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Cheers to Checkout

The 10-Day Challenge to Get Your Brand

 Ready for Its Best Holiday Season Yet

🎯 Skip the Holiday Panic. Sell More with Less Stress.

Instead of scrambling in late November, rushing posts, throwing together emails, and hoping your site is ready, you’ll glide into the season calm, confident, and already prepared.


In just 10 days, we’ll tighten your social media and email marketing so every step of your customer journey works together to drive sales while you focus on pouring, packaging, and connecting with customers.

Picture This…

🍷 Your social posts are strategic, planned, and scheduled ahead of time.


📬 Your holiday and BFCM emails are written, scheduled, and ready to sell.


🥂 You’re enjoying events, chatting with customers, and soaking in the season without wondering “Did I post today?”


🔥 While everyone else is panicking that the holidays are already here, your marketing is running smoothly in the background.

Over 10 days, we’ll focus on your two most powerful holiday sales channels:

Week 1 — Social Media & Email Marketing

This week, we’re laying the groundwork for a holiday season that flows!! You’ll lock in your seasonal content rhythm, refresh your profile so it shines, and start posting with purpose so every scroll brings customers closer to checkout.


At the same time, we’ll fire up your email engine—activating flows, mapping a holiday cadence that actually makes sense, and sending emails people can’t help but open. By the end of Week 1, you’ll have a rhythm that feels good, a profile that does the selling for you, and an email plan that keeps your brand top of mind without eating up all your time.

Week 2 — Your Website

Your website is the powerhouse of sales — the place where curious clicks turn into real checkouts. This week, we’ll give it the glow-up it deserves.


You’ll learn how to unlock wins that boost conversions, smooth out the mobile experience, and add seasonal touches that make your site feel festive. We’ll also sharpen your CTAs so they drive action.


By the end of Week 2, you’ll walk away with a practical website audit checklist, at least one live change that makes an impact, and the confidence that your site is working just as hard as you are!

Format:

Voice Notes 3x per week: bite-sized lessons + action steps

Homework: simple, 20–30 min actions that make a big impact

Live Calls: deeper trainings & Q&A

💡 Great marketing isn’t made in a hurry…

The brands that win the holiday season aren’t the ones scrambling on Black Friday; they’re the ones that had their plan in place weeks ago.


When your social, email, and website work together, you don’t just get more visibility—you get a marketing rhythm that drives sales without eating up all your time.

🚀 Amplify Your Challenge with a 1:1 Strategy Session

Want to take what you’re learning in Cheers to Checkout and make it 100% tailored to your brand?


Add on a private 60-minute Strategy Session with our team. We’ll sit down with you to map out your holiday plan, troubleshoot the tricky spots, and turn your content, email, and website into a clear sales system that feels doable — and exciting.


You’ll leave with:

  • A personalized holiday marketing roadmap built around your goals
  • Clarity on where to focus so you’re not doing “all the things
  • Action steps that amplify your challenge work and keep momentum flowing

Choose a pricing plan

Cheers to Checkout

$47

1:1 Strategy Session with Gleam Connections

$299

🙋 Your Questions, Answered

How much time will this take?

About 20–30 minutes on lesson days, 45 minutes on live call days. Weekends off.


Do I need fancy tools?

Nope, use whatever you already have for social, email, and your site.


Will there be replays?

Yes! All live sessions will be recorded and shared.


Do I have to be a wine brand?

Not at all—this works for any drinks, gourmet, or lifestyle brand and/or educators and influencers. As long as you have an offer and/or product you're good to go!

🥂 Ready to Pour Yourself a Stress-Free Holiday Season?

Sign up today, lock in your ticket, and head into the holidays with your marketing already in motion.