July 14th - 16th | Replays Included
“I’m Smart. I’m Qualified. So Why Is No One Buying?”
If You’re Tired of Posting to Crickets, Playing with AI That Sounds Like a Robot, and Wondering If You’ll Ever Be Seen — This Challenge Is For You!
We’ll Show You How to Use AI to Finally Get Seen, Sell With Confidence, and
Show Up Like a Pro — Even If You’re Starting From Scratch...
July 14–16 | 100% Free | For Coaches, Creators & Experts Who Are Done Playing Small!
“I’m Smart. I’m Qualified. So Why Is No One Buying?”
If You’re Tired of Posting to Crickets, Playing with AI That Sounds Like a Robot, and Wondering If You’ll Ever Be Seen — This Challenge Is For You!
We’ll Show You How to Use AI to Finally Get Seen, Sell With Confidence, and
Show Up Like a Pro — Even If You’re Starting From Scratch...
July 14–16 | 100% Free | For Coaches, Creators & Experts Who Are Done Playing Small!
"I've seen firsthand how Chris and Jen have helped businesses skyrocket their social media presence and lead generation using AI-powered techniques. If you're looking to stay ahead of the curve and leverage AI in your social selling efforts, they are the experts you want in your corner."
Amy Porterfield - Online Marketing Expert & New York Times Best Selling Author of ‘Two Weeks Notice’
From The Desk Of Chris & Jen
Dear Hidden Expert,
Let’s get real for a second.
You’ve done the courses. You’ve posted the carousels. You’ve dipped your toe into AI tools like ChatGPT and Claude — maybe even copied a prompt or two.
And still…
You're watching other people with half your experience get the clients, the followers, the invites, the sales.
You're overthinking your content, rewriting the same caption 10 times, and wondering what you're doing wrong.
You're tired of being the best-kept secret online.
Here’s the truth:
AI won’t fix a broken brand. But when your message is clear? AI becomes your secret weapon.
And in just 3 days, we’re going to help you build your very own AI Social Selling System — the system that turns your voice into visibility, and your content into conversions.
From The Desk Of
Chris & Jen
Dear Hidden Expert,
Let’s get real for a second.
You’ve done the courses. You’ve posted the carousels. You’ve dipped your toe into AI tools like ChatGPT and Claude — maybe even copied a prompt or two.
And still…
You're watching other people with half your experience get the clients, the followers, the invites, the sales.
You're overthinking your content, rewriting the same caption 10 times, and wondering what you're doing wrong.
You're tired of being the best-kept secret online.
Here’s the truth:
AI won’t fix a broken brand. But when your message is clear? AI becomes your secret weapon.
And in just 3 days, we’re going to help you build your very own AI Social Selling System — the system that turns your voice into visibility, and your content into conversions.
WHO IS THIS FOR
This Challenge Is Built for You If:
You’re a coach, creator, or small business owner — and you’re amazing at what you do (but nobody knows it)
You’re using AI tools but your content still sounds stiff or generic
You’re stuck in “I don’t know what to post” land
You’re secretly embarrassed by your engagement and offers that flop
You know you're meant to show up louder, bolder, and more clearly — but don’t know how
WHAT YOU’LL WALK AWAY WITH…
A magnetic message that makes people get what you do
AI prompts that actually sound like you (and sell like crazy)
A system for showing up online — without overwhelm or burnout
Momentum, clarity, and confidence that lasts way beyond Day 3
A plan for using AI to grow your business (without losing your voice)
HERE’S WHAT YOU’LL LEARN EACH DAY During challenge
DAY 1:
Finding Your Perfect Clients:
Using AI to Grow Your Business
We'll kick off Day #1 with a bang! We’ll show you how to use AI to find and attract your ideal clients.
The good stuff, the tricky parts, all of it.
We'll learn about:
Our top 3 ways to use AI to figure out who your perfect clients are & why this helps your business grow…
How to make a plan to reach out to clients using AI-written messages they'll love…
The clever trick to using AI to find and connect with the right people in businesses you want to work with…
How to write super-effective messages using AI that turn new contacts into long-term clients...
Use our special tool to identify perfect clients. Includes:
• AI-optimized questions for ideal client profiles
• Key indicators of high-value clients
• Customizable outreach templates
• AI analysis of your current client base
Streamline acquisition, boost success, and grow your business with ideal clients.
DAY 2:
Using AI to Make Your Social Media Posts Go Viral
Key Ideas and Tools
On Day #2, we'll jump right into the exciting stuff... We'll show you how to use AI to make your social media posts attract more clients and grow your business.
The good parts, the tricky bits, all of it.
We'll learn about:
Our top 3 ways to use AI to make awesome posts that lots of people will share..
