Preparing Your Business to Upgrade Sitecore – It’s More Than Just Technology

Joel Gerber
Mountain representing Sitecore upgrade
Your choice of a digital platform like Sitecore opens up many opportunities to achieve improved customer experiences (CX) through its powerful personalization, marketing automation, and access to important user data.

But just like any other digital tool, you can’t set it and forget it. Upgrades are inevitable to continue to experience – and expand – the benefits of your investment. But when exactly should you upgrade Sitecore?

How Do You Know When it’s Time to Upgrade?

Upgrading your Sitecore platform has many technical advantages, from the obvious – bug fixes and important security enhancements – to the advanced – integration capabilities, updated CX opportunities, and next-level marketing features.

You know it’s time to upgrade when:

  1. Your version lacks the latest features offered in a newer version needed for current CX expectations.
  2. Your version is nearing the end of its lifecycle, meaning improvements on your current version will no longer be made.
  3. Your purchased Extended Support is ending.

For whatever reason an upgrade is on the horizon, planning is the key to making it a successful endeavor.

What Does a Successful Upgrade Look Like?

Clients who know it’s time to upgrade may hesitate because a successful upgrade takes time, strategic management, and technical expertise. But, proper planning and the right partner helps you avoid the common horror stories associated with software upgrades including site downtime, stalled and abandoned upgrades halfway through the process, or incurring the cost of completely re-platforming.

You know a Sitecore upgrade is successful when:

  1. The upgrade solves the CX and business issues you set out to solve.
  2. You had the technical leadership and skills to complete the upgrade without over-burdening your existing development team.
  3. It launched correctly because quality assurance was maintained, and the due diligence of comprehensive testing ensured there were no errors.
  4. You are set to strategically scale because your team considered future needs and built them into your implementation.

Your Sitecore upgrade involves thinking beyond just the technical questions. As a Sitecore Partner, here are the nine questions we always ask clients to lay the groundwork for a successful upgrade.

Nine Questions to Ask (and Answer) Before You Upgrade

1) When Does Your Sitecore Version Expire?

It’s important to know your Sitecore version’s lifecycle expiration date so you can make proactive, strategic plans for your upgrade. When your Sitecore version expires you lose access to many benefits including security and software updates, access to new features, and compliance and/or compatibility with new regulations and digital tools.

Upgrading to a newer version ensures continued access to these benefits. If an immediate upgrade is not feasible, Extended Support can buy you some time with the version you have.

2) What Kind of Support Does Your Sitecore Platform Currently Have?

It’s important to understand which of the Sitecore support types you have and what it offers you.

To summarize, Sitecore has three support offerings:

  • Mainstream Support for active versions of Sitecore.
  • Extended Support for phased-out versions of Sitecore that will still be actively supported for an additional fee.
  • Sustaining Support for versions that have been phased out entirely and are no longer available for Extended Support.

If you choose Extended Support in lieu of an upgrade, upon expiration, you get moved to Sustaining Support which is very limited and excludes any security updates or fixes – opening your company up to unnecessary risks.

3) What CX or Business Problems Are You Trying to Solve?

You bought Sitecore to solve your CX and business problems. Consider this potential upgrade as an opportunity to get the most out of your Sitecore investment.

Where can this upgrade help improve your customer experience? What pain points can be solved with upgraded features and functionality? Clearly identifying the problems you want to solve will help determine which upgrade supports your business goals.

For example, a bank might use the latest Sitecore features to solve customer experience issues by introducing AI-driven chatbots for instant support, personalized financial advice based on individual customer data, and interactive financial tools that make managing finances easier and more engaging. These enhancements can significantly improve the digital banking experience and customer satisfaction.

4) How Confident Are You in Your Data?

Sitecore can do amazing things with your data to help gain and retain customers. However, you need to truthfully assess the current state of your data to determine if it is clean enough to support customer lifetime value-boosting features.

For example, high-quality data enables enhanced personalization. According to Deloitte, brands with high personalization are 48% more likely to exceed revenue goals, 71% more likely to report improved customer loyalty, and 67% more likely to report increased frequency of purchases by customers.

To use these advanced features, your data needs to be clean, consistent and reliable. If your data falls short, creating a data strategy in tandem with your Sitecore upgrade can drastically improve your CX results.

5) Should You Consider a Cloud Option or On-Premises?

Every company needs to answer this question for themselves based on their comfort level, security protocols, and existing on-premises investments. While both options are valid, it’s important to evaluate each path and work any extra steps needed into your upgrade implementation.

6) What Capacity Do You Have to Work on the Upgrade?

Proper planning and resource allocation minimize the risk of delays and ensure that upgrade tasks do not interfere with ongoing development needs, such as new customer products or tools.

A typical Sitecore upgrade can take from 6 to 10 months and requires a team with diverse skill sets including:

  • Sitecore Architect
  • Sitecore Developer
  • DevOps Engineer
  • Test Engineer
  • Sitecore Project Manager

Identify your in-house skills and capacity, and determine where you need external partners to fill gaps. This will help create a feasible project roadmap, reducing the risk of overburdening your team and making mistakes.

7) What Does Your CFO Say?

Some companies opt to record their website development costs as capitalized software, amortizing the expense over three to five years. Others choose to expense these costs as they are incurred.

The way you report this – a capital expenditure vs. an operational one – will influence whether you should execute a complete rewrite or upgrade iteratively.

Future budget should also be considered. Do you have funds allocated for data and customer growth to support future expansion if your data volume increases or you gain more customers? Thinking about future needs and having the budget in place will contribute to a more sustainable upgrade.

8) Who Will Own Your Change Management Plan?

Effective change management in a Sitecore upgrade can significantly boost success, ensuring you fully leverage new capabilities while minimizing disruptions. User adoption, training and support, process alignment, and clear communication to impacted team members are crucial.

Do you have IT personnel who understand the scope of an upgrade, its impacts, and can manage this change? Do you have an Enterprise Architecture practice or Systems Architect to develop a growth plan, decide on horizontal or vertical expansion, and advise on alleviating CX or business issues through expansion?

An upgrade partner can greatly assist your change leader in proving an expansion plan and exploring options.

9) How Will This Upgrade Affect Your Other Services?

Ancillary services you’ve integrated with Sitecore cannot be forgotten when planning your upgrade.

Will those integrations still be necessary? Will other solutions need to be updated? How will the data and analytics shared between solutions be impacted?

Answering these questions and more will help create both a roadmap for updating your other services and a mitigation plan if the outside resources can’t work on your schedule.

Upgrade With the Right Partner

All of these answers need to be considered and woven together to create your unique Sitecore upgrade strategy.

Sitecore Silver PartnershipAs a Sitecore Partner, our team can guide you through each phase of the upgrade – strategy, roadmap creation, and technical execution – to guarantee a successful implementation. Our combination of technical and customer experience expertise ensures you are achieving your business and customer experience objectives throughout the upgrade process.


If you’d like to discuss how G2O can work with you and your team to realize the power of Sitecore and truly transform your Customer Experience, please reach out. We’d love to learn about your specific situation and how we can help.