How to send personalized SMS messages to upsell entrepreneurship coaching clients in 2025

Planning, prepping, and finally launching a profitable entrepreneurship coaching package could take anywhere from a couple of weeks to three months.

And then comes the upsell.

The best entrepreneurship coaches know that there’s a lot of revenue to be had in the upsell. And they don’t want to just leave it to chance or slipshod planning.

Instead, they should consider leveraging SMS marketing campaigns to send personalized upsells. With a 55% open rate + 100% “view rate” and the assurance that nearly every message gets seen, SMS is the closest thing to guaranteed visibility in 2025.

In this walkthrough, you’ll discover how to send personalized SMS messages to upsell entrepreneurship coaching clients in 2025, so you can:

• Upsell your entrepreneurship coaching offers with maximum impact
• Retain those clients for long-term revenue...

...all powered by Mobile Text Alerts, the platform that makes SMS marketing simple and effective for entrepreneurship coaches.

Define your upsell goal and ideal client

Every profitable SMS campaign for entrepreneurship coaches starts with clarity. Without a specific target and goal in mind, you risk the possibility of upselling and marketing amiss — even SMS's high view rates won’t save you.

This is why the very first step in your SMS marketing strategy isn’t writing the perfect message but grounding your campaign in two fundamentals: a measurable launch goal and a vivid picture of your ideal client.

Step one: set a measurable goal.

Think about what success actually looks like for this upsell campaign. With entrepreneurship coaches, upsell goals would usually fall into one of three categories:

1. Acquire referral clients (e.g., “enroll 30 clients in my 6-week group program”)
2. Generate revenue (e.g., “earn $15,000 in entrepreneurship coaching revenue from this upsell”)
3. Improve client retention (e.g., “increase client conversion from 2% to 5%”)

Keep your goal SMART: Specific, Measurable, Attainable, Relevant, and Time-bound. A statement like…

“Enroll 30 new high-ticket referral entrepreneurship coaching clients within 14 days of my entrepreneurship coaching upsell via SMS campaign.”

…is clear, trackable, and connected to your bottom line.

Step two: define your ideal client avatar.

Currently, the coaching industry is valued at $5.34 billion and is projected to reach $10.1 billion by 2032 according to Luisa Zhou, which means there’s plenty of demand for coaches. But not every prospect is your prospect. Knowing who you’re targeting ensures your SMS upsell campaign copy resonates and your personalized list segmentation pays off.

Your avatar should include:

1. Pain points: What problem are they desperate to solve?
2. Purchasing power: Can they afford your offer at scale?
3. Preferred communication channel: Do they respond better to fast SMS nudges or long-form email?

Here’s an example:

“My ideal client is a 35-year-old professional earning $80k+, struggling with career direction, and eager for fast, actionable entrepreneurship coaching services.”

With these two steps in place, you avoid the fatal possibility of creating, launching and marketing amiss as you create an SMS campaign for the upsell of your entrepreneurship coaching packages.

Build a compliant, high-quality SMS list

Your SMS campaign is only as strong as the list behind it. Coaches who skip compliance or settle for low-quality subscribers end up with two outcomes: wasted money and a damaged reputation. Even with the best created entrepreneurship coaching upsell, you won’t see ROI if your list is sloppy.

So one of the most important steps of creating an SMS campaign for an entrepreneurship coaching upsell is making sure it is compliant.

WHY?

Compliance comes first

In the U.S., the Telephone Consumer Protection Act (TCPA) is non-negotiable. Ignore it, and you’re looking at fines that can dwarf the revenue from your entire launch.

And if you don’t follow the mobile carriers’ SMS regulations, they will most likely block your messages so they’ll never even get delivered.

Let’s also not forget your professionalism and client trust is at stake too. As an coach, you definitely cannot put these two at risk.

To avoid such situations, here are what you’ll need:

1) Transparent consent language: Be upfront about what people are signing up for — “3–4 texts per week with launch updates and entrepreneurship coaching tips.”

2) Easy opt-out: Clients should know exactly how to opt out. (They’ll feel safer knowing they can leave anytime.)

3) Brand registration form: Registering your brand with the mobile carriers by filling out a brand registration form allows mobile carriers to pre-vet your traffic so that they know it’s legitimate.

Mobile Text Alerts handles all of this with built-in compliance features. You don’t have to worry about remembering TCPA fine print; the platform handles opt-ins, opt-outs, and record-keeping for you, and walks you through the essential (yet quite painless) brand registration process.

Give prospects a reason to join

Compliance keeps you safe. Incentives get people excited. And good news: 91% of consumers have either signed up for SMS or are open to it. You just need to tip them over the edge.

For business mentors, list-builders could include:

• A free worksheet or PDF playbook (“7 steps to career clarity for WFH moms”)
• A free 15-minute entrepreneurship coaching call
• A members-only discount code
• Early access to your next entrepreneurship coaching cohort

Keep your landing page simple: a sharp headline that explains the benefit, a phone number field, a tease of value, testimonials, and a checkbox for consent. Once they join, send a short confirmation text that sets expectations:

“Thanks for joining! Expect 2–3 texts per week with entrepreneurship coaching tips and program updates. Reply STOP to unsubscribe.”

Segment from the start

Start tagging subscribers by interest the moment they join.

