A Guide to Digital Transformation Road Mapping


If you talk to anyone who has spearheaded the digital transformation of an entire organization, they will never say that it was easy. They may even regale you with their digital transformation war stories or situations that seemed impossible to navigate. But if you ask them, "Was it worth it?" the answer will always be, "Yes."

Anything with the word “transformation” in it should indicate that it won't be easy. Transforming equals change, and most people resist change. That's why we think digital transformation is like climbing not just one mountain, but many moutains. Each climb to the summit should be 15 to 18 months. It is useful to divide each digital transformaiton climb into quarterly basecamps with clearly defined goals centered around a theme.

A digital transformation roadmap should be a one-page document that you can share with the organization. The roadmap should be easy to understand and clearly state what digital transformation will do for the organization and why you are doing it. You can lay out your one page document in several ways, but it should have the following components.

Develop a Clear DX Vision

Have a clear definition of what digital transformation really means for your company. For example, you could say something like, “Digital transformation will help us leverage our technology throughout the company to change how our business works so that we can deliver value to our members.” This sounds like a typical vague statement, but what does it really mean? Challenge yourself to write a DX statement that more clearly defines what you will do for your organization. This DX vision statement, although lengthy, does provide a clear vision and scope: “We will achieve digital transformation by implementing a centralized engagement layer that will provide real-time interactions that anticipate both employee and member needs and provide smarter solutions on-demand. DX will increase productivity and operational efficiency and build meaningful and purposeful relationships with our members.”

The overall digital transformation vision could span over multiple climbs whereas your basecamps should be centered around a theme that are quarterly. An example of our themes might be Basecamp 1: Connected Website; Basecamp 2: Connected Branches and so on.

Map Out Your Data Integrations

Data and integrations are the key to successful digital transformation and therefore should be a critical piece of your digital roadmap. For each basecamp you will need to understand what vendors you will want to put into your tech stack to support your vision and themes. For example, does an integration cloud or data management platform make sense for your organization’s tech stack? What about integrations with vehicle search vendors or mortgage rate systems to support website personalization and real-time updates? Each integration has to be outlined, and you need to decide what data will be pushed and pulled through API's. What types of information will you need from your core systems and lending applications? Will those fields need to be in real-time or is a daily push of data enough? The answers depend on your vision and what your organization is trying to achieve.

Assess Your Technology Stack

Digital transformation will need more than your current systems. Depending on your organization's DX vision statement, partnerships with existing vendors will probably not be enough. You will likely need other products to deliver your digital experience, like cloud scheduling, chat and text, and perhaps even a new content management system that can do website personalization. You might also strongly consider choosing technology that will allow you to start leveraging machine learning and artificial intelligence.

Craft Well-Defined Goals

It is important to define what you hope to get out of your digital transformation. Defining this at each basecamp helps keep your organization focused. If you have a theme attached to each basecamp, it makes it easier to understand the transformation happening at each stage and associate it with your DX goals such as increased production, decreased expense, enhanced member or employee satisfaction, or a combination of goals. You might have high level dashboards for the overall DX vision as well as your anticipated outcomes for each basecamp. For example, Basecamp 1 might have an outcome of increasing website leads by 50% and funded loans by 15% over one year.

Anticipate the Cost

Digital transformation can be very expensive and will likely require new technology and resources to help you achieve the most out of your DX investments. Start with basecamps that are easy to deploy but have high impact so that your team gets excited about what digital transformation can do for the organization. Set a realistic budget. The cost of your digital transformation will depend on several factors such as how aggressively you want to transform your organization or the number of members and employees you have. It is common for digital transformations of this magnitude to cost up to seven figures over multiple years.

Develop Your DX Timeline

Breaking your digital transformation into 15- to 18-month journeys with quarterly checkpoints or basecamps helps the organization consume the transformation over time, and it helps control costs. Agile project management helps your organization build a better digital transformation approach because it allows you to fail fast and iterate.

Create Beta Teams

This is probably the most important point we can make in this article. Iterating and deploying beta teams for each basecamp is critical to your success. Trying to deploy a basecamp that is transformational to the organization without a small beta team to test over a few weeks is a mistake (which we have made in the past). There are many issues that have to be fixed before you deploy to the larger group of employees or members. The beta team should be employees who are excited about change, willing to collaborate and share issues, and who are experts in the area you are transforming so they can help predict problems.


True digital transformation should involve the entire organization. Yes, it will be challenging with many roadblocks and unforeseen challenges, but it will be worth it in the end. Happy climbing!