Memo: Shopify’s ‘Cool Kid’ Paradox

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An open letter to all eCommerce merchants. In a recent chat with 2PM Executive Member Damian Soong, the DTC founder replied with a poignant thought:

Someone needed to say that DTC isn’t Shopify.

Paul do Forno, the Managing Director of Deloitte’s Commerce Practice, chimed in with the data to support Soong’s thought, adding:

If you plotted by total platform revenue: HCL Commerce, Oracle, SAP, SalesForce would be towards the top.

Shopify has made the industry more interesting, accessible, and newsworthy. But it is not the only participant in this burgeoning ecosystem: Magento (now Adobe), Demandware (now Salesforce), SAP, BigCommerce, Squarespace, BigCartel, WooCommerce, Webflow, Square, and Wix have played pivotal roles in the development of either enterprise or merchant-level markets. Shopify is neither the biggest platform with respect to merchant volume or gross merchandise value (GMV). It sits squarely at the center of the two extremes. Yet somehow, it became the de facto operator of the DTC era.

To understand the direction of eCommerce, you must understand its past and present. During what was likely the most pivotal year in my early eCommerce career, I studied Magento from the perspective of an eCommerce brand that employed 100 or so. That earlier version of Magento was a complicated platform to understand. Its management required the employment of a dozen engineers and an equal magnitude of talent in user experience and front-end design. When I soon had my own opportunity to build an eCommerce brand alongside Kevin Lavelle, we went not to Magento, but to Shopify. We didn’t have the money to hire technical talent, nor did we have the patience to manage it on top of the challenges that we faced in manufacturing and early customer acquisition. But it’s important to recognize that this decision was made nine years ago – a lifetime in technology.

That same company of 100 is now over 1,000 strong. In under one decade, a small industry competitor became a global manufacturing leader all through direct-to-consumer channels. And they’ve done so on Adobe’s Magento. If any SaaS platform has the right to claim the dawn of the DTC era (2008), Magento could easily make that argument. Instead, it gets lost in the conversation.

Standing in a hallway of Shopify Plus’ most recent New York City conference in 2019, I sat with Shopify CEO Tobi Lutke, one of the industry’s most admired executives. I remember marveling at the production of the event. The friends, the networking, the branding of the space all communicated Shopify’s place in the eCommerce ecosystem. I applauded the entrepreneurs who shared their stories on stage with highly produced short films. Also notable was the accessibility of the C-suite executives who, frankly, should no longer be that accessible. This availability is a part of Shopify’s secret sauce. You won’t find another retail CEO of his caliber who is willing to respond to customers on platforms like Twitter and Instagram.

What I remember most about that particular meeting is the intensity of Lutke’s product focus. Suggest an idea that is outside of Shopify’s product pipeline and he will explain why Shopify isn’t right for it. He rarely waivers on his vision for what Shopify and Shopify Plus are to the eCommerce industry, or the functions that they are willing to build.

It’s this same galvanizing vision that rallies Lutke’s base of thousands of platform evangelists. Shopify’s ability to amplify its message through its partnership ecosystem has done wonders in furthering its narrative of perceived inevitability. In Shopify Unite and Network Effects [1], I wrote:

If you were to sit in a room with BigCommerce or Adobe’s c-suite and explain that product differentiation can be more than a software iteration, you won’t be sitting there for long. And that is part of Shopify’s mounting advantage. It’s unclear whether or not the original intent of the Shopify Partner ecosystem was to be a catalyst for network effects. But that’s certainly the case.

Founder Tobi Lutke, Harley Finkelstein, and team stumbled upon a new form of competitive advantage in commerce SaaS. Here, at the intersection of influence and efficacy, sociological advantages of retail brands have interfaced with an ecosystem of software as a service.

Shopify’s primary arguments for the attention it gets are valid. Its holistic approach to fulfillment, returns, and no/low code architecture will become fixtures in North America’s market as eCommerce’s percentage of retail continues to inch above and beyond 20% or 25% or 30%. And consider Squarespace or WooCommerce’s volume and Magento’s GMV: Shopify’s ability to capture mindshare despite these other companies’ advantages are as much the fault of the competitors who haven’t valued the marketing and branding aspects of business.

By weaponizing network effects, Shopify has become the proverbial cool kid of SaaS. Its brand voice is the life of the party and the center of many public discussions. There is market value in this positioning. Like Amazon, Shopify’s fortune is tied to eCommerce’s continued growth in North America. Public investors reward Shopify simply for being tied to the movement towards direct-to-consumer. It’s deserved.

