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How iMessage closed 30% more deals than SMS, and what that could mean for your revenue

Client expectations

Your clients are paying you for convenience, discretion, and a premium level of service.

That's the standard for every interaction surrounding their trips.

It can be challenging delivering both premium service and speed when a new charter request comes in.

Some charter companies use automated SMS to respond instantly.

But a generic business text (especially a green bubble) can feel noticeably different from a direct personal conversation.

In a Forbes study about the mindset of high net worth consumers, 78% said personalized communication significantly impacts their purchasing decisions and was the #1 factor influencing those purchases. 1

On the other hand, some companies have an aviation advisor manually text every new inquiry.

That creates a more personal experience, but it isn't particularly efficient or scalable.

This matters because conversion rates are more than 8x higher when inbound leads are contacted within the first five minutes. 2

So ideally you want to blend the speed and consistency of automation with communication that still feels personalized and meets the clientele's standard.

Luxury real estate has caught on...

Recently, companies in luxury real estate have "figured out" or "caught onto" an interesting messaging solution that retains speed and personalization.

They have switched to using Apple iMessage to communicate with clients and leads, and they have produced some interesting results.

Luxury real estate broker Ryan Serhant said that after working with 94 billionaires, one behavior consistently stood out: texting over calling.

He said it wasn't uncommon for him to negotiate $50M to $100M+ transactions over iMessage with billionaire clients. 3

Ryan Serhant, founder and CEO of SERHANT.
Ryan Serhant, founder and CEO of SERHANT.

In 2024, luxury real estate agent Tom Brennan grew from $1.9M to $17M in annual sales volume in just one year.

In a profile about his business, iMessage was listed as his highest-ROI software of 2024. 4

iMessage was more than just a convenient messaging tool, it was a sales channel.

Tom Brennan on the Real Estate Rockstars podcast
Tom Brennan, Real Estate Rockstars podcast

More companies are switching to iMessage, and it's able to close 30% more deals than SMS 5 and generate 2 to 3x higher response rates than SMS. 5

Just to clarify, iMessage is NOT: SMS, RCS, or Apple Messages for Business.

The iMessage I'm describing is a new concept: the blue bubble.

Unlike other forms of text, Apple iMessage directly interfaces with the recipient's iPhone.

As a result, the messages can have read receipts, high quality photos, videos, voice notes, group chats, and other various capabilities.

Most importantly, when you text with someone who has an iPhone, the user's messages are in a familiar blue bubble, which signals they are talking to another iPhone user, not a business.

That's why blue bubbles create trust.

Just look here: which one of these messages would you be more likely to trust? One is clearly a business and the other seems to be a person.

SMSA business SMS asking the lead to reply Yes to opt in
iMessageAn iMessage from Matt at JetCharter offering a midsize jet
Same lead, same offer. One reads like a business, the other like a person.

Apple iMessage could also be applied to the private jet charter industry.

They're different industries, but it's the same model: expensive decisions, personal relationships, and clients whose time is valuable.

Why this could fit in private aviation

Private charter has many of the same conditions where iMessage has performed well:

high value transactions, time sensitive inquiries, clients who are often traveling or unavailable, and a sales process where personal attention matters most.

Here are some ways we could think of using iMessage's unique capabilities:

  • Read Receipts: Can see if clients have viewed a message before following up
  • Rich iMessage Cards: Send photos, specs, and quote links in an interactive message card
  • Aircraft Photo Carousels: Show detailed photos of available aircraft in one swipeable message
  • Voice Notes: Send voice messages back and forth with a client instead of typing
  • Group iMessage: Add the appropriate person to an existing or new conversation, creating a group chat
  • Post Flight Check Ins: Send a short check in message after a flight, personally following up
  • FaceTime Audio: Move from the message thread into a direct phone call style audio conversation
  • and much more...

But it doesn't have to be that complicated. For your business it could look as simple as:

New flight request → Personalized iMessage → Client responds → Aviation advisor takes over

From there, your team handles the relationship normally: discussing the itinerary, answering questions, sharing aircraft information, or moving into a call when it makes sense.

The client gets speed and convenience. Your team keeps the personal relationship.

If iMessage isn't available, the conversation can automatically fall back to RCS or SMS.

What I'm offering you

I'd welcome the opportunity to learn how your current sales process works and see whether iMessage could create a meaningful advantage.

I only want to work with a select few companies.

I'll consult for 2 weeks, review your current sales and follow-up process, assess the technology you're already using, and identify if iMessage could support your revenue.

After, I'll show you where we believe iMessage does, or doesn't, make sense for you and build you a complete opportunity assessment.

The entire assessment is free, we just want to explore what's possible.

You don't have to invest in a new system just to find out whether it could work.

We'll do the work first.

If we find a real opportunity, we'd like the chance to partner with you to implement it.

What's next?

Ready to find out whether iMessage could improve the way your team cultivates relationships?

Let's talk...

I'm Caton Summers, founder of CaptaFlow, and I would welcome a chance to discuss what's possible.

No stress or pressure, just use the button below to pick a time that's convenient for you.

I look forward to speaking with you!

Book a call

or email info@captaflow.com

Caton Summers, founder of CaptaFlow

Sources

  1. Forbes Research, Most Affluent Shoppers Want to Browse Online but Buy In-Store (2025)
  2. InsideSales, Response Time Matters (Lead Response Study 2021)
  3. Ryan Serhant on LinkedIn
  4. HousingWire, How a new agent closed $17M in year 2 using 1 simple strategy
  5. Sendblue, Send iMessages in GoHighLevel with Sendblue