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Loyalty Trends and DTC Referral Flywheels with Smile CEO Mike Rossi

Loyalty Trends and DTC Referral Flywheels with Smile CEO Mike Rossi

Adrian Alfieri
Adrian Alfieri
CEO, Verbatim

Mike Rossi is the co-founder and CEO of Smile.io, the loyalty programs platform running points, rewards, and referrals for nearly a decade. Their 50,000+ clients run the gauntlet from small businesses to category-defining names like Polaroid, Topps, and Inkbox.

We sat down with Mike to discuss Smile’s transition from an agency model into a lucrative eCom tool, when brands should kickstart rewards, and how to build long-lasting communities.

“Our goal is to help as many brands as possible through frictionless onboarding and a killer product. In turn, Smile can position itself as a low-cost, low-effort tool delivering repeat sales for every brand we partner with.”

Shifting Focus: Agency to eCom Tool

In the early 2010s, the Smile.io team was an agency that assisted brands and merchants running on Magento, the eCom platform by Adobe. They built Magento Extensions for clients, which were essentially various features and integrations for stores — including one for loyalty programs that could be easily installed by any merchant on the web.

The team sold this extension as a low-level product company while continuing to operate as an agency until the wave of eCom tooling and general user demand — clients’ ad spend was ramping up while retention decreased — led to a full-time shift toward Smile.io as it is now.

In terms of the transition in business model, an agency with a notable number of clients demonstrating interest in a potential product likely already possesses the necessary validation for a strong product-market fit.

After all, shifting out of an agency model means you very likely already have a user pool that wants to pay for this product, especially when compared to someone starting from scratch in terms of product validation or sales relationship building.

However, more difficulties can arise in terms of cash flow and operations. For instance, the cash flow model for an agency entails cash committed upfront for labor, while products require essentially taking a gamble by investing an amount of capital and hoping to see ROI over time.

“If you have close relationships with your clients, you’re in a much better position to know what the market wants compared to someone on the outside looking in.”

When to Optimize Reward Timelines

When asked at what point brands should begin establishing loyalty programs for customers, Mike insists it varies among categories. He described a matrix that the Smile team utilizes, with natural purchase frequency on one axis and profit margins on the other.

A product that has high profit margins and low purchase frequency — such as cars, boats, and other vehicles — is naturally illogical for any type of rewards program for repeat purchases.

However, a product with lower margins and greater purchase frequency, i.e. foods or cleaning supplies, is far more ideal for rewarding frequent purchases and thus priming for brand loyalty.

Smile, therefore, recommends loyalty programs for businesses that fall into the latter bucket — and subsequently have greater likelihoods for success with the platform. For example, repeat purchase rates after onboarding with Smile increase by 20% on average in six months.

But Mike says the structure of the Smile platform — little-to-no cost, setup, and maintenance, with low risk and high potential reward — means rewards don’t have to be restricted to mature brands, as would be the case for a more complicated or pricey loyalty program.

Early businesses receiving as few as 10+ purchases per month can begin to reward customers while receiving 100+ monthly purchases is an ideal entry point for a Smile loyalty program.

“We’ve designed Smile to be intuitive across setup and maintenance, so I’d really feel comfortable recommending it for any stage of a brand’s growth journey.”

A Tool for Scaling DTC Communities

In Mike’s opinion, many brands have grown heavy-handed in using community as a buzzword or default method for building, or perhaps forcing, brand identity and a loyal user base — without a solid product to justify it.

Instead, the Smile team considers a user community to be the final outcome of other foundational brand components done well, such as an evergreen product, organic social materials, thorough post-purchase and return experiences, and so on.

Within that user flow, rewards should convert a user who’s simply had a positive purchase into one who’s impressed enough to return.

This then helps catalyze a population of customers who are high in repeat purchase and brand enthusiasm, AKA community members.

That community can then be solidified by whatever method organically suits the brand at hand, whether that’s Instagram comment sections, in-person meetups, or pop-up shops.

“Community is wildly overused right now. If you make something cool and help facilitate folks that want to meet each other, a community will naturally form.”

The Future of the eCom Tech Stack

For early eCom brands attempting to assemble or retool their tech stacks in a time where the ecosystem feels entirely inundated with options, Mike recommends basing your degree of experimentation and iteration on the maturity, and potentially the vertical, of your company.

In his words, a young brand can and should be iterating with numerous tooling options on a consistent basis to gauge which elements click best with both your model and your customers.

The faster you can iterate, the faster you can get to your ideal, tailored tech stack.

