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The Complete Guide to Upselling Packages and Add-Ons for Event Pros

September 29, 2025 Check Cherry

Why Upselling Matters

If you’re a DJ, photo booth operator, or mobile bartender, you already know booking clients is only half the battle. The real opportunity lies in increasing the value of each booking. Upselling through packages and add-ons allows you to:

  • Boost revenue without booking more events
  • Deliver a premium client experience
  • Stand out from competitors who only offer “basic” options

With the right approach, upselling feels less like sales and more like giving your clients exactly what they want.


Master the Power of Bundles

Bundles make it easy for clients to choose a “better” package without feeling nickel-and-dimed.

  • Good → Better → Best packages help guide clients toward premium choices.
  • Example:
  • Basic DJ Package – 4 hours, sound system
  • Premium DJ Package – Add lighting, MC services
  • Elite DJ Package – Add custom playlist consultation, dance-floor lighting, photo booth discount

Pro Tip: Always anchor your pricing with a high-end package so mid-tier feels like the “smart” choice.


Strategic Add-Ons That Sell Themselves

Add-ons work best when they solve problems or add “wow” moments for clients:

  • DJs: Uplighting, ceremony sound, extra hours, dance floor effects
  • Photo Booths: Backdrops, props, guest books, instant social sharing
  • Bartenders: Signature cocktails, extra staff, glassware upgrades, late-night service

When presented clearly, these extras often feel like no-brainers.


Pricing Psychology That Works

How you present pricing matters as much as the number itself.

  • Tiered pricing: Show three options, clients usually pick the middle.
  • Decoy effect: Add a “just okay” package that makes the premium one shine.
  • Perceived value: Frame add-ons as investments in memories (“uplighting transforms your venue atmosphere”) instead of line-items.


Upselling at the Right Time

Timing is everything. The best upsell moments are:

  • During the booking flow: When excitement is highest.
  • After booking, before the event: Send automated reminders about popular add-ons.
  • At renewal/returning events: Offer loyalty discounts with premium packages.


How Software Makes Upselling Effortless

Trying to upsell over the phone or in email chains often fails. But when software automates the upsell process, clients see options naturally.

With Check Cherry, event pros can:

  • Display packages and add-ons inside the booking form
  • Let clients upgrade instantly without back-and-forth
  • Use branded invoices and proposals to showcase premium options
  • Set up automated follow-ups that suggest add-ons clients often buy

This not only drives more revenue but also makes the client feel in control of their choices.


Final Thoughts

Upselling isn’t about being pushy — it’s about helping clients create the event they truly want. By packaging smartly, offering irresistible add-ons, and leveraging tools like Check Cherry, DJs, photo booth owners, and mobile bartenders can maximize revenue while delighting clients.

Now’s the time to review your current packages, rethink your add-ons, and make sure your booking process is designed to upsell for you.

People will ❤️ how easy it is to book you online.

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