Unpicking the puzzle: Simplifying digital transformation in Media

As Ken Segall, the former Apple creative director behind the iconic “Think Different” campaign and author of Insanely Simple, put it: "The simplest way isn’t always the easiest." His work has long championed simplicity as a competitive advantage, something media organizations must now embrace in their digital transformation efforts.

With constant pressure to monetise attention across channels, adopt new technologies, and deliver seamless digital experiences, media companies are in a race to modernize. But in the scramble to transform, many are unintentionally recreating complexity rather than removing it.

The result is overcomplicated tech stacks, legacy processes stitched together with manual workarounds, and a cultural bias toward customization because it feels like the only way to reflect unique media business models.

This article offers a practical framework for media leaders to help cut through complexity, prioritize transformation efforts, and avoid costly detours. Choosing the “simple” approach for the sake of it isn’t what we’re suggesting here. Instead, be strategic by understanding where simplification drives value, and where minimum viable product (MVP) workarounds are worth the trade-off.

The digital dilemma: Why media organizations struggle with simplification

Media businesses have never been short on innovation, but their operations often tell another story. Here are common challenges we see across the sector:

• Fragmented monetization models: Advertising, subscriptions, licensing, syndication, events, all with different billing, compliance, and customer data needs.
• Third-party overload: Partnering with platforms (e.g. Google, Meta, Apple) creates reliance on external data and revenue flows, adding layers of process and tech.
• Legacy platforms that won’t die: Old CMSs, CRMs, and billing engines still underpin mission-critical functions. Unpicking these without disrupting revenue is daunting.
• Customization creep: Transformation projects quickly spiral when teams insist on replicating every legacy nuance in new systems.
• Inflexible architecture: Some platforms look sleek but don’t support fast experimentation or agile go-to-market. And that’s a dealbreaker in media.

Transformation must simplify these realities rather than mask them with more tech.

A playbook for media simplification: Align, simplify, prioritize

There are three core principles we recommend every media implementation team adopt:

1. Be aligned 

   When a team doesn’t know what an implementation is trying to achieve, odds are it’s not going to go well. Creating clear implementation principles and themes that can be repeated by a majority of your team working on the implementation will help create clarity. Recently, we’ve seen the success that can result in simply using the word ‘simplification’. After one client’s project kick-off, the team felt comfortable challenging design ideas with questions like “is this simple enough?” or “how will that simplify things?” Another key principle that should be considered is whether the complexity will be worth it, or more simply, will the complexity provide enough value, strategically or monetarily, to cover the cost of building it into the new world? 

   A strong set of principles will enable your team to make recommendations and provide structure for pragmatic decision-making.

2. Be simple

   What is the simplest thing we can do to achieve an outcome?

   Customization can be the blight of many implementation projects. In pre-sales, SaaS providers will give assurances of out-of-the-box functionality or of seeing your specific use case before, but a single platform can rarely meet every use case without custom work. Go back to your principles and the ‘why’ of the implementation, and then ask: how can we simplify that? If, on reflection, it is still valuable and required and cannot be simplified, then you should look at how you can deliver it simply using current or incoming technologies. This can and has been implemented for macro and micro decisions. 

3. Be flexible and quick

   The media environment is a rapidly changing space, and companies find themselves in a maelstrom of challenges, be it AI overviews reducing website views, subscription legislation (namely DMCCA 24), or new monetization opportunities seemingly appearing daily. Media companies can’t afford to realize the value of transformation over time, and they can’t get stuck with inflexible architecture or suppliers that are unable to service the market at the required pace. Transformation teams should look to deliver the most valuable part of the project as quickly as possible.

Building a media-ready tech ecosystem

A single platform won’t solve everything. The modern media stack is about integration and agility rather than monolithic systems.

Consider this simplified, scalable architecture:

• Subscription and billing: Manages recurring revenue, usage-based models, and dunning
• CRM: Centralised customer view, service, and segmentation
• Data platform/BI: Tracks subscriber behavior, churn, and LTV
• ERP and finance: For revenue recognition, compliance, and reporting
• Payments: Secure, flexible collection methods (especially mobile/paywall integration)
• Identity and access management (IAM): Seamless cross-channel logins.

Each piece should plug into the next without extensive custom plumbing.

Conclusion

Digital transformation in the media industry doesn’t need to be daunting. Focus on simplification, alignment, and agility to unpick legacy systems and processes. Be clear on which outcomes matter, design around simplicity, and deliver value quickly. With the right mindset and principles in place, transformation will build a smarter, more adaptable business for the future.

Ready to simplify your digital transformation? Contact us today to build a smarter, more adaptable media business.