Once a brand matures, however, the opportunity to tinker with a stack grows more expensive and can risk a customer’s user experience. In this case, Mike strongly cautions against too many tooling stack adjustments, when dollars and time could instead be directed elsewhere.

Put simply, too little iteration early on and too much iteration at a later phase can both be equally damaging to your brand’s overall health and ability to scale over time.

“A lot of brands are in need of new competitive advantages — and Skio has been particularly great at pushing out quick iterations for subscriptions. My personal confidence in their degree of innovation was definitely a reason for investing.”

Adrian Alfieri
Adrian Alfieri
CEO, Verbatim
ObviBackboneHiyaImmiMilaKitsch
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Problem

Brainstorming 100 unique, 40-second scripts is painful.

Manually matching 20 clips (from your 10,000-video library) to each shot in your 100 unique scripts is even more painful.

Creating 10 permutations of each of the 100 ads (for A/B testing) is maximum pain.

Now imagine voiceovers, captions, music, & manually uploading all 1,000 ads to Meta & TikTok on top of this.

Products for scriptwriting (ChatGPT), competitor research (Foreplay), creative storage (Recharm, Air), editing (CapCut), creative analytics (Motion), & video production (Billo) exist, but they're not built for admaking (or just built badly).

Problem
Solution

Icon solves this with the first AI Admaker.

AI Admaker helps with scriptwriting, ad research, video creation, script-to-shot matching, permutations, voiceovers, captions, music, analytics, ad auto-launching, & more.

Solution

What they're saying

Obvi
"We went from spending hours making each ad to building entire campaigns in minutes. Icon's AI helps us shape perfect creatives at incredible speed."
Ron Shah

Ron Shah

CEO, Obvi

Products

Admaker(replaces CapCut, Adobe Premiere)

Create winning ads in minutes.

Uses AI for scriptwriting (AdGPT), video creation (A-roll, B-roll, UGC), script-to-shot matching (existing & AI-generated videos), permutations, voiceovers, captions, music, & more.

Replaces CapCut ($7.99/month), Adobe Premiere ($54.99/month)

Admaker
Adspy
(replaces AdSpy, Foreplay)

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Replaces Foreplay ($49-$99/month + $20/user), AdSpy ($149/month)

Adspy
Ads Manager
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Save time with ad manager auto-upload.

Replaces Meta & TikTok Ad Managers (direct use)

Ads Manager
Creative Library
(replaces Recharm, Air)

Save time by storing, tagging, creating, & splitting videos with AI.

Videos are used as building blocks for AI-generated ads in Admaker.

Replaces Recharm ($500-3K/month), Air ($250-$2K/month)

Creative Library
Creative Analytics
(replaces Motion)

Save money with built-in creative analytics.

Replaces Motion ($1K-$10K/month)

Creative Analytics
UGC Creators
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Save time & money with AI-generated UGC.

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UGC Creators

Story

Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
CPO, Chairman, Founder at Skio (CEO 2021-2024, $10M+ ARR in 3 years, profitable).
Previously: Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends Challenger (Top 200 North America, 100M+ players globally), Y Combinator S20 (solo founder), Columbia (transfer, dropout).
Hi, I'm Kennan!
Growing up, my dream was to be a pro gamer: this felt within reach in high school once I ranked top 200 North America in League of Legends (out of 100M+ players globally).
Despite this, I needed to support myself so I went to college and started learning to code. Coding came naturally (especially with 100 hour weeks) and I was soon skipping class to work at places like Hulu and Wieden+Kennedy (ad agency). Realizing that being paid to work full-time (vs. paying to go to school) sounded quite nice, I dropped out after 1 year to join Pinterest.
After Pinterest, I started a company called Skio which does subscription management software for brands on Shopify. In just 3 years, we've partnered with 1000+ brands (Liquid I.V., Milk Bar, Polaroid, Barstool, Unilever, KraveBeauty, Boba Tea Protein), reached $10M+ ARR (+profitable), and built an amazing team of 50.
With advancements in generative AI (video specifically), I saw an opportunity to help brands bring their stories to life exponentially faster and make marketing much better (hence Icon & building the first AI Admaker).
I love learning how we can help better. Feel free to reach out any time at kennan@icon.me.
Founders Fund

Founders Fund

Icon Investor
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Founders Fund
Peter Thiel's Founders Fund is a venture capital firm. Its partners have founded and funded companies including PayPal, Palantir, SpaceX, Anduril, Flexport, Airbnb and Stripe.
Ron Shah

Ron Shah

Icon Investor
Ron Shah
Ron Shah
Ron Shah
CEO, Co-founder at Obvi, Co-host at Chew On This, Managing Partner at Gaas for SaaS.
Roman Khan

