A Guide to Strategic Roadmapping

If you’re familiar with Rootstrap, you’ve probably heard us talk about Roadmapping.

In many ways, Roadmapping is our signature service. Not only is it one of our flagship offerings, but it also embodies our ethos as a company. Our Roadmapping workshop is what really got Rootstrap off the ground, and over the years it’s evolved to influence every aspect of our products, our services, and our organization. We bring the techniques and concepts that make Roadmapping work into our mobile app development projects, our growth user acquisition projects, and everything else we do. Whether we’re building a mobile app in Phoenix or at our office in New York City,

But what exactly are we talking about when we talk about Roadmapping? For us, Roadmapping is a service that we offer: it’s a two to four week product development boot camp where we hone the concept behind a digital product, validate it in the marketplace, and create a product backlog – a literal roadmap to full development. 

But the broader concept of strategic roadmapping applies far beyond mobile app and digital product development. Strategic roadmapping can apply to a product, a project, or an entire company.

What Is Strategic Roadmapping: A Definition

Before we really dive into the tactics and strategies, let’s answer a simple question: what is strategic roadmapping?

Speaking broadly, strategic roadmapping refers to any process of planning out a figurative “roadmap” for something. It involves analyzing the current state of the world, making educated guesses about how the situation will continue to evolve, and laying out a roadmap for future action that you believe will succeed based on the current situation and the ways you think that situation will change. 

Critically, strategic roadmapping takes place at the level of strategy, and not necessarily at the level of tactics. In other words, strategic roadmapping is about forecasting broad trends, then creating a high-level plan for moving through those. That doesn’t mean working out the gritty details of an action plan months in advance. Instead, it’s is focused on identifying high-level priorities, forecasting larger trends in the marketplace, and creating a general plan for how to achieve those goals in light of reality. 

The roadmap itself will look different depending on what’s being roadmapped. For a digital product, a roadmap can take the form of a detailed feature list, a go-to-market plan, or even a set of user profiles and a strategy for reaching those users. For a company, a strategic roadmap may involve key milestones, as well as a strategy and timeline for achieving them. The specifics of the roadmap are malleable – what matters is creating a plan that’s grounded in the realities of the current market or situation. 

To better understand strategic roadmapping as a concept, let’s look at a few examples. 

What Does Strategic Roadmapping Look Like: Strategic Roadmap Examples

Our Roadmapping workshop is an example of product roadmapping. We take digital products, as well as the companies behind them, and we follow a framework to achieve the following things:

• Hone the concept of the app and understand the key value proposition
• Identify the target user
• Create a go-to-market strategy for reaching and converting those users
• Create a clickable prototype of the finished product
• Build out a product backlog – a step-by-step roadmap to full development

Because our roadmapping applies to digital products and we often work with first-time entrepreneurs and product owners at the start of the dev process, our process aims to optimize the app for success given the realities of the marketplace, then create a plan for attracting users and getting the app off the ground. We go about this using a 4-step framework:

Step 1: Define

Our first objective to get clear on what, exactly, the mobile app does. If this product only did one thing, what would that be? What’s the single most important benefit that the product creates in the lives of users? Before we can create the rest of the roadmap, we need to have a laser-sharp understanding of what it is we’re roadmapping in the first place. 

Following that, we work to explore the marketplace. What competitors exist for this product? How are those products similar to our own, and how are they different? What do our competitors do well and where do they fail? Are users satisfied with the existing options in the market? What are our opportunities to attract users to our own product? 

In essence, this step is about understanding the app and its position in the marketplace. Once we get a clear understanding of what the product does, who it’s for, and where it exists in the current market, we can move onto the specifics of how we’ll create the product and bring it to market. 

Step 2: Sketch

With a core understanding of the product, it’s time to get to specifics. During the sketching phase, our objective is to understand all the different ways we could structure and build the product. This is about throwing paint at the wall: we need to explore the full extent of the solution space. Our goal is to explore a lot of different ideas in terms of how to make the product real so we can identify the one that works the best. 

During this phase, our focus is on the user. As we evaluate potential approaches to structuring the product, we refer back to the work we do in step one. Ultimately, we’re trying to find a way to build the app that best serves our target user and improves on the existing competition in the marketplace. From there, we can start to outline exactly what it will take to build the product. 

Step 3: Prototype

Once we decide on a fundamental approach, we work to solidify the design and architecture of the app. In the third step of Roadmapping, we’ll create a high-fidelity, clickable prototype of the finished product, complete with wireframes and branding elements. 

