first support team.
$350/mo
$2,500 one-time activation
Covers setup, integrations, and launch support
$2,850 activation + first month
Opens secure monthly service checkout in a new tab. The one-time $2,500 activation is a separate setup purchase.
Activation timeline
Typical activation: 7-10 business days
Best fit
Activation covers setup, integrations, and launch support.
Included from day one
Outbound AI Sequences
Automated multi-step cold email campaigns targeting your ideal clients
Meta Ad Management
AI-built Facebook/Instagram ad creative and audience targeting
AI Content Generation
Blog posts, social copy, email newsletters, and brand content at scale
View full tier breakdown
Executive Hub Access
Your command center: KPI dashboard, client management, and revenue tracking
Client Portal
Branded portal for your clients to manage their business with your AI stack
Analytics & Reporting
Real-time traffic, funnel, and conversion data
Winston AI Butler
24/7 AI assistant for strategy, tasks, and operations
MOST POPULAR
Best for
Winston Executive
For growth-stage operators who need more pipeline, more channels, and faster execution.
Add AI calling, broader channel coverage, and deeper automation to grow pipeline faster.
$999/mo
$5,000 one-time activation
Covers setup, integrations, and launch support
$5,999 activation + first month
Opens secure monthly service checkout in a new tab. The one-time $5,000 activation is a separate setup purchase.
Activation timeline
Typical activation: 10-14 business days
Best fit
Built for teams that need more volume and faster execution.
Included from day one
Outbound AI Sequences
Automated multi-step cold email campaigns targeting your ideal clients
Meta Ad Management
AI-built Facebook/Instagram ad creative and audience targeting
AI Content Generation
Blog posts, social copy, email newsletters, and brand content at scale
View full tier breakdown
Executive Hub Access
Your command center: KPI dashboard, client management, and revenue tracking
Client Portal
Branded portal for your clients to manage their business with your AI stack
Analytics & Reporting
Real-time traffic, funnel, and conversion data
Winston AI Butler
24/7 AI assistant for strategy, tasks, and operations
Everything in Winston Venture, plus:
AI Voice Calling (Bland AI)
Outbound and inbound AI phone agents that qualify leads, book appointments, and follow up — without a sales rep
Ad Creative AI (AdCreative.ai)
Data-driven ad creative generation with performance scoring before you spend a dollar
Newsletter & Audience Platform (Beehiiv)
Build, grow, and monetize a subscriber audience with Winston-managed newsletters
Priority Support
Faster response times and a dedicated onboarding call
ENTERPRISE
Best for
Winston Enterprise
For established businesses ready to hand Winston a larger revenue and operations engine.
Install the white-glove operating layer with deeper reporting and broader channel ownership.
$1,800/mo
$10,000 one-time activation
Covers setup, integrations, and launch support
$11,800 activation + first month
Opens secure monthly service checkout in a new tab. The one-time $10,000 activation is a separate setup purchase.
Activation timeline
Typical activation: 14-21 business days
Best fit
White-glove setup for businesses ready to hand Winston a bigger engine.
Included from day one
Outbound AI Sequences
Automated multi-step cold email campaigns targeting your ideal clients
Meta Ad Management
AI-built Facebook/Instagram ad creative and audience targeting
AI Content Generation
Blog posts, social copy, email newsletters, and brand content at scale
View full tier breakdown
Executive Hub Access
Your command center: KPI dashboard, client management, and revenue tracking
Client Portal
Branded portal for your clients to manage their business with your AI stack
Analytics & Reporting
Real-time traffic, funnel, and conversion data
Winston AI Butler
24/7 AI assistant for strategy, tasks, and operations
AI Voice Calling (Bland AI)
Outbound and inbound AI phone agents that qualify leads, book appointments, and follow up — without a sales rep
Ad Creative AI (AdCreative.ai)
Data-driven ad creative generation with performance scoring before you spend a dollar
Newsletter & Audience Platform (Beehiiv)
Build, grow, and monetize a subscriber audience with Winston-managed newsletters
Priority Support
Faster response times and a dedicated onboarding call
Everything in Winston Executive, plus:
Close CRM Integration
Full sales pipeline management, deal tracking, and contact intelligence synced with your AI agents
Advanced AI Calling
Higher call volume, inbound routing, and multi-agent call flows for enterprise-level operations
Full Meta + Google Ad Ownership
Winston manages both ad platforms end-to-end: creative, targeting, budget, and optimization
Monthly Strategy Report
Executive-level performance and growth report delivered each month by Winston
Client Portal (White-Label)
Fully branded client portal you can present to your own clients
Acquisition Deal Flow
AI-assisted M&A pipeline tracker: stage management, valuations, broker contacts, and deal analysis
Dynasty Trust Planning
Facilitated setup process for dynasty trust structures through our trust partner
IUL (Indexed Universal Life) Consultation
Introductory consultation on IUL as a business wealth-building vehicle
Dedicated Account Strategy
Monthly 1-on-1 strategy session with Winston AI + owner escalation path
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.
See Winston In Motion
Watch the short walkthrough, then pick your plan.
If you want extra context before checkout, this is the fastest overview.
0:00 / 0:00
Optional Add-Ons
Add extra firepower after your core plan is live.
These monthly add-ons are available once your Winston setup is underway.
$300/mo
AI SDR (AiSDR / 11x)
AI sales development rep that researches, personalizes, and sends outbound at scale
$200/mo
AI Video (HeyGen)
AI avatar video generation for sales outreach, training, and marketing content
$250/mo
SEO Content Engine
Surfer SEO + Jasper AI — fully managed SEO content strategy and publishing
$150/mo
Video Repurposing (Opus Clip)
Automatically clip long-form video into short-form social content
$150/mo
LinkedIn Personal Brand (Taplio)
AI-managed LinkedIn posting, engagement, and personal brand growth
$100/mo
Extra AI Call Minutes (+500 min)
Add 500 additional AI calling minutes to your existing plan
To add any of these to your plan, contact us at cs@thewinstonbutler.com
Alternative Starting Points
Start lighter if you are not ready for a full Winston plan.
Free Lesson
Watch a free business lesson before you buy.
Get a quick sample of the Winston point of view before committing to a plan.
Standalone Service
1-on-1 Business Coaching & Consulting
Work directly with Justin Joslin on strategy, systems, sales, positioning, or operational decisions.
$350
per 60-minute session
What you get
- 60-minute 1-on-1 video coaching session
- Pre-session intake form to focus the conversation
- Action plan delivered within 24 hours
Common topics
- Business strategy & growth planning
- Sales system design
- Operational efficiency
- Marketing and positioning
Book Coaching
We confirm coaching bookings through the contact form within 24 hours.