Live Webinar Sessions

Join Check Cherry co-founders Matt and Judd for a special Office Hours edition of Check Cherry Live. ✅🍒 🎙️

This is your chance to:

* Ask questions directly to the founders
* Get tips on selling, booking, and growing with Check Cherry
* See what’s coming next for the platform

Bring your questions, ideas, and even your challenges. They'll be there to help you get the most out of Check Cherry.

No Recording Available

Every business has its own way of closing sales. But which process is right for you? In this live session, we will explore the most common sales flows inside Check Cherry, from instant online booking to proposals and appointment-first models. You will learn the advantages and drawbacks of each, see real-world use cases, and walk away with a clear framework to match the right flow to your services.

Whether you are a mobile bartender, photo booth operator, DJ, or venue manager, this session will give you the clarity and confidence to streamline your sales process and boost conversions.

Join us live to discover how Check Cherry’s powerful tools make it effortless for clients to book you online and for you to send professional, accurate proposals in minutes.

You’ll learn how to:

✅ Set up package pricing so you can charge by time and/or guest count
✅ Create add-ons that boost profits, from signature cocktails to glassware rentals
✅ Automatically calculate travel fees based on event location
✅ Collect deposits, tips, and offer payment plans — without the hassle
✅ Send contracts and gather client details in one smooth flow
✅ Get and share feedback to make Check Cherry even better for mobile bartenders

Whether you’re just starting out or ready to scale your bartending business, this session will help you book faster, close more deals, and keep your calendar full.

Take Check Cherry with you, wherever your business goes. In this live session, we’ll walk through the powerful features of our native iOS and Android apps, designed to keep you productive and in control while on the move.

We’ll cover how to:

* Manage leads, bookings, and checklists on the go
* Send and schedule messages via SMS or email
* Assign staff from your phone
* Receive real-time push notifications so nothing slips through the cracks
* Access event details and documents anytime, anywhere

Whether you’re running a solo operation or managing a full team, this session will show you how the Check Cherry app can save time, reduce stress, and help you deliver a better experience, without being tied to your desk.

What would make Check Cherry even better for you? Join co-founders Matt and Judd for a live session where we’ll explore how feature requests shape what we build—and hear your ideas for what should come next.

No Recording Available

Summer’s here, and people are taking vacations—including you and your team. Don’t let time off or double bookings slow your business down.

In this Check Cherry webinar, you’ll learn how to manage:

✅ Packages & Add-ons – control bookings without stress
✅ Backdrops – avoid conflicts automatically
✅ Staff & Employee Time Off – block out vacation days and keep operations smooth
✅ Appointments – make scheduling easy, even during summer
✅ And more…

Stay organized, keep booking, and enjoy your summer without calendar chaos.

Join us for a live walkthrough of Check Cherry’s powerful Checklist feature: your secret weapon for staying organized and delivering flawless events. Whether you're managing photo booths, DJs, or mobile bar services, we'll show you how to create, customize, and assign checklists that ensure nothing slips through the cracks. Learn best practices, automation tips, and how to collaborate with your team using checklists that live right inside each booking.

Perfect for both new and experienced users looking to streamline operations and elevate client satisfaction.

We’re rolling out a brand-new feature that makes your proposals more flexible and client-friendly: Proposal Alternatives.

With Proposal Alternatives, you can now send a single proposal link that includes multiple package options. It’s perfect for showcasing upgrades, offering choices, or giving clients a side-by-side view of what you offer and you can do it all without sending multiple proposals.

Join Check Cherry co-founders Matt and Judd for a first look at how the feature works, smart ways to use it, and why it’s a game-changer for closing more deals.

Don’t miss it, this is the future of flexible selling with Check Cherry.

Stop guessing and start charging the right amount. In this live session, we’ll show you how Check Cherry helps you automatically offer the perfect price point based on your client’s selections and event details. From flexible package pricing to smart overrides and location-based fees, you’ll learn how to take full control of your pricing strategy.

We’ll cover:

✅ Flex Pricing: Offer quotes that scale with event size and scope
✅ Discount Codes: Create promotions that actually drive bookings
✅ Overriding Packages, Add-ons & Proposals: Make one-off exceptions without breaking your flow
✅ Hourly, Daily & Unit-Based Package Pricing: Pick the model that fits your business
✅ Add-Ons: Set quantity limits, visibility rules, and pricing variations
✅ Travel Fees & Sales Tax: Automate the un-fun stuff with precision
✅ Backdrops: Include them with specific packages or charge separately — your call

Whether you’re just getting started or ready to level up, this session will help you price with confidence and close more deals.

Tired of chasing down staff, juggling calendars, or managing everything through text messages? It’s time to streamline your workflow and keep everyone on the same page with Check Cherry’s powerful staffing tools.

In this live session, we’ll walk you through everything you need to confidently manage your team — whether you’re running a solo setup with occasional helpers or managing a full squad of photo booth attendants, DJs, bartenders, or photographers.

You’ll learn how to:

✅ Assign staff to events in just a few clicks
✅ Track team availability and time-off requests
✅ Set roles and control access for different team members
✅ Send automated notifications and updates
✅ Let your team view their assignments with the Check Cherry iOS & Android apps

Whether you’re scaling up or tightening up, this webinar will help you build a more efficient, empowered, and connected team.

Learn how to make every event a hit with the perfect playlist! In this webinar, we'll dive into Check Cherry's powerful Song List features. Join us as we walk through how to seamlessly integrate and manage song selections for your events. From allowing clients to select their favorite tracks to creating a tailored playlist, we'll show you how to make music a key part of your event experience.