How to use AI tools to figure out the best times to post so more people see your stuff...
How AI can help you make cool free stuff that gets people interested in your business...
Using AI chatbots to keep your social media active all day and night, even when you're busy with other work...
Automate your social media with:
• 30 AI-generated post ideas
• AI prompts for engaging visuals
• Content mixer for cross-platform posting
• Fill-in-the-blank viral post templates
• AI-powered hashtag finder
Set it up once, then watch your followers grow effortlessly.
DAY 3:
Using AI to Sell More:
Smart Ways to Turn Leads into Customers
On Day #3, we'll jump right into the good stuff... I'll show you how to use AI to sell more and make more money from your leads.
The good parts, the tricky bits, all of it.
We'll learn about:
Our top 3 ways to use AI to find the best leads & why this helps you sell more...
How to use AI to write amazing offers that get more people to say "yes" to your projects...
The clever trick to use AI to guess what clients want and offer it before they ask...
How to use AI to keep in touch with leads and turn them into big-paying customers...
Boost credibility and sales with:
• AI-crafted trust-building conversation starters
• AI-enhanced questions to uncover client needs
• AI sentiment analysis for sales conversations
• AI-driven authentic closing strategies
Build trust, identify opportunities, and increase conversions using AI.
Fox & Friends Host to Chris: “So You Are Are One of the Few Experts in the World On AI.”
WHAT MAKES THIS DIFFERENT
No fluff. No filler. No 90-minute motivational rants.
This is tactical, transformational, and tested on over 50,000 participants.
We’re not teaching theory.
We’re handing you the exact tools we used to turn AI into a 7-figure revenue engine — and helped our clients do the same.
Our Attendees Get Results Before The Challenge Is Even Over!
Over 50,000+ People (FROM ALL DIFFERENT INDUSTRIES) HAVE EXCELLED DURING OUR CHALLENGES
WHO’S TEACHING
CHRIS WINFIELD
A visionary entrepreneur and AI education pioneer who's revolutionizing how businesses harness cutting-edge technology. As the Founder of Understanding AI and HeyVision, and Co-Founder of Super Connector Media, Chris has empowered over 50,000 business owners to leverage AI and become "The Recognized Expert" in their fields.
His expertise has been sought by tech giants like Google, Microsoft, and Apple, as well as global brands including Disney, Virgin, and NBC Universal. A media powerhouse, Chris has been featured in over 200 outlets, from The New York Times to The Today Show, and his insights grace the pages of Forbes, TIME, and Fast Company. With his unique blend of AI knowledge and personal branding expertise, Chris is shaping the future of business in the AI era.
CHRIS WINFIELD
A visionary entrepreneur and AI education pioneer who's revolutionizing how businesses harness cutting-edge technology. As the Founder of Understanding AI and HeyVision, and Co-Founder of Super Connector Media, Chris has empowered over 50,000 business owners to leverage AI and become "The Recognized Expert" in their fields.
His expertise has been sought by tech giants like Google, Microsoft, and Apple, as well as global brands including Disney, Virgin, and NBC Universal. A media powerhouse, Chris has been featured in over 200 outlets, from The New York Times to The Today Show, and his insights grace the pages of Forbes, TIME, and Fast Company. With his unique blend of AI knowledge and personal branding expertise, Chris is shaping the future of business in the AI era.
JEN GOTTLIEB
A powerhouse entrepreneur, international speaker, bestselling author, and co-founder of the INC 5000-listed Super Connector Media. Named one of the "Top 50 Speakers in The World" by Real Leaders Magazine, Jen has shared stages with icons like Oprah and Gary Vaynerchuk, leveraging her background as a VH1 host and Broadway actress to teach business owners how to become "The Recognized Expert" in their field.
Her work, featured in Forbes, Business Insider, and Goop, has transformed countless entrepreneurs into profitable, high-profile brands, cementing her status as a leading authority in personal branding and business growth.
JEN GOTTLIEB
A powerhouse entrepreneur, international speaker, bestselling author, and co-founder of the INC 5000-listed Super Connector Media. Named one of the "Top 50 Speakers in The World" by Real Leaders Magazine, Jen has shared stages with icons like Oprah and Gary Vaynerchuk, leveraging her background as a VH1 host and Broadway actress to teach business owners how to become "The Recognized Expert" in their field.
Her work, featured in Forbes, Business Insider, and Goop, has transformed countless entrepreneurs into profitable, high-profile brands, cementing her status as a leading authority in personal branding and business growth.
Is The AISS Challenge For You?
If You're Ready to...