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The Traditional, The Cool, The Quirky, and The Hustlers

It is important to note that this is not winner-takes-all, and what Shopify does next matters. There are eCommerce founders building on custom sites that have accomplished profitable growth. There are leaders who’ve chosen Salesforce or BigCommerce to fit their technological or philosophical needs. And in the process, they’ve built companies spewing $10s of millions in monthly EBITDA. Of course, there are examples of these feats on Shopify, but that’s the point. The democratization of eCommerce doesn’t only refer to platform simplicity.

Shopify’s ecosystem stands to benefit greatly by expanding the definition and character of the DTC industry to reach out and include the brands, founders, agencies, and technologies enabled to support them on other platforms. Some of the best and brightest stories, people, and brands are building outside of the spotlight.

The cool kids often earn the lion’s share of attention. But some of the most notable progress happens where the cool kids aren’t. That’s the paradox.

By emphasizing stories and anecdotes from founders who’ve eschewed the industry spotlight or brands that have managed growth differently than is commonly advertised, we’re closing the knowledge gap. Perhaps there was a brand founder who chose to use WooCommerce to scale and now has insights that could help Shopify-based brand founders accomplish the same. Or perhaps a Shopify Plus founder who’s successfully captured five years of year-over-year growth could explain a key strategy to a brand owner who’s built on Magento 2.3.4.

As eCommerce grows beyond 25% or 30% of American retail, we will see more examples of brands and retailers achieving a growth velocity that would have previously seemed unimaginable. In some cases, these brands will not be built with one’s preferred technical architecture. But the credibility or inclusion of these founder perspectives shouldn’t hinge on their platform preference.

Shopify Inc.’s job is two-fold. Their sales team works on converting potential users into new merchants. Their partnership ecosystem plays an essential role in replatforming existing merchants to Shopify or Shopify Plus. There are limits to this, but Shopify’s pronged ecosystem that pulls in new users and levels up existing ones is an advantage in the market, and it has an unparalleled opportunity. Where it reaches from here will determine its next phase of growth.

But they’re on notice. For every great success narrative that you hear from a Shopify partner, there five stories on competitive platforms. The DTC industry isn’t Shopify, it’s bigger than its technology or its ecosystem. This means that there is a greater opportunity to learn from, endorse, encourage, or evangelize the great work of builders who chose a different approach to a positive outcome.

By Web Smith | Editor: Hilary Milnes | Art: Andrew Haynes | About 2PM

No. 306: Platforms and Halo Effects

The commerce platform report. The term “halo effect” was first coined by a psychologist in 1920. Edward Thorndike used the moniker to describe the methods that military officers used to assess the performance of their soldiers. These assessments often revealed little variance across the categories of performance. Either the soldiers were good or bad; few performance evaluations noted “good” performance in one respect and “bad” performance in another. It is said that the halo effect is influenced most by a person’s first impression. If we see them as bad, they can do no good. If we see them as good, they can do no ill. Today, this phrase is most-often applied to brands and their equity.


The halo effect is a type of immediate judgment discrepancy. It is the tendency for an impression that is created in one category to influence the opinions of impressions created in another category.


Shopify is seemingly everywhere. In December, Digiday’s Hilary Milnes reported that Shopify’s ecosystem of 20,000 partner developers generated $800 million in agency business in 2017. It’s estimated that Shopify’s partners (several of whom are mentioned here) will earn north of $2 billion in revenue in 2019.

To build a Shopify-like eCommerce platform is not hard to do. What’s very hard to do is replicate the partnership ecosystem and the value they drive. It’s their moat. It’s not the software — their competitive advantage is the partnerships.

Jay Myers, VP of Growth at Bold Commerce

The halo effect of Shopify’s ecosystem will not be easily combated. With many of the partners becoming standout B2B brands themselves, Shopify’s group of independent eCommerce agencies serves many functions: recruiting, evangelizing, and perhaps a bit of espionage – often relaying word of advancements and initiatives proffered by competing platforms. This brand halo effect is amplified thanks to the era of the direct to consumer (DTC) brand.

2019: top commerce providers that DTC brands are looking to for partnership | Source: Cloudways

The brand appeal and staff architecture of this cohort of internet-first companies are keys to understanding why so many challenger brands instinctively select Shopify. Though not a Shopify Partner, Gin Lane’s “work” page notes the many digitally native brands that they’ve steered to the platform. These names include: Harry’s, hims, hers, Sunday Goods, Ayr, Stadium Goods, Rockets of Awesome, Cadre, Recess, alma, Smile Direct, Dia & Co, Warby Parker, Everlane, Quip, Shinola, Bonobos, and Shake Shack. Similarly, Red Antler’s “work” page boasts partnerships with Burrow, Casper, Allbirds, Brandless, Crooked Media, Snowe, and Boxed. These brands, which skew mightily towards Shopify and Shopify Plus, serve as media darlings and public relations fuel.

