
Win back past clients and earn prizes while you do it
Past clients are the highest-converting audience in your database. They already know your business, they've already paid you, and a well-timed message is often all it takes to bring them back.
The win-back automation does the outreach for you. It's pre-built, tailored to your business by ISAAC, and triggers automatically based on your client data. Most businesses see replies and bookings within 24–48 hours of turning it on.
The Win-Back Challenge is simple: activate the automation, watch clients come back, and earn entries into monthly $1,000 prize draws.
Here's how it works
Activate the pre-built win-back automation in Marketing Suite anytime before September 30. From the day you activate, you have up to 60 days to hit milestones and earn entries — or until September 30, whichever comes first. Winners are drawn at the end of each month.
Every Wednesday is Win-Back Wednesday. Post your wins on social that day and earn double entries.
Milestones
Milestone | What Happens | Entries Earned |
|---|---|---|
Activate a win-back automation | Activate a win-back automation in Marketing Suite. | 1 |
Win Back Your First Client | Win back your first client through the automation. | 5 |
Celebrate Your Wins | Share a post on social about clients returning and tag @WellnessLivingSoftware | 10 any day / 20 on Win-Back Wednesday |
Maximum entries: 26 (if your Celebrate Your Wins post goes up on a Win-Back Wednesday). Standard maximum is 16.
Milestones 1 and 2 track automatically on the WellnessLiving side. Milestone 3 is verified manually by the WellnessLiving team.
The prizes
$1,000 per month in prizes, drawn at the end of each month from May through September. Each draw has 2 winners.
Draw date | Prizes |
May 31 | 2 × $500 Visa gift card |
June 30 | 2 × $500 Visa gift card |
July 31 | 2 × $500 Visa gift card |
August 31 | 2 × $500 Visa gift card |
September 30 | 2 × $500 Visa gift card |
Entries carry over. An entry earned in May is eligible in every subsequent draw. Each winner can only win once — previous winners are not eligible for future draws.
Win-Back Wednesday
Every Wednesday, participants who post their Celebrate Your Wins content earn 20 entries instead of 10.
Post your results and tag @WellnessLivingSoftware on Instagram, Facebook, or LinkedIn. Reference a specific outcome: clients who came back, bookings made, familiar faces returning.
Win-Back Wednesday starts May 20 and runs every Wednesday through the contest period.
Use the image generator to easily create your custom post and share it on your social media!
Create my social post
Getting started
Activating the automation is your first step and your first entry.
Log in to WellnessLiving
Open Marketing Suite from the sidebar
Go to Automations
Find the pre-built Win-Back automation
Click Activate
The automation is already written by marketing professionals and tailored to your business by ISAAC. You don't need to write anything or configure anything.
See this article for more details on activating the win-back automation.

Your progress tracks itself
Both the Activate and Win Back Your First Client milestones track automatically on the WellnessLiving side. Nothing to submit.
For Celebrate Your Wins, the WellnessLiving marketing team monitors tags on Instagram, Facebook, and LinkedIn and records entries manually. Post date determines your entry count, so Win-Back Wednesday posts are verified against the date of the post.
Important dates
Date | What happens |
May 13 | Contest launches |
May 20 | First Win-Back Wednesday |
May 31 | First monthly draw |
Every Wednesday | Win-Back Wednesday: double entries on social milestone |
July 31 | Last day to activate and get the full 60-day window |
September 30 | Contest closes + final monthly draw |
Activity must occur within your qualification window to count.
Frequently asked questions
Do I need to complete all milestones to win? No. Each milestone earns entries independently. More milestones means more chances to win, but Milestone 1 alone gets you into the draw.
What's my qualification window? You get up to 60 days from the date you activate, or until September 30, whichever comes first. Activate May 15 and your window closes July 14. Activate July 31 and your window closes September 29. Activate September 1 and your window closes September 30.
Is this based on who wins back the most clients? No. Winners are drawn randomly from all eligible entries. A solo practitioner has the same odds per entry as a large gym.
Do I need to sign up or opt in? No. Any active WellnessLiving customer who activates the win-back automation during the contest period is automatically eligible.
Do I need SMS / Message Center to participate? No. The win-back automation works with email. If you have Message Center, the automation can include SMS steps for stronger results, but it's not required to enter.