At the end of prototyping, we walk away with a fully-realized “model” of the application. Every screen is included, the branding and design are completely worked out, and users can interact with the prototype – the only thing that’s missing is functional code. 

We do this for two reasons. First, it’s a cheap way to do a “dry run” of building the app. Prototyping allows us to see firsthand what works well and what needs improvement within the app. We can get a true feel for the finished product, but we don’t have to spend the (often hundreds of thousands in) money for development. 

Second, a prototype allows us to bring the product to real users before we even begin the development process. With a clickable prototype, we’re able to have users interact with and give feedback on the product before we write a line of code. That’s incredibly powerful for making sure the final mobile app is truly ready to succeed in the marketplace. It allows us to make revisions on the design without spending money on coding – so when we do start full development, the product is ready for it. 

Step 4: Refine & Prep

In the final phase of our strategic roadmapping process, we put the finishing touches on the product and do everything we need to prepare it for development. One of the biggest parts of that process is creating the product backlog. 

A product backlog is essentially a very detailed feature list. It’s a comprehensive database of every single element needed to build the finished product, all written in a format that Agile development companies can understand. Once every “box” in the backlog is checked, the app is finished. In this way, it’s very literally a “roadmap” to development. 

The backlog is also important because it allows going through a process called backlog grooming. During grooming, we work to identify the bare minimum feature set necessary to create a functional app. This is the v1.0 of the product, or the minimum viable product (MVP). We’ll also prioritize the backlog to outline what needs to happen to finish the v1.0, the v1.1, the v2.0, and any other subsequent releases of the product. 

Why do we do this? It’s a massive cost saver. We’re often able to cut a development budget in half with just one session of backlog grooming, which allows us to get the product in the hands of users cheaper and faster. From there, we can collect user feedback and further optimize the product. 

Grooming also allows for more focus during the development process. In a sense, it’s a way to mark the path for our roadmap: it lays out what we need to build to get to the first iteration of the product, where we go from there, and all the milestones that follow. This prevents lost time and wasted effort during development sprints.

This is our approach to strategic roadmapping. Our process is specifically geared towards digital products, so it won’t apply to everyone. But there are a few takeaways to notice. 

Our approach starts by learning as much about the world as possible – we need to understand the situation as it is, so we can build a roadmap through it to get to our goals. This is why we’re insistent on understanding the core benefit of the product, the target user demographic, and the existing competition in the marketplace. If we create a roadmap based only on our own assumptions, we can expect to fail. 

This principle applies anywhere. Too often, people approach roadmapping with only the ideas in their heads. They assume they understand the actual goals of the business and the best way to get there, and this leads to unpleasant surprises down the road. The first step of any strategic roadmapping process should be to learn about the state of the world, without bringing in pre-existing biases. 

We also focus on making the end result as real as possible, as early as possible. On one level, we create a prototype because it’s a useful asset – but more importantly, prototyping forces us to get very clear on our ideas. It’s easy to say that the app will have an intuitive screenflow, but that statement is almost meaningless in practice. The only way to understand what makes the screenflow intuitive is to sketch it out. Prototyping forces us to make our ideas real, which often throws light on ambiguities and contradictions before they cause problems. 

And finally, our roadmapping process produces a literal roadmap. Through the development backlog, we create a step-by-step roadmap for getting the thing built. It explains exactly what needs to get done, in what order, and for what purpose. While roadmapping should be strategic and shouldn’t attempt to create a daily schedule, months in advance, it should provide a feasible, actionable path to the final product. 

All of that said, ours isn’t the only approach to strategic roadmapping. Truthfully, a strategic roadmap could take any form, and the process could change drastically depending on the goals of the project. In some cases, a strategic roadmap may be a marketing plan. This may take the form of a long-form document summarizing the market, coming trends, and the specific channels that the marketing team will use. 

A strategic roadmap could also be a content calendar. This might include the types of content to be created, topics and assets for content creation, and the intended outlets for the content. This may be a comprehensive document or could be as simple as an Excel spreadsheet. 

Another common format for strategic roadmapping is a business plan. This might include market research, a mock-up of the product or a description of service offerings, and a timeline for launching the business and hitting key milestones in the growth of the company. 

The literal form of the roadmap can and should change depending on what’s called for, but what remains constant about strategic roadmap is their intention and their function. Strategic roadmaps should de-risk the venture by outlining the goals of the project and presenting an actionable, data-backed plan for reaching those goals. 