Tobi Lütke on Twitter

I usually don’t highlight financial milestones here, but this one is worth mentioning: As Shopify passes the $1 billion-dollar revenue mark it does so with the highest growth rate of any SAAS company ever. 🎉

In this way, Shopify’s halo effect extends beyond the agencies with whom they partner. The challenger brands, themselves, become recruiting vehicles for like-minded companies looking to build brands from zero to one. As such, newer companies like Great Jones follow the same branding methods and staff architecture guidelines

On DTC Brand Architecture

It’s common for digitally native brands (DNVBs) to go to market with over $3 million raised. This pre-revenue war chest affords companies an early branding and public relations prowess that almost guarantees seven figures of revenue in the first year.

Partnering with a Red Antler or a Gin Lane can cost a brand up to $400,000. There are often added developmental costs that these challenger brands will have to incur. In addition to the cost for the brand standards, messaging, and the essence of the brand, the right PR contact can cost a young company another $180,000 to $240,000 per year.


No. 297 The DTC Industrial Complex:

There is an entire eCommerce branding industry that fosters the ideation, launch, and early growth of direct to consumer (DtC) brands. When you notice a new digitally vertical native brand in 2018, there’s a platform aura around many of them. First you’ll notice the early PR sensationalism that they can only garner if they graduate from the right school or leave the right corporation. Then, the founders must live in the right city, have the right investors, and pay the right $25,000 per month public relations retainer.


The challenger brand CEO is very well-educated and, at this stage, CEOs tend to start the brands post-business school. Founding teams tend to begin with some combination of a product developer, finance lead, and a customer acquisition lead. Software engineering is an afterthought for many of these young product companies; this competency is often outsourced to a partnering agency. Universally, the priority for challenger brands is two-pronged: (1) making a great product (2) find an efficient way to sell said products. This often reduces the urgency to partner with technical founders or hire early, technical employees. Whereas F = founder, B = early branding, and P = early product development:

F(marketing) + F(finance) + B(outsourced) + P(outsourced) = DTC founding architecture

Shopify’s ecosystem appeals to this particular architecture. The Ottawa-based company’s continued growth depends on their management’s ability to increase the percentage of challenger brands that grow into enterprise clients. And from enterprise clients to Top 1000 online retailers. Shopify’s volume-driven style of business is a mark of its commitment to small business retailers. But it’s not the only method of accelerating enterprise growth. There are several commerce platforms with notable gross merchandise volume (GMV) across their enterprise level of clients.

The Platform Landscape

From BigCommerce to Oracle and Salesforce, the DTC era of retail extends beyond the brands that are the most talked about in design, tech media, and public relations circles. Here is the data on the top nine by gross GMV. While Shopify generates the most media buzz in small business circles: Adobe, Salesforce, and Oracle are quietly leading the enterprise+ business. BigCommerce is often viewed as Shopify’s younger sibling, however their enterprise clients now generate a gross GMV of 2.5x Shopify’s enterprise clients. The following data is derived from a recent Digital Commerce 360 report (2019):

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The platform ecosystem is vast. Of the top 1000 retailers, the majority of brands are built in-house and on custom platforms. Nearly 450 retailers have outsourced their technical capabilities to these nine companies. Moving forward, we will likely see platforms like Adobe building tools and an improved halo effect to address Shopify’s key audience and vice versa. Shopify will build tools to address more of the needs of top enterprise plus clients, as well as continuing to support the needs of the DTC brands that are adopting physical retail channels.

Specializing for a particular segment of the SMB to enterprise to enterprise plus spectrum may have dire consequences for platforms in this increasingly competitive space. As Shopify has shown, there is value in building early loyalty. Shopify is counting on a number of their industry-leading number of DTC and SMB retailers moving through the funnel to enterprise services. Additionally, Shopify’s reach grows as brands transition to Shopify from Magento or custom builds. A trend that the Adobe acquisition of Magento has potentially impacted. This continued growth would begin to tip the enterprise / enterprise+ GMV scales in their favor.

Commerce platforms advertise new capabilities with the idea that the technical merits of a platform, alone, will attract new business. To this effect, many of these platforms have deprioritized brand marketing superiority and influential partnership development in favor of technical product development and traditional advertising. Whether or not the improvement of competitor platform capabilities will outlast Shopify’s hard-wired brand loyalty remains to be seen. Objectively speaking, the sheer volume and positive brand association plays in Shopify’s favor. As does their halo effect.

Read the No. 306 curation here.

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