SaaS Product Website

Company: Truth Technologies


Roadmaps are a tricky thing. They’re supposed to layout an often multi-year plan for how your product and/or technology will evolve, and include things like projects, milestones, and alignment of major initiatives. The problem is, unlike those physical highway roadmaps, technology is ever changing. Remember, too, that the business is continually responding to change.

Yet, roadmaps do provide a valuable service, if you understand how to use them. My opinion and approach to roadmaps is that they exist to frame conversation, debate, and eventual decisions for your projects. There’s something about putting it down in visual form that gets you further down the road.

So, my first iteration of a roadmap is generally the most opinionated one, where I do the dirty work of trying to fit everything together. Occasionally, it simply works out and the first draft sees a long life, but more often it gets people thinking about how they view the road ahead. That’s a good thing.


Sketch Visio

My contribution

Management 80%
Authorship 80%


roadmap program management transformation



The objective here was to provide a roadmap for our digital product and technology projects. Sounds simple, doesn’t it? Not quite. These projects were a collection of both large and small, straightforward and complex, and custom developed and pre-packaged. Not every large project was complex, and not every small project well defined. And all were critical!

Approach & Process

Gathering Phase

The approach was a bit of grunt work to assemble project lists, work with stakeholders on justifiable scope, drafting project packets, and campaigning for approval. Oh, and we’re not even at the technical architecture yet!

Nevertheless, the first phase came together quite well.

Next came the architecture design sessions to get at least some high-level concepts defined so we could educate stakeholders on the possible solutions. (Gross) estimation followed.

Build Phase

Once all the necessary information was gathered, I drafted three views of the roadmap.

  • The primary visual was one that laid out projects within distinct categories and across time.
  • The second was very similar but grouped projects into stages of a long-term business strategy, specifically around digital enablement for our platform.
  • Lastly, there was the manager-friendly spreadsheet that listed every project and some metadata PMs love to see.

Tools & Techniques

  • Issue management (for roadmap forecasting): JIRA + Portfolio + Tempo
  • Cost estimation, budgeting, & forecasting: Microsoft Excel
  • Drawing: Sketch + Microsoft Visio