How do the social entries work? Post and tag @WellnessLivingSoftware on on Instagram, Facebook, or LinkedIn. Reference a specific client outcome. The WellnessLiving team verifies and records your entry. Posts on Win-Back Wednesday (any Wednesday during the contest) earn 20 entries. Posts on any other day earn 10. Maximum 20 entries from social per participant, regardless of how many qualifying posts you share.
Can I use the Results Image Generator? Yes. Enter your results and it generates a shareable graphic you can download and post. Access it here.
If I win in May, can I win again? No. Each winner can only win once. Previous winners are not eligible for future draws.
How do I confirm eligibility? Full contest terms and eligibility requirements are in the Official Rules below.
Eligibility
To qualify to win:
Active WellnessLiving customer in good standing during the contest period
Win-back automation activated in Marketing Suite during the contest period (May 13 – September 30)
Automation active at the time of winner selection
Full contest rules available below.
MARKETING SUITE WIN-BACK CHALLENGE - OFFICIAL RULES
WHEREAS WellnessLiving Systems Inc. ("WellnessLiving") offers Marketing Suite, an integrated marketing automation platform that enables businesses to create and manage automated marketing campaigns including email, SMS, and push notification sequences; and
WHEREAS WellnessLiving wishes to conduct a promotional contest to encourage activation and meaningful use of the Marketing Suite win-back automation feature, and to recognize participating businesses that implement automated win-back campaigns within their operations;
NOW THEREFORE, WellnessLiving hereby establishes the Win-Back Challenge (the "Contest"), which shall be governed by the following Official Rules and Regulations.
1. Sponsor
The Win-Back Challenge (the "Contest") is sponsored by WellnessLiving Inc. ("WellnessLiving"), located in Ontario, Canada.
2. Eligibility
The Contest is open to active WellnessLiving customers (businesses) who:
Maintain an active WellnessLiving subscription in good standing during the Contest Period, as hereinafter defined;
Are in good standing on all accounts, services, and subscriptions with WellnessLiving (e.g., no overdue balances and no suspended account status);
Have the pre-built win-back automation activated in Marketing Suite during the Contest Period and at the time of winner selection;
Reside in Canada (excluding the Province of Quebec), the United States, the United Kingdom, or Australia (i.e., the place of business for the active account with WellnessLiving);
Have reached the age of majority in their jurisdiction of residence for sole proprietorships or are an active entity as a going concern continuing under the jurisdiction they were formed under;
Failure to maintain at any time an active WellnessLiving subscription in good standing and an activated win-back automation during the Contest Period and at the time of prize confirmation as announced by WellnessLiving will result in disqualification.
Employees, contractors, directors, officers, representatives, and their immediate family members of WellnessLiving Inc. are not eligible.
The Contest is void where prohibited.
3. Contest Period
The Contest begins on May 13, 2026 at 12:00 AM Eastern Standard Time (EST) and ends on September 30, 2026 at 11:59 PM EST (the "Contest Period").
Each participant's qualification window begins on the date they activate the pre-built win-back automation and extends for sixty (60) days from that date, or until September 30, 2026 at 11:59 PM EST, whichever occurs first. Only qualifying milestone activity completed within a participant's qualification window will be eligible for Entries.
WellnessLiving's internal system time shall be the official timekeeping system for the Contest.
4. How to Earn Entries
Participants earn entries ("Entries") by completing the following milestones during their qualification window:
Activate the pre-built win-back automation in Marketing Suite — 1 Entry
Have at least one (1) client recorded as won back through the win-back automation, as tracked by WellnessLiving's internal systems — 5 Entries. This milestone may be claimed once per participant.
Share a social media post on Instagram, Facebook, or LinkedIn celebrating client returns and tagging @WellnessLivingSoftware, as verified by WellnessLiving's marketing team — 10 Entries. Posts published on a designated Win-Back Wednesday (every Wednesday during the Contest Period, beginning May 20, 2026) earn 20 Entries instead of 10. Entries from this milestone are capped at a maximum of 20 Entries per participant regardless of the number of qualifying posts submitted.
The maximum number of Entries per participant is 26.
Social media milestone Entries are limited to qualifying posts that reference a specific outcome (clients returning, bookings, or similar results). Reposts of WellnessLiving content without original commentary do not qualify. Duplicate posts across platforms count as one qualifying post per submission.
