Day 14: Unlikely Beginnings & Bold Outcomes: How Slack and Shopify Transformed Digital Workspaces

Welcome back to From the Unexpected to the Unstoppable – How Bold Pivots Built Business Legends!

We continue our compelling journey through the annals of corporate transformation. Today, as we present the 14th blog in our series, we focus on the iterative nature of digital innovation, where sometimes, the most groundbreaking ideas don’t emerge from grand plans, but from unexpected failures or deeply personal frustrations.

This is the story of Slack and Shopify, two companies that began in seemingly niche or failing ventures, only to pivot and become indispensable tools underpinning much of the modern digital economy. Their journeys underscore a vital principle for leaders: true innovation often arises from solving a genuine, often overlooked problem, whether it’s an internal operational bottleneck or a personal need in a specific market.

Their growth, defying and thriving within various tech and economic cycles, offers profound insights into the power of iterative product development and recognizing hidden opportunities.

Slack: The "Glitch" in the Gaming Matrix

Slack’s story is a classic example of extracting immense value from a venture that failed to meet its original goal. Stewart Butterfield and his team, who previously created Flickr, launched a multiplayer online game called Glitch in 2011. Despite its unique artistic style, the game struggled to attract a significant player base in the highly competitive post-Great Recession gaming environment and was shuttered after two years.

However, within that setback lay a breakthrough. To coordinate their dispersed development teams, Butterfield’s group built an internal communication tool that proved remarkably effective. This tool streamlined workflows, enhanced real-time discussions, and improved file sharing. Soon, they realized this internal solution had far broader potential beyond gaming.

In August 2013, Slack was launched as a standalone product—a Searchable Log of All Conversation and Knowledge. Its intuitive interface, powerful search, and integration with numerous apps quickly made it a workplace staple, revolutionizing team collaboration.

Since its launch, Slack has grown into a global leader in enterprise collaboration software. Its growth was remarkable from the start, gaining 8,000 customers within 24 hours of its 2013 launch and surpassing one million daily active users by late 2015. By 2018, it boasted over 8 million daily users, including 3 million paying customers, and by its 2019 public offering, it served more than 10 million daily users across 600,000 organizations in over 150 countries.

In June 2019, Slack went public through a direct public offering to reach a market value of $19.5 billion. Slack was acquired by Salesforce in 2021 for $27.7 billion, expanding its global reach and deepened enterprise integration, becoming a vital collaboration tool for millions worldwide. The platform continues to evolve rapidly, adapting to the needs of hybrid and remote workforces and solidifying its position as a cornerstone of modern digital communication.

The platform integrates with thousands of third-party applications, making it a central hub for digital teamwork. Butterfield left Slack in December 2022. In August 2024, Box and Slack announced an expanded partnership that introduced secure AI capabilities.

Today, Slack employs about 3,000 people and operates globally, with major offices in North America, Europe, and Asia-Pacific. It is reported that Slack has 42 million daily active users and that 77% of the Fortune 100 use it. Slack has a market share of 18% in the business communications software market.

Shopify: From Snowboards to E-commerce Dominance

Shopify’s journey is rooted in frustration with existing e-commerce platforms. In 2004, Tobias Lütke, Daniel Weinand, and Scott Lake sought to launch Snowdevil, an online snowboard shop. Frustrated by cumbersome and costly e-commerce software, Lütke, a programmer, built a custom platform to meet their needs.

Recognizing the broader market potential, they pivoted in 2006 to offer their e-commerce platform to other merchants, rebranding as Shopify. What began as a niche solution became a global powerhouse, democratizing online selling for millions of entrepreneurs, small businesses, and large enterprises. Shopify went public on May 21, 2015 raising more than $131 million.

Shopify has evolved from a internal niche e-commerce solution for snowboarders into one of the world’s premier commerce platforms, powering millions of businesses globally. Revenue grew by 26% in 2024 to $8.9 billion from merchants in 175+ countries that used Shopify to generate $292 billion in sales, a 24% increase over the prior year. 2024 also marked another impressive milestone: it surpassed $1 trillion in cumulative sales processed through it and over 875 million unique online shoppers purchased from a Shopify brand.

Shopify supports a diverse range of merchants—from small startups to large enterprises—through a comprehensive suite of services including online store creation, payment processing, shipping, and point-of-sale systems. After starting with five people in a coffee shop, today the company employs over 10,000 people worldwide and continues to expand its ecosystem, helping entrepreneurs and established brands alike thrive in a digital-first retail landscape.

Key Leadership Lessons of Slack and Shopify Turning Problems into Platforms

The parallel paths of Slack and Shopify offer rich leadership lessons applicable across industries:

• Learning from Failure (Slack): The closure of Glitch was not the end but a pivot point. Leaders must cultivate a culture where failure is data for learning, not defeat. Strategic agility involves leveraging hidden value from setbacks to pivot decisively and build new futures.

  
  

• Solving Your Own Pain (Both): Both Slack and Shopify built initial products to address pressing internal problems—communication inefficiencies and e-commerce frustrations. This firsthand empathy ensured solutions were deeply useful. Leaders should encourage teams to identify internal bottlenecks as potential seeds of innovation.

  
  

• Iterative Product Development (Slack): Slack’s rise wasn’t a one-time launch but a continuous process of refinement, driven by user feedback and real-world usage. A fluid, adaptive roadmap allows products to evolve naturally with customer needs.

  
  

• Solving a Niche Problem (Shopify): Shopify’s focused start in snowboarding e-commerce allowed mastery of a specific problem space before broadening. Deep niche expertise creates a robust foundation for scalable expansion.

  
  

• Productizing Internal Tools / Empowering Others (Shopify): Transforming an internal solution into a platform for others exemplifies strategic diversification. Leaders should ask: What unique assets can be leveraged externally to empower ecosystems and create new business lines?

The Digital Age’s Defining Pivot

Slack and Shopify embody how genuine needs—discovered through trial, error, and personal insight—can spark transformative pivots. They highlight how modern enterprises thrive by building essential digital infrastructure that enables countless businesses and individuals to flourish.

Their stories emphasize that the greatest potential lies not in clinging to original ideas but in relentlessly solving problems, learning continuously, and daring to redefine your path to empower others.

Inspiring Leadership Insights

“Failure is simply the opportunity to begin again, this time more intelligently.” ~ Henry Ford, Founder of Ford Motor Company

“The value of an idea lies in the using of it.” ~ Thomas Edison, Inventor and Businessman

“When you build a product, you’re trying to build a solution to a problem for a customer. If you’re not solving problems, you’re not building a business.” ~ Tobi Lütke, Founder and CEO of Shopify

“It is not the strongest of the species that survive, nor the most intelligent, but the one most responsive to change.” ~ Charles Darwin, Naturalist and Biologist

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