Roman Khan

Icon Investor
Roman Khan
Roman Khan
Roman Khan
Roman Khan
Roman Khan
President, Founder at Peak21, CMO at Raycon, CMO at Know Beauty, CMO, Co-founder at Linjer, CMO at Nutrition Kitchen.
Kennan Davison

Kennan Davison

CEO, Founder
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
Kennan Davison
CPO, Chairman, Founder at Skio (CEO 2021-2024, $10M+ ARR in 3 years, profitable).
Previously: Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends Challenger (Top 200 North America, 100M+ players globally), Y Combinator S20 (solo founder), Columbia (transfer, dropout).
Yunyu Lin

Yunyu Lin

Founding Board Member
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Yunyu Lin
Head of AI at Ramp.
Previously: CEO, Co-founder at Cohere (AI CX / LLMs, acquired by Ramp), Nuro, Facebook, Y Combinator S20, Duke (dropout).
Kevin Jin

Kevin Jin

Engineering
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Kevin Jin
Previously: CTO at Kalder, Compound Labs, Robinhood, Rippling, Impira, Flexport, Google, Tesla, TSM, Vanderbilt.

Why us

Track record of things that can't be faked

Icon is the best team helping brands create winning ads in minutes.

Our CEO/Founder (who is writing this, sorry for writing in 3rd person) brings experience from Skio, Pinterest, Hulu, Wieden+Kennedy (ad agency), League of Legends (Top 200 North America, 100M+ players globally), & Y Combinator S20 (solo founder).

At Skio (subscription management software for brands on Shopify), he was CEO/Founder of the company from 2021 to 2024 helping grow revenue from $0 to $10M+ ARR in 3 years (w/ 90% margins) and a team of 50 (on $8.4M raised). Skio is profitable and still growing >100% YoY.

Our tech investors include Peter Thiel's Founders Fund, Eric Nam (K-Pop), Alex Botez (Chess), Reilly Opelka (Tennis), Max Altman (Saga), Kevin Hartz (A*, Eventbrite), & execs of OpenAI, Ramp, Flexport, Cognition, & Pika.

Our D2C investors include Ron Shah & Ash Melvani (Obvi), Roman Khan, Nick Shackelford, Jimmy Kim (Sendlane), Kevin Lee (Immi), Justin Mares (Kettle & Fire), Steph Liu (Levitate), Jason Wong, as well as founders of Eight Sleep, Yotpo, Siena AI, Replo, Novel, Parker, GR0, DCL Logistics, Aftersell, Platter, Openborder, Prescient AI, Daasity, & more.

Our team has also worked with 1000+ brands like Liquid I.V., Milk Bar, Polaroid, Barstool, Unilever, Bulletproof, 100 Thieves, Vega, KOS, KITSCH, True Botanicals, mindbodygreen, Transparent Labs, GHOST, Wild One, OpenStore, The Nue Co., Immi, DRMTLGY, Boba Tea Protein, KraveBeauty, Glamnetic, Doe Lashes, Magic Mind, Remedy Organics, & Siete Foods.

Focused on building the AI Admaker

Icon is focused on building the AI Admaker vs. also juggling the underlying AI tech.

We believe our approach is fundamentally better because we're free to choose the best technology partner for a specific job.

To illustrate this, maybe one AI-video partner specializes in face closeups while another partner specializes in body movements (where face doesn't matter as much).

If we built all underlying technology in-house, it would create a fundamental conflict of interest where we can't offer a competitor's tool (that might be better) without losing revenue.

Products
Icon

Others

Admaker
(replaces CapCut, Adobe Premiere)
Create winning ads in minutes.
Replaces CapCut ($7.99/month), Adobe Premiere ($54.99/month)
check
x
Adspy
(replaces Foreplay, AdSpy)
Save time with AI-powered ad cloning.
Replaces Foreplay ($49-$99/month + $20/user), AdSpy ($149/month)
check
x
Ads Manager
(replaces Meta & TikTok Ad Managers)
Save time with ad manager auto-upload.
Replaces Meta & TikTok Ad Managers (direct use)
check
x
Creative Library
(replaces Recharm, Air)
Save time by storing, tagging, creating, & splitting videos with AI.
Replaces Recharm ($500-3K/month), Air ($250-$2K/month)
check
x
Creative Analytics
(replaces Motion)
Save money with built-in creative analytics.
Replaces Motion ($1K-$10K/month)
check
x
UGC Creators
(replaces Billo)
Save time & money with AI-generated UGC.
Replaces Billo ($99/video)
check
x

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