Why Is Strategic Roadmapping so Important: Benefits and Goals

So now we know a little more about how strategic roadmaps work. But why would companies want to roadmap in the first place?

In our experience, the benefits of roadmapping are massive. The data on our past Roadmapping clients alone backs this up. 

On average, 18% alumni of the Roadmapping program raise at least $250,000 in pre-product seed capital. Of that subset, roughly 8% raise more than $1,000,000 in capital. Compared to the average startup, this means that Roadmapping gives our clients a 2,600% increase in the likelihood of getting funded. 

Even for clients that don’t get funded or don’t launch the product, Roadmapping still often generates a win. Sometimes, our Roadmapping process tells us that in the end, the product probably won’t succeed in the marketplace. There may not be enough demand, the competition may be too steep, but whatever the reason, we see that the venture is a bad idea. 

In those cases, though, we come to that conclusion after less than 4 weeks and with only a fraction of the money that full development would require. Normally in app development, you don’t really find out if your product will succeed until after you’ve built it. This means betting months of your life and hundreds of thousands of dollars on something that could ultimately fail. 

With Roadmapping, we can avoid those expenditures. This means the client finds out the product will fail before spending all that money, which leaves them with resources to pivot. Whether the product ultimately fails or gets vetoed in the early stages, Roadmapping still produces a benefit. 

These same benefits apply whether you’re roadmapping a digital product or a marketing plan. In essence, strategic roadmapping allows you to evaluate success before you begin the process. In this way, it de-risks the investment in the project. It allows you to spot flaws early on, when you still have time and resources to fix them – instead of when you’re 4 months in. 

Roadmapping also helps to prioritize the project and identify what’s truly essential and what could be dropped, if necessary. You sketch out what it will take to achieve your desired goal, and through that process, you can identify the things that aren’t all that important when push comes to shove. Often, this translates to improved efficiency and cost savings. 

Another advantage is that roadmapping gives you, very literally, a roadmap. It outlines what needs to happen to fulfill the project goals, the way you’ll accomplish those things, and the order in which you’ll do them. This keeps the entire process more focused and more efficient, preventing confusion and wasted energy later on. 

Perhaps most importantly, though, strategic roadmapping gives you a chance to test your ideas before your put them to use. It allows the team to think through the problem in depth, giving the solution-finding process the time it deserves. It forces you to think critically about your ideas and put your assumptions to the test. They say the best way to test your understanding of a concept is to try to explain it to someone – and in some ways, the best way to test the viability of a project is to try to roadmap it. 

Those are some of the benefits of strategic roadmapping. But if you choose to do a roadmapping session yourself, what will your goals be? As we’ve mentioned, the specific goals of roadmapping vary greatly from project to project. But on a high level, these are a few of the most important things to achieve through strategic roadmapping:

• Gain an in-depth understanding of the “world” of the project (the market, the situation, the competition, all players involved)
• Clearly identify a set of objectives that further the overarching goals of the organization
• Test all assumptions against your understanding of the goals and the marketplace
• Outline a step-by-step “roadmap” for completing the project
• Define the finished product and/or desired end state
• Prioritize objectives to identify what’s most important to the success of the project
• Create a timeline for the project complete with milestones

Your own roadmapping goals will depend on what it is you’re roadmapping, but these general points can help inform the specifics of the project. 

What Strategy Roadmap Tools Currently Exist

So what are the tools available to you for creating your strategic roadmap?

As it turns out… there are plenty. 

One of our first recommendations would be Mastering Project Roadmaps, an e-course put together by Brennan Dunn of Double Your Freelancing and our own cofounder, Ben Lee. This isn’t a roadmapping tool in the literal sense of the word, but it’s one of the best ways to get a comprehensive, actionable understanding of how to do roadmapping for yourself. 

The course is geared towards freelancers and agencies, and it goes much more in-depth on all the topics we cover in this blog. It also includes downloadable summaries, templates, worksheets, and other material to help you create a purpose-built roadmapping strategy from the ground up. 

But what if you’re just looking for a tool to help you build roadmaps? Thankfully, those are in abundant supply.

ProductPlan is a visual roadmap planning tool specifically designed for products. It has a simple interface and a visual layout, making it a great tool for creating strategic roadmaps quickly. Simplicity is a major advantage here – the simpler a product is, the most likely you are to lose it. ProductPlan can help you get your roadmap started in minutes so you can start making progress as quickly as possible.

