In business, we’re often at the same crossroads when it comes to digital transformation and technology. Do we invest in building a dynamic, integrated ecosystem, or do we stick with our current tools, keeping costs low but limiting our growth?
I’m a Gonzaga fan. For anyone who follows college basketball, Gonzaga’s journey from a small program in Spokane, WA, to a dominant force in college basketball is nothing short of inspirational. They’re known for an unselfish style of play, taking what the defense gives them and trusting the process. They buy into the process, leaning into discipline and strategy rather than just sheer force. But last year, as I watched them face off against UConn, something was different. They started the game with energy, but slowly, they shifted from playing to win to playing not to lose. It was subtle, but the shift was visible—missed opportunities, tentative decisions, and hesitation that gave UConn the edge.
Final score: UConn 76 – Gonzaga 63.
In business, we’re often at the same crossroads when it comes to digital transformation and technology. Do we invest in building a dynamic, integrated ecosystem, or do we stick with our current tools, keeping costs low but limiting our growth? Much like Gonzaga in that game, companies can fall into the trap of playing not to lose, using technology simply to keep up rather than truly excel.
The Five Levels of Digital Sophistication: From Basic to Dominant
The path to digital growth can be broken down into stages, each with increasing levels of sophistication and integration. Understanding where you stand and what it takes to level up can be the difference between stagnation and scaling your business effectively. Here’s a breakdown of each stage:
1. Digital Novice: Just Getting on the Court
Early-stage businesses are often limited to basic tools. This level is about getting on the court and simply showing up. These companies use entry-level, DIY tools like Squarespace, Wix, or Shopify, paired with email systems like Constant Contact or Mailchimp. With basic websites, some social media engagement, and minimal data tracking, their strategy is foundational but essential. They’re focused on establishing a digital presence, often treating technology as a basic operational expense.
Key Features: Basic website, surface-level engagement, entry-level analytics, minimal security.
Challenge: Limited data insights, automation, and integration.
2. Explorer: Building Confidence
As companies grow, they begin exploring more advanced tools. They’re still budget-conscious, but they’ve discovered value in digital marketing and invest in systems like HubSpot or a customized WordPress site. They’re starting to build social engagement on Facebook, Instagram, and LinkedIn, though often relying on general templates or simple customization options. This level is akin to a sophomore player who’s getting more confident but still lacks the resources or game plan to compete at a higher level.
Key Features: Limited CRM integration, basic social media management, rudimentary data tracking.
Challenge: Budget and time constraints for advanced customization.
3. Online Business: Taking the Game Seriously
At this level, companies are going beyond “keeping up”—they’re starting to create unique customer experiences and a cohesive brand. Think of them as varsity players—they’ve got a solid game plan but are still limited by silos in their systems. They’re investing in custom UI/UX, using tools like Google Analytics with Google Tag Manager, and adding behavior tracking with tools like Hotjar.
This stage is all about refinement and optimization. They’re starting to see the value in customer segmentation and may have automated some basic workflows, but a lot of data is still in silos.
Key Features: Cohesive online brand, custom website UI/UX, customer segmentation, and basic automation.
Challenge: Siloed data, limiting the ability to gain comprehensive insights.
4. Comprehensive Digital Customer Experience: The All-Star
Here’s where things get serious. At this level, companies are looking for a comprehensive, data-driven experience. They’re not just thinking about their website—they’re investing in CRM, marketing automation, and a Customer Data Platform (CDP). They’re tracking customer journeys, leveraging personalization, and engaging on multiple channels in real time.
This level is like an all-star player who’s playing with purpose. They’ve got tools like Salesforce or HubSpot CRM, or Pardot for automation, and a CDP for centralized data. They’re making data-driven decisions, automating processes, and offering real-time engagement with customers.
Key Features: Data-driven personalization, real-time engagement, integrated data and automation, proactive customer service.
Challenge: Complex setup and maintenance costs, requiring skilled resources.
5. Gold Standard: Playing for the Championship
Here, businesses operate at the peak of digital sophistication. They’ve invested in advanced platforms like Salesforce or Adobe Experience Cloud (and sooo many other options) that enable full data integration and AI-driven insights. This is a company that, like a championship team, has fully bought into the process and is leveraging technology to outpace competitors.
Customer journeys are mapped with predictive analytics, and all touchpoints—web, mobile, physical locations—are orchestrated for a seamless experience. They’re not just playing to win; they’re setting the standard for the rest of the industry.
Key Features: AI-driven personalization, predictive analytics, fully integrated CX platforms, omnichannel orchestration.
Challenge: High costs and complexity, requiring a commitment to continuous improvement and optimization.
Are You Playing to Win or Playing Not to Lose?
Most companies see technology as a capital expense—a necessary cost to keep the lights on. But that’s the wrong way to look at it. Technology isn’t a cost; it’s an investment in growth. When you approach your digital strategy with a mindset focused on ROI, you’re thinking like a champion.
Playing to win means making strategic technology investments that drive results. It’s about using the right tools for your stage and understanding that a sharper nail is better than a bigger hammer. With the right tech strategy, you’re not just in the game—you’re setting the pace.
This isn’t just a mindset shift; it’s a competitive advantage. Play it safe, and you’ll stay stagnant. Play to win, and you’ll find yourself driving real growth. Let your digital strategy be your path to winning big. So, where are you in the game? Are you playing to win or just playing not to lose?
Also note: This season has kicked off and Gonzaga had a convincing 30+ point win over #8 Baylor (maybe this season will get back to the Play to Win mentality).
