CMO and Co-Founder at Obvi

Ashvin Melwani

Mike Rossi

As the Co-Founder and CEO of Smile.io, I've spent nearly a decade helping 100K+ eCommerce brands turn everyday shoppers into forever fans through customized loyalty programs, without the overhead and complexity of legacy systems.

Smile makes loyalty programs ridiculously easy to build and keeps customers coming back.

My background is in physics and software engineering, so I’ve always been passionate about solving complex problems with creative solutions

When I first entered the world of eCommerce, I started an agency. My advice to any founder now? If you want to learn fast, do consulting or start an agency. This helps you learn about real-world problems that your customers might face, but that they also want to pay you to solve.

Helping merchants 1:1 set the tone for Smile today. And since launching, over 100K+ brands have trusted our platform to run loyalty programs that turn first-time shoppers into forever customers.

I share insights on:

➝ Building customer loyalty 
➝ Discounting strategy within retail & CPG
➝ Growth strategies that focus on sustainable retention
➝ Key lessons from scaling Smile.io into a trusted platform for millions of users
➝ My journey as a founder and the challenges of scaling a startup

If these topics sound interesting to you, let’s connect!

Co-Founder & CEO

Being a flight instructor prepared me to be a CEO.
 
I learned to fly at 16 and became a gliding instructor at 18. As it turns out, teaching someone to fly teaches you how people actually learn.
 
In order to truly learn something, people have to actually be able to try it for themselves and make mistakes.
 
When you're sitting next to someone in a cockpit, you're constantly facing unique situations. So you have no choice but to build competence by making mistakes in controlled environments and learning to self-correct.
 
In flying, there are 5 levels of competency:
 
Level 1: Making dangerous mistakes without awareness
Level 2: Making dangerous mistakes but recognizing them
Level 3: Making mistakes but correcting with assistance
Level 4: Making mistakes and self-correcting
Level 5: Making no mistakes
 
The breakthrough happens between levels 3 and 4. That's when someone stops needing you to point out the problem and starts catching it themselves.
 
This same principle applies to building fast-growing teams.
 
At Smile.io, we serve tens of thousands of merchants. When mistakes happen, they can impact those thousands of merchants. So we make sure to mitigate those massive mistakes by letting people make some mistakes in lower-stakes situations.
 
By making that mistake and correcting it themselves, then they're much more confident going forward.
 
Early on we made an infrastructure mistake that impacted points rewarding times for merchants. We could've just fixed it quietly and moved on.
 
Instead, we built a retro process where we ask ourselves: if we had perfect information, if we went back in time and reproduced the situation, how could we have avoided it in the future?
 
At Smile, we've doubled our size many times. And with that comes a lot of growing pains.
 
The real skill is knowing when to let someone make a mistake and when to step in.
 
That's what I learned in the cockpit. And it's what's helped us scale Smile while staying trusted by some of the largest brands on Shopify.

Founder & CEO of Smile.io | World's Most Trusted Loyalty Platform

Starbucks announced its new rewards program this week and the internet has mixed feelings.
 
Here's my breakdown and what I'm paying attention to as the CEO of a loyalty company.
 
The program made 3 smart changes I admire:
 
1) The birthday window changes as you move up in the loyalty tiers. Green members get a reward on their birthday, Gold members get a week-long period, and Reserve members have 30 days.
 
2) Stars don't expire for Gold or Reserve members. Expiring points often alienate customers, so having higher tier loyalists get to keep their points forever feels like a win for Starbucks.
 
3) The Double Star Days update rewards the right behavior. Gold members get 4 extra stars and Reserve members get 6. The higher you go, the more valuable it becomes.
 
However, there were a couple of updates I didn't love:
 
1) The earn rate is quite low. Gren earns 1 star per $1. And Reserve earns 1.7. That's less than a 200% difference for a customer who needs to spend $2,500 to get there. If I'm a Reserve member, I'm not sure I'd feel a difference in my wallet.
 
2) Green stars do expire. Unfortunately, after 6 months of no qualifying activity, Green members will lose their stars. The idea is to make sure people stay active, but I think the impact will be more alienation than loyalty-building.
 
For merchants, I wouldn't look at this program as a cookie-cutter example. Starbucks has ~50% margins on drinks and high purchase frequency, but most brands don't.
 
If I had a loyalty program, I'd be looking to emulate the escalating perks by tier, the maintained statuses, and the behavior-tied benefits, rather than spending-informed benefits.

If you're heading to Shopify Editions in July, brunch is on us.

Last year, Smile.io and Tapcart hosted a group of agency and technology partners who are building on Shopify. This year we're doing it again. Same great format, a bit bigger, and a few new things we're adding to the mix.

We'd love to have you join us for our second annual Agency Brunch at the Ace Hotel in Toronto.

🗓️ Monday, July 20
📍 Ace Hotel Toronto
🕙 9:00am - 12:30pm

Early, I know. But Editions is worth planning ahead for. RSVP here 👉 https://luma.com/pqfakgxw

Hope to see you there!

#ecommerce #shopify #editions #shopifyplus #loyalty

Open article: The Editions Agency Brunch · Luma by luma.com

I don't know a single person who's actually made a purchase inside an LLM.
And if you're running an ecom brand, that's good news.
 
What we're seeing is that discovery has moved to LLMs. Customers are doing their research in ChatGPT, comparing options, and figuring out what they want. But the consideration and purchase are still happening back on the e-commerce platform in the majority of cases.
 
I went through this myself recently, shopping for an indoor bike. I opened ChatGPT, it listed the options, gave me links, and that was it. No brand story or relationship. Just a commodity comparison. The relationship only started when I clicked through to the site.
 
That click-through is the moment that matters. It's when a customer stops being anonymous and starts becoming yours (but only if you treat it that way).
 