Leverage AI to Automate Your Social Media
Generate High-Quality Leads on Autopilot
Create Engaging Content in Minutes, Not Hours
Boost Your Social Media Engagement and Reach
Personalize Your Marketing at Scale
Stay Ahead of the AI Revolution in Social Selling
Turn Your Social Media Presence into a Sales Machine
Achieve Better Work-Life Balance Through AI Automation
THEN THIS IS FOR YOU!
How AI Revolutionized Our Business... and Can Transform Yours Too
When we first discovered AI tools like Jasper, Copy.ai, DALL-E and then ChatGPT, we knew we were onto something big. As social media and branding experts, we immediately saw the potential to transform how businesses approach social selling.
We started experimenting with AI for our own business, using it to create engaging content, define ideal client profiles, and craft personalized ad copy. The results were astounding - for every hour we spent learning AI, it felt like we got 40 hours back in productivity.
Realizing the immense value this could bring to other entrepreneurs, we pivoted our business to focus on teaching AI-powered social selling strategies. We launched our first AI Social Selling Challenge in January of 2023, and the response was overwhelming. Since then, over 50,000+ people have participated in our AI challenges, eager to harness the power of AI for their businesses.
Business Insider was so blown away by our story that they did a whole feature on us!
The impact on our bottom line has been incredible. In just the first six months, our direct revenue from AI related products and services skyrocketed to $2.7+ Million. But more importantly, we've seen our clients achieve remarkable results in our challenges:
- A mindset coach who increased her TikTok followers from 200 to 3,000 using AI-generated content
- An energy expert who generated $4,832 in revenue from 3 sales during the challenge, using AI-powered content strategies learned in real-time
- Founders of an e-commerce fashion store who used ChatGPT to optimize their website content and structure, leading to a feature article in their #1 dream media outlet, “Women's Wear Daily”
We've built an entire stack of AI tools that have transformed our business operations. From generating creative content to optimizing our sales process, AI has allowed us to scale our business exponentially while actually reducing costs.
Now, we want to share these game-changing strategies with you. Join our AI Social Selling Challenge and discover how AI can revolutionize your social media presence, automate your lead generation, and skyrocket your sales. Don't get left behind in the AI revolution - let us show you how to leverage this powerful technology to transform your business, just like we did ours.
We Love to See Our Challenge Attendees Win!
We’re Really Proud of Our Media Coverage For AI & Social!
NOT SURE IF THIS IS RIGHT FOR YOU?
Who Is The AI Social Selling Challenge Perfect For?
Entrepreneurs
Doctors
Creatives
Leaders
Consultants
Digital marketers
Lawyers
Fitness trainers
Small biz owners
Professionals
Spiritual healers
Dreamers
E-commerce sellers
Real estate investors
Accountants
Wellness professionals
Coaches
Executives
Visionaries
Real estate agents
Authors & writers
Professional Speakers
Financial Advisors
Influencers
The list of professions of people who have succeeded with our Challenges just goes on and on... Essentially, if you're ready to transform your social media strategy, boost your online presence, increase your lead generation, and grow your business using cutting-edge AI tools, then this challenge is perfect for you!
Whether you're looking to save time, increase efficiency, create more engaging content, or connect with your ideal clients more effectively, the AI Social Selling Challenge will equip you with the skills and knowledge to take your business to the next level in the digital age. 🚀
HERE’S WHAT TO EXPECT
FROM THE “AISS” CHALLENGE
BEFORE This Challenge
Struggling to consistently create engaging social media content
Spending hours on repetitive social media tasks
Feeling overwhelmed by the rapidly evolving AI landscape
Unable to effectively target and connect with ideal clients on social platforms
Frustrated by low engagement and conversion rates on social media
Pouring endless hours into social media with nothing to show for it, watching helplessly as your content falls flat and potential clients slip through your fingers, while your competitors seem to effortlessly dominate the digital landscape.
AFTER This Challenge
Effortlessly generating high-quality, AI-powered content in minutes
Automating time-consuming social media tasks, freeing up hours each week
Confidently leveraging cutting-edge AI tools to stay ahead of the competition
Using AI-driven insights to precisely target and engage ideal clients
Significantly boosting social media engagement and conversion rates
Watching in amazement as your AI-powered social media strategy effortlessly attracts a flood of ideal clients, Increases revenue, and frees you to focus on what you love - all while your optimized digital presence works tirelessly for you 24/7.
You Got Questions We Have Answers!
FREQUENTLY ASKED QUESTIONS
What exactly is the 3-Day AI Social Selling Challenge?
The 3-Day AI Social Selling Challenge is an intensive, hands-on program designed to help you leverage AI tools to revolutionize your social media marketing strategy. Over five days, you'll learn how to use AI to create engaging content, automate tasks, and dramatically increase your social media effectiveness.
How do I register for the challenge?