Another tool available is Roadmunk. Roadmunk is similar to ProductPlan in that it offers a simple, visual interface for creating strategic roadmaps, but Roadmunk offers a little more flexibility and a more robust feature set. In addition to digital or physical products, Roadmunk is designed to work for other types of strategic roadmaps like business roadmaps, project roadmaps, and marketing roadmaps. Roadmunk also offers two view options: a timeline view, which shows tasks and milestones arranged linearly on a timeline; and a “swimlane” view, which arranges tasks on a kanban-style board. This is powerful for giving everyone on the team both an overview of the full project and an understanding of the specific tasks at hand. 

Outside of purpose built roadmapping tools, you can also use more general project management and organizational tools to create your strategic roadmap. At Rootstrap, we regularly use Trello to keep track of our development process, and it’s a great tool for roadmapping as well. Trello is project management program that works by arranging cards into lists and boards. Each card represents a task – it may be preparing a presentation, coding out a specific feature, or any other quantifiable action. These cards are arranged into lists and can be moved freely between these lists, making it easy to identify the tasks you’re working on, what you’ve already completed, and what you still have left to tackle. Finally, lists are housed under boards – allowing you to create different sets of tasks for different departments or split up tasks by project. 

At Rootstrap, we’ve also built our own roadmapping tool specifically for digital products: Arbor. Arbor is an online tool for creating product backlogs, so it’s specific to digital products. That said, it’s one of the most robust backlog managers out there. It’s an excellent option if you want a simple, powerful way to arrange your product backlog, and seamlessly exports to Trello so you can turn that backlog into an actionable roadmap. 

Ultimately, most project management tools can work as a roadmapping tool. If you or your team is already familiar with a particular project management application, the best option is often to simply use that to create your roadmap. But if you want a dedicated program for creating roadmaps, any of these tools can help. 

Are Strategy Roadmap Software Packages Worth It

Arbor is free and Trello works on a freemium model, but not all strategic roadmapping tools are so affordable. Robust, enterprise-focused project management applications can easily cost hundreds of dollars per month. So are strategic roadmapping software tools really worth it?

In our opinion… kind of. For a company with a serious need for an effective, easy to use, and fast roadmapping application, paying top dollar for premium software can make a lot of sense. So long as that investment is being made up for by increased efficiency and better decision making, a strategy roadmap software package can absolutely be worth it.

That said, our advice is to save money if at all possible. Sure, getting a dedicated piece of roadmapping software can make it easier to roadmap. But with the plethora of free and cheap options on the market, we’d normally recommend just using something that works and spending money on the project itself. 

Most of the benefits of roadmapping come from the exercise of thinking critically about the project, forecasting what lies in the future, and putting your assumptions to the test. Software can help make that process faster and can help you create a more visually appealing finished roadmap. But ultimately, what matters is to ask the hard questions. Software can’t do that for you. 

We encourage you to think of strategic roadmapping tools as just that: tools. They can help make your roadmapping process faster, more efficient, and prettier. But at the end of the day, it’s you doing the roadmapping. Not the tool. That’s important to keep in mind when evaluating any strategic roadmapping software package. 

Strategic Roadmapping by Rootstrap

There are plenty of tools and templates to help you do roadmapping on your own – but to get the most out of strategic roadmapping, it helps to enlist the help of experts. At Rootstrap, we’re not just experts: we built our company around Roadmapping. 

Back when Rootstrap was still Neon Roots, we had an idea for a different approach to mobile development. We’d seen countless entrepreneurs spend hundreds of thousands of dollars to build a mobile app, only to discover there was no market for it after launching. We started our Rootstrap Roadmapping service to solve that problem and help entrepreneurs find out if the mobile app was viable before building it. 

Roadmapping was a huge success, and we’ve helped more than 500 founders launch digital products through Roadmapping. Our metrics speak for themselves:

• 18% of Roadmapping alumni raise $250,000+
• 8% of alumni raise more than $1 million
• Roadmapping alumni have raised over $500 million in aggregate capital
• Roadmapping boosts alumni’s chances of funding by roughly 2,600%

Roadmapping is an inexpensive way to determine the feasibility of a digital product before shelling out huge money for development. And if you’re interested in trying Roadmapping for your own product idea, we’d love to help. 

Drop us a line and tell us more about what you’re looking to do. We don’t bite, and we’d love to talk with you to see if there’s a mutual fit. 

Let’s make something great together.