The Activate and Win Back Your First Client milestones are tracked automatically through WellnessLiving's internal systems. Social media milestones are verified manually by WellnessLiving's marketing team.
In the event of any discrepancy regarding milestone completion or Entry totals, WellnessLiving's internal records shall be deemed final and binding.
No additional purchase is required to enter beyond maintaining an active WellnessLiving subscription, which must remain active throughout the Contest Period.
5. Prizes
Ten (10) prizes will be awarded across five (5) monthly draws:
Each monthly draw awards two (2) prizes of $500 USD Visa Gift Card each, for a total of $1,000 USD per draw.
Monthly draws are scheduled on or around the last day of each month: May 31, June 30, July 31, August 31, and September 30, 2026.
Total prize pool: $5,000 USD.
Prizes:
Are non-transferable
Cannot be exchanged for cash (except where required by law)
May not be substituted by the winner
Each participant may win a maximum of one (1) prize across all draws. Previous winners are not eligible for subsequent draws.
WellnessLiving reserves the right to substitute any prize with one of equal or greater value if the advertised prize becomes unavailable.
Prize values are stated in USD. Where applicable, prizes may be issued in local currency equivalent at the Sponsor's discretion.
Winners are solely responsible for all taxes, duties, and reporting obligations associated with prize acceptance.
6. Winner Selection
Winners for each monthly draw will be selected by random draw from all eligible Entries accumulated up to and including the last day of that month.
Entries carry over between draws. An Entry earned in May is eligible in all subsequent monthly draws, subject to the one-win-per-participant limit set out in Section 5.
Each monthly draw will take place within ten (10) business days following the scheduled draw date.
Odds of winning depend on the total number of eligible Entries in the draw pool at the time of each monthly draw.
7. Winner Notification & Claim Process
Selected entrants will be notified by email and/or phone using the contact information associated with their WellnessLiving account within ten (10) business days of each monthly draw.
To claim a prize, selected entrants must:
Confirm they maintained their active subscriptions with WellnessLiving in good standing during the Contest Period up to and including the date of winner selection
Confirm that the win-back automation remained activated in Marketing Suite at the time of winner selection
Respond within fourteen (14) business days of the day the notification is sent
Sign and return any required declaration and release documentation requested by WellnessLiving
If the win-back automation is not activated at the time of verification, the entrant will be deemed ineligible and an alternate winner may be selected.
Canadian residents selected as potential winners must correctly answer a time-limited mathematical skill-testing question without assistance to claim their prize, as and if required by Canadian law.
If a selected entrant:
Fails to respond within the required timeframe
Fails to correctly answer the skill-testing question (if applicable)
Is found ineligible
Is not in good standing at the time of winner selection
WellnessLiving may select an alternate entrant at its sole discretion.
8. Publicity Release
By accepting a prize, winners agree that WellnessLiving may use their name, business name, city, province/state, and/or likeness for promotional and marketing purposes without additional compensation, unless prohibited by law.
9. Limitation of Liability
By participating in the Contest, entrants agree to release and hold harmless WellnessLiving Inc., its affiliates, subsidiaries, officers, directors, employees, and agents from any liability, loss, damage, cost, or expense arising out of participation in the Contest or acceptance, use, or misuse of any prize.
WellnessLiving is not responsible for:
Technical malfunctions and downtime
System failures affecting Marketing Suite tracking or reporting
Incomplete or inaccurate dashboard reporting or data delivery
Lost, late, misdirected, or corrupted entries
Unauthorized intervention
Theft
10. Disqualification
WellnessLiving reserves the right to disqualify any participant who:
Tampers with the entry process
Violates these rules
Attempts to manipulate milestone tracking systems
Engages in fraudulent or abusive conduct
All decisions of WellnessLiving are final and binding.
11. Privacy
Personal information collected in connection with this Contest will be handled in accordance with WellnessLiving's Privacy Policy, save and except for when announcing and advertising the winners or other related publicity pursuant to section 8.
12. Right to Modify or Terminate
WellnessLiving reserves the right, at its sole discretion, to amend, suspend, or terminate the Contest if fraud, technical issues, regulatory changes, or other factors impair the integrity or proper functioning of the Contest or prejudice or adversely affect WellnessLiving.
13. Governing Law
The Contest is governed by the laws of Ontario, Canada, without regard to conflict of law principles.
Any disputes shall be resolved exclusively in the courts located in Toronto, Ontario, Canada.