Whether you’re booking weddings, corporate events, or parties, the Song List feature helps you stay organized and ensure your clients get exactly what they want. Don’t miss out on learning how to elevate your event planning with this essential tool!

Clear, timely communication is essential for booking success—and automation makes it even easier! In this webinar, we’ll show you how to leverage Check Cherry’s powerful messaging tools to streamline emails, SMS notifications, and more.

What You’ll Learn:
✅ How to set up automated emails and SMS messages to save time
✅ Best practices for confirmations, reminders, and follow-ups
✅ Using templates to maintain a professional and consistent tone
✅ Personalizing messages for better engagement and conversions
✅ Avoiding common pitfalls to ensure your messages reach clients

Whether you're new to Check Cherry or looking to refine your messaging strategy, this session will help you automate communication and improve client interactions.

Ready to take your business to the next level? Join us this Tuesday for a live webinar designed specifically for new users of Check Cherry! We’ll walk you through the essential features, show you how to streamline your booking process, and answer your questions live. Whether you're coming from another CRM or starting fresh, this session will help you hit the ground running. Don’t miss it!

Say goodbye to the hassle of scheduling! Join us for a live webinar as we introduce Appointments, the latest Check Cherry feature designed to make booking meetings, consultations, and sales calls effortless. We’ll walk you through how it works, how it integrates with your workflow, and how it can save you time. Plus, get your questions answered live and see how this feature can help you streamline your business. Don’t miss it!

Struggling to find consistent, high-quality leads for your event business? You’re not alone. Whether you’re just starting out or looking to scale, mastering lead generation is essential for keeping your calendar full and your business thriving.

Get tax-ready with our exclusive webinar for Check Cherry users! We’ll guide you through the essentials of sales tax compliance, income tax preparation, and proven strategies to simplify your financial processes. Whether you’re a seasoned business owner or just starting out, this session will provide actionable advice to help you manage taxes confidently and efficiently. Don’t miss this opportunity to set your business up for success!

Let’s wrap up 2024 together! Join us for a casual chat about all the new features and updates we rolled out this year and how they’re making life easier for Check Cherry users. We’ll also share an exciting sneak peek at what we’re cooking up for 2025. This is your chance to celebrate progress and get a first look at what’s next.

Discover how Check Cherry's latest payment plan feature can transform the way you manage payments and grow your business. In this webinar, we’ll showcase how to create flexible payment plans, provide a seamless client experience, and unlock new revenue opportunities.

Join us for a live demonstration, real-world examples, and a Q&A session to ensure you’re equipped to maximize this game-changing feature. Don’t miss out on the chance to take your business to the next level!

Join us for an in-depth look at Check Cherry's mini session feature, designed to help you book more clients in less time. We'll be unveiling our latest enhancement that allows multiple people to book the same time slot, perfect for high-demand events like Santa photos, corporate headshots, and other mini session opportunities. Learn how to streamline your scheduling process, optimize your availability, and increase your booking potential. Don’t miss this opportunity to see how you can make the most out of every session!

Simplifying payments is key to closing deals faster and enhancing customer satisfaction. In this webinar, we’ll explore the best practices for making it easy for your clients to pay, including offering multiple payment options and seamless online transactions. Plus, we’ll give you a sneak peek at Check Cherry’s new ACH feature, designed to reduce processing fees and provide a convenient bank transfer option for your clients. Learn how streamlining payments can boost your bottom line, reduce friction, and improve your overall client experience. Don’t miss this chance to master payments with Check Cherry!

Join a roundtable discussion with Check Cherry co-founders Judd Lillestrand and Matt Goatcher on mastering the art of lead management. In this webinar, we'll dive into proven strategies for generating, collecting, following up, and closing leads. Discover actionable insights to streamline your lead funnel, boost conversions, and grow your business. Audience participation is encouraged so be sure to share your experiences, ask questions, and gain practical advice on optimizing every stage of your lead process. Don't miss this chance to level up your sales game!

Join us for an insightful webinar featuring Ursula from Photobooth Marketing and the team at Check Cherry, where we delve into the critical role that high-quality images and videos play in driving online sales. Learn how to elevate your proposals and online booking experience by showcasing your services with captivating visuals that resonate with potential clients. Whether you're in the photo booth industry or any other event service, this webinar will equip you with practical tips and strategies to stand out in a crowded market and close more deals. Don't miss this opportunity to enhance your online presence and increase your bookings!

https://photoboothmarketing.com/

Are you looking to take your business operations to the next level? Join us for an exclusive webinar hosted by Check Cherry co-founders Matt Goatcher and Judd Lillestrand. We'll dive into the powerful integration between Check Cherry and Zapier. Learn how to automate your workflows, save time, and enhance your customer experience by connecting Check Cherry with the apps you use every day.

Join the co-founders of Check Cherry for an in-depth webinar on leveraging Check Cherry's powerful online booking engine to streamline your business operations. We'll cover setting up your booking system, customizing client experiences, and optimizing your workflow for maximum efficiency. Whether you're new to Check Cherry or looking to get more out of your existing setup, this session will provide valuable insights and practical tips to help you attract more clients and grow your business. Don’t miss this opportunity to enhance your booking process!

Join the co-founders of Check Cherry for a fun and insightful webinar where they'll review customer websites and offer personalized feedback. Whether you're looking to improve your design, functionality, or user experience, this session is perfect for you. Get ready for a lively discussion and actionable tips to take your website to the next level!