Or better still, use Mobile Text Alerts to segment subscribers automatically and send laser-focused messages — like offering a discount on your entrepreneurship coaching program only to those who’ve shown interest in leadership content.

A screenshot of Mobile Text Alerts dashboard

This is the difference between a list that merely exists and a list that converts.

Choose the right SMS platform for entrepreneurship coaching upsells

Choosing the right SMS platform is key as you consider creating an SMS campaign for an entrepreneurship coaching upsell.

The right tool should make SMS list building easy, keep you safe with TCPA and mobile carrier compliance for SMS, and help you maximize SMS ROI for coaches through automations, integrations, and analytics.

It should be simple enough for your first entrepreneurship coaching SMS campaign, but powerful enough to grow with you as your list expands and your revenue climbs.

Here’s a comparison of leading platforms:

Why the features matters for your launch ROI

At the end of the day, the reliability of your entire SMS list building and launch funnel depends on your tool of choice.

With Mobile Text Alerts, entrepreneurship coaches can see higher SMS ROI because they’re not wasting time wrestling with setup, compliance, or clunky integrations.

That means you can spend less time playing “tech support” and more time sending the kind of SMS campaigns that actually convert and retain clients.

You can see for yourself for free here.

Create a high-converting launch message series

Once your SMS list is in place, next on the list is to design the heartbeat of your campaign for your new entrepreneurship coaching upsell: the message sequence. An entrepreneurship coaching upsell SMS campaign is about leading your audience through a journey from awareness to enrollment.

It’s like coaching itself: each session should nudge your client one step closer to their desired goal.

A good framework to use is the TVLL framework. A teaser, value proposition, limited time offer, last chance reminder series.

In action, these would look like:

Teaser

Goal: Build anticipation.

Example: “Big news coming this week — if you’ve been waiting for clarity in your career, this is for you.”

Tone: short, mysterious, slightly playful.

Value proposition

Goal: Highlight the benefit of joining.

Example: “Ready to get unstuck? My 6-week entrepreneurship coaching follow-up program opens Friday. Practical tools, real accountability, and work opportunities 🚀.”

Limited-time offer

Goal: Create urgency with a clear incentive.

Example: “Post-enrollment now open! First 10 clients get a free 1:1 call. Claim your spot today 👉 [link].”

Last-chance reminder

Goal: Push fence-sitters to act.

Example: “Final hours! Enrollment closes tonight at midnight. Text me back ‘JOIN’ and secure your seat.”

💡 FYI: According to one survey, 96% of respondents said they read text messages within 1 hour of receiving them, so copy and timing matters. Also, the best windows for weekdays are 9am-5pm. (47% of respondents preferred business hours.)

Launch, track, and optimize your campaign

Your SMS campaign, just like being an entrepreneurship coach, is iterative — you launch, you measure, you refine. If you want to prove SMS ROI for entrepreneurship coaching upsells, here are some examples of goals you could consider shooting for:

A sample campaign tracker.

To optimize, you need to:

• A/B test variables: try different send times, CTA wording, and incentive types.
• Watch unsubscribes: if >2%, you’re over-texting or missing value.
• Leverage AI refinements: Mobile Text Alerts can suggest stronger CTAs or subject lines based on performance.
• Segment by engagement: keep high-engagers in one bucket, nurture low-engagers with softer touches.

As you think about how to create an SMS campaign for an entrepreneurship coaching upsell, the good news is with Mobile Text Alerts, you don’t have to manually pull report for evaluation every time. The KPIs are all there in the analytics dashboard ready for you to evaluate after every campaign automatically.

How to Send Personalized SMS Messages to Upsell Entrepreneurship Coaching Clients: Summary

To review, here are the different aspects of how to send an SMS campaign to upsell an entrepreneurship coaching package:

1. Define your sales goal and ideal client
2. Build a compliant, high-quality SMS list
3. Choose the right SMS platform for upselling entrepreneurship coaching packages
4. Create a high-converting message series
5. Launch, track, and optimize your campaign

Get a free 14-day trial of Mobile Text Alerts now if you’re an entrepreneurship coach who wants a dependable business texting service that just works, without the manual hassle.

FAQ

These are the questions entrepreneurship coaches might ask when planning an entrepreneurship coaching upsell SMS campaign.

1. What if I don’t get enough opt-ins for my upsell?

Offer a stronger incentive (like a bonus session or workbook) and promote your opt-in across multiple channels (social, email, webinars).

2. How often should I text prospects for the upsell?

Aim for 3–4 messages spaced 24–48 hours apart. This balances urgency with respect for preferences.

3. Which legal steps do I need for TCPA compliance?

Only text people who have opted in, let people know they can text STOP to unsubscribe, and keep records of consent timestamp.

4. How do I measure the ROI of my SMS upsell campaign?

Divide net profit generated from SMS-driven sales by your total SMS campaign cost (credits, platform fees, copywriting time).

5. What’s the best time of day to send launch-related texts?

Weekdays between 9 a.m. and 5 p.m. — in one survey, 47% of consumers preferred business-hour texts.

6. Can AI generate my launch copy and save me time?

Yes. Platforms like Mobile Text Alerts now include AI-powered tools to draft headlines, CTAs, and timing suggestions taking hours off your prep.