Cait Smith
Cait Smith
February 7, 2017

Digital Roadmap 101: Building a Roadmap That Evolves With You

“Planning is bringing the future into the present so that you can do something about it now.”

I’m a sucker for good quotes, and this one by Alan Lakein brilliantly simplifies an often-misunderstood concept: the role of a digital roadmap.

Digital has disrupted the way businesses interact with customers across all industries—from retail to insurance. We experience continuous waves of disruptions like rolling earthquakes. Some are big, some small, some hardly noticeable. Many businesses are eager to invest in anything that manufactures artificial certainty within their organizations…certainty that they’ll remain competitive, grow and thrive.

Issue #1: There’s no such thing as certainty.
Issue #2: This often results in “cool hunting” (i.e. chasing down trends without first identifying a true problem to solve).

Rather than cool hunting, at PointSource we encourage our clients to build a digital roadmap.

A digital roadmap is the foundation upon which organizations plan, build, execute and measure the impact of digital initiatives on their long-term vision.

What It’s Not

We commonly hear, “How do I build a roadmap that stays relevant when customer behaviors are always changing?”

This is a fair question, but it’s built on a hefty false assumption: that a digital roadmap is static. Your digital roadmap is not just a PowerPoint that’s presented during a meeting, then dies a slow death on the company server. Nor is it a tactical step-by-step set of instructions, like you’d get from Google Maps or Siri. It’s not a project plan and definitely not a requirements list.

What It Is

It’s a living tool.

A digital roadmap is like any strategic instrument, it requires tuning. It needs built-in feedback loops and ongoing measurement so it can be adjusted and iterated upon, as needed. It should be flexible enough to respond to signals of change in customer behavior and within the market.

In sum: Your digital roadmap is a sense-making tool that helps cross-disciplinary teams understand where the organization is now, where it wants to be in at various points in the future, and the pivotal benchmarks required to get there.

Keep Your Roadmap Alive

There are four elements necessary to ensure your roadmap continuously evolves with you, that it stays alive and functional. It must be:

Ensure your roadmap showcases goals, not just tactics plotted on a timeline. Don’t be overly prescriptive with long-term tactics (i.e. tools, apps, features, technology, programs), that way you can change/modify proposed tactics in response to what you learn about customers through research and measurement.

That means your roadmap should work in tandem with and support of your organization’s business strategy. There is no solid business strategy today without a digital heartbeat. 

Focus on prioritizing and measuring initiatives that will positively impact specific customer behavior. We suggest starting where you can have the greatest positive impact the fastest. This often means focusing on incremental activity-based behavior change (e.g. increased site engagement), but it should ladder up under larger business objectives (X% increase in year-over-year renewals).

Ensure your roadmap is shared and visible across teams, with a method for teams to contribute, comment and ask questions. Your digital roadmap is a catalyst for influencing culture, one where employees are invested in the future of the company and have enough context and freedom to come up with new ideas and suggestions to impact goals.


Sound like fun?!

Sound a little messy but exciting nonetheless? We think so, too.

If you have questions about how to build a digital roadmap, let’s talk. Want to learn more about PointSource’s digital transformation strategy? Start by exploring these four questions that we believe are at the core of digital transformation.


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