Registration is simple! Just click the "Join the Challenge!" button on this page below and follow the prompts. You'll receive immediate access to our challenge community and pre-challenge materials.
When does the challenge start and when does it end?
The challenge runs for 3 consecutive days. Our next cohort starts on Monday, July 14th and goes until July 16th.
What time does it start and end each day?
It begins at 2pm EST (11am PST) each day and ends at 4pm EST (1pm PST) each day.
Do I need to be tech-savvy to benefit from this challenge?
Not at all! We've designed this challenge for all skill levels. We'll guide you step-by-step through using AI tools, making it accessible even if you're not tech-savvy.
How do I get started with the challenge once I've registered?
Once registered, you'll receive a welcome email with instructions to access everything including the Private Community. There, you'll find daily challenge materials, live session links, and everything else you will need!
Will this work for my specific industry/niche?
Absolutely! The AI techniques we teach are adaptable to any industry. We'll show you how to tailor AI-generated content to your specific niche for maximum impact.
What if I don't have a large social media following?
This challenge is perfect for growing your following! We'll teach you AI-powered strategies to attract and engage your ideal audience, regardless of your current follower count.
Is this challenge suitable for beginners or advanced marketers?
Both! Beginners will gain a solid foundation in AI social selling, while advanced marketers will discover cutting-edge techniques to take their strategies to the next level.
Will I need to invest in any additional software or tools?
The core challenge can be completed with free AI tools. We'll also show you some paid tools, but these are optional and not required to benefit from the challenge.
How is this different from other AI courses?
Our challenge stands out by focusing on practical, results-driven AI social selling strategies. We offer daily live sessions, personalized feedback, and a supportive community. Unlike theoretical courses, we guide you through implementing cutting-edge AI techniques that immediately impact your social media presence and lead generation. In just 5 days, you'll not only learn about AI but revolutionize your entire approach to social selling with expert mentorship and hands-on tasks.
MORE PROOF FROM THE FRONTLINES
“I got 3 clients before the challenge
even ended.”
“I finally feel excited to post again —
not anxious.”
“I sound like ME again… and my content is actually working.”
FREE TO JOIN — NOTHING TO LOSE
👇 Here’s What You Get:
3 Days of Live Training (July 14–16)
All AI Prompts, Templates + Tools
Replays + Implementation Guide
Live Coaching + Community Support
Real Momentum. Real Results.
All FREE. No catch. No pitch-fest.
Just tools that work.
👇 Here’s What You Get:
3 Days of Live Training (July 14–16)
All AI Prompts, Templates + Tools
Replays + Implementation Guide
Live Coaching + Community Support
Real Momentum. Real Results.
All FREE. No catch. No pitch-fest. Just tools that work.
P.S. – SKIPPED TO THE BOTTOM?
HERE'S EVERYTHING YOU NEED TO KNOW IN 130 WORDS...
The 3-Day AI Social Selling Challenge is a ground-breaking virtual training, uniting entrepreneurs and marketers worldwide to revolutionize their social media strategies using cutting-edge AI tools.
Starting on July 14th, you'll gain all the knowledge, skills, and resources needed to transform your social media presence into a lead-generating powerhouse.
Led by Chris Winfield and Jen Gottlieb, a pioneering force in AI-driven marketing, this challenge has already empowered over 50,000 people to boost their online engagement and sales.
You'll learn to leverage AI for content creation, audience targeting, and automation, regardless of your tech expertise or industry.
And here's the best part... it's completely FREE!
Don't miss this opportunity to revolutionize your social selling strategy today...
WHAT
Use AI To Build Your Digital Empire in 30 Days
WHEN
Monday, July 14th -
Wednesday, July 16th
WHY
Use AI To Build Your Digital Empire in 3 Days
DISCLAIMER: We can not and do not make any guarantees about your ability to get results or earn any money with our ideas, information, tools, or strategies. What we can guarantee is your satisfaction with our training. We give you a 30-day 100% satisfaction guarantee on the products we sell, so if you are not happy for any reason with the quality of our training, just ask for your money back. You should know that all products and services by our company are for educational and informational purposes only. Nothing on this page, any of our websites, or any of our content or curriculum is a promise or guarantee of results or future earnings, and we do not offer any legal, medical, tax or other professional advice. Any financial numbers referenced here, or on any of our sites, are illustrative of concepts only and should not be considered average earnings, exact earnings, or promises for actual or future performance. Use caution and always consult your accountant, lawyer or professional advisor before acting on this or any information related to a lifestyle change or your business or finances. You alone are responsible and accountable for your decisions, actions and results in life, and by your registration here you agree not to attempt to hold us liable for your decisions, actions or results, at any time, under any circumstance.
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