The merchants I'd be worried about are the ones who let that moment go to waste. Customer arrives, buys, leaves. No data captured, no relationship started.
 
That's effectively the Amazon model, and we already saw how that played out. Nike and Under Armour eventually pulled off the platform after realizing they were handing their purchase data to a competitor who could use it to build copycat products.
 
LLMs have the potential to be the same kind of trap if you're not intentional about what happens once that customer lands on your site.
 
What the forward-thinking merchants are doing is taking more control of the customer relationship from the moment someone arrives, gathering first-party data as a natural part of the purchase process.
 
For a cosmetics brand, that means knowing her favorite color, her go-to products, her birthday, her points balance, and her VIP tier. Those are the data points that make the next email feel relevant to the customer, instead of generic.
 
TLDR: The customer who finds you through a chat interface is essentially anonymous until they land on your site. What you do with that moment is the difference between a one-time transaction and a customer you'll still be talking to in years.

Only one group of customers will ever see your rewards program page: Your die-hard fans. But a lot of merchants fall into the trap of building this page for their average customer. Here's what I'd do instead to capture those high-ROI fans (after reviewing thousands of rewards pages):
 
Average customers will stick to the purchase flow:
Google search → Find your product → Check reviews on product page → add to cart → checkout
 
So they'll never see the reward page.
 
But the die-hard fans are actively scrutinizing. They see that "learn more" button and click it because they want to understand the benefits they're getting and how they'll build loyalty over time. These people have the potential to become your most valuable customers and highest repeat purchasers. They'll buy from you 3-10 times a year, not just once.
 
So your rewards page needs to speak directly to them instead of treating it as an explainer page for passive customers.
 
The inline flow (product pages, cart, checkout) is where you talk to passive customers. But that dedicated rewards page? That's where you're having a conversation with someone who's really, really interested in what it means to be a VIP with your brand.
 
If you're thinking about launching a loyalty program or improving your existing one, remember: your rewards explainer page is prime real estate for speaking to the customers who matter most.

Major news for merchants: Starting April 2nd, United Airlines is cutting miles earned by 40% for members who don't have a United credit card. If you run a loyalty program, this is your opening.
 
This is the most aggressive move by any U.S. airline to tie loyalty to card ownership rather than actual flying. And it's a smart move for United's balance sheet. Cardholders are simply worth more.
 
But when you gate loyalty behind a financial product you don't own, you're not building a relationship with your customer, you're building one with a bank.
 
And the customers who feel that most are exactly the ones most worth keeping.
 
Here's why: customers who purchase 3-5 times a year with a brand over multiple years are probably also not the type who are transient signups for different credit cards. The loyal buyer and the credit card chaser are usually different people.
 
Across the tens of thousands of loyalty programs we work with, the ones gaining share right now aren't competing on card perks, they're winning on access and belonging. Here's how:
 
1/ They keep loyalty inside the purchase flow
 
The best programs get customers in during account creation or checkout, without pulling them out of the flow they're already in. If customers have to go looking for your program, most just won't.
 
2/ They lead with benefits, not discounts
 
Free shipping, early access, birthday bonuses - these are what top-performing programs are shifting toward. Discounts train customers to wait for a sale. Benefits build a reason to come back.
 
3/ They make the program impossible to ignore
 
An invisible program is a program that doesn't perform. The merchants we see getting the most out of loyalty have it threaded through product pages, checkout, and post-purchase flows - so customers always know where they stand and what's coming next.
 
United is building a better bank relationship. That's their call. But for every brand that doesn't have a credit card to hide behind, the window to build something more direct — and more durable — is open right now.

Your brain is 10x more likely to say "yes" to a loyalty program when you're emotionally activated. BonBon - A Swedish Candy Co. knows this, so they don't ask you to join on day one.
 
They wait until you've spent an evening watching artisanal chocolates being made, tasted 10 variations of the Dubai bar, and written your name on a fresh slab of chocolate.
 
That's when they ask: "Want to keep this going? Join our loyalty program."
 
Your dopamine is flooding and you're emotionally connected. The answer is an automatic: "Hell, yeah!"
 
If you have physical touchpoints, use them to build that investment first. Then ask for the commitment.
 
If you need any help, I’m one DM away.

If you're in luxury retail and don't have a loyalty program yet, you're leaving millions on the table.
 
High-end apparel, watches, and jewelry tend to have a small, deeply loyal customer base. Their best customers aren't spreading purchases across dozens of brands - they've got a short list and they come back to it.
 
When that's your customer base, the math on loyalty looks very attractive.
 
A 10% lift in purchase frequency from the top 500 customers in luxury brings in as much revenue as a 10% lift from the top 500,000 shoppers in the rest of retail.
 
You'd think that math would make this an easy decision, but the hesitation I hear most often is what I'd call the "discount persona" concern - the worry that launching a loyalty program signals to customers that you're a brand that does promotions, and that points and rewards will undermine the image you've spent years building.
 
That concern used to be legitimate.
 
Not long ago, your real options were to skip it entirely, manage informal VIP perks manually in-house (cumbersome, inconsistent, and a genuine fraud risk), or custom-build something from scratch.
 
But that constraint doesn't really exist anymore.
 
The customizability available now means a program can match your brand so closely that customers never experience it as a "rewards program" at all.
 
You don't have to use points language or generic tiers. Just offer early access to new collections, invitations to exclusive events, and benefits that make your best customers feel like the VIPs they actually are.
 
High-end retail has always understood the relationship over the transaction. It's just never had the right tools to deliver on that at scale. That's what's changed, and it's why the most resistant category still has the most to gain.

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The Battle

Ashvin Melwani

Mike Rossi

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The Battle

Ashvin Melwani

Mike Rossi

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Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Mike Rossi's LinkedIn Performance

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