Roadmap Strategy

How to Build a Roadmap

Building a Digital Strategy Roadmap

This guide will help you create and develop your own digital strategy roadmap. It includes tips, recommendations, and best practices from leading digital commerce agencies.


Building a digital strategy roadmap

01 Setting goals

Business goals are often already in place and relate to revenue or market share targets. The key part is understanding which digital areas and activities support these targets. In larger teams, a democratic approach is recommended, where other teams, like strategy, content, experience, UX, and IT, contribute towards setting appropriate goals to achieve the desired outcome.

This process begins with visualizing the celebration after achieving your biggest goal. In this exercise, team members think about what needs to be achieved to reach this goal. A simple voting process and collection of findings can produce clear patterns and ideas on where to start setting goals.


Goals should follow the simple SMART rules:

• Specific, measurable, achievable, realistic and time-bound
• Goals should clearly state the baseline or current statistics, the future objective, and when you expect to achieve them
• Look at goals from short-term, mid-term, and long-term perspectives

Short-term goals (quarterly):

• Grow customer base from 20,000 in Q1 to 22,000 in Q2
• Successfully implement the new Content Management System on time and within budget
• Grow your brand product mix from a 25% contribution to 50% by the end of the financial year
• Improve content creation cycle from 7 days to 2 days by the end of Q2
• Increase content publishing from 2 articles a week to 4 articles a week by the end of Q1
• Improve content engagement e.g., time spent on a page, pages per session, likes and shares
• Increase page views and visitors

Mid-term goals (annual)

• Increase B2B revenue contribution to total revenue from 30% in June to 50% in the next 12 months
• Successfully launch a new Ecommerce platform on time and within budget
• Improve Customer Experience Net Promoter Score from 7 to 9 by the end of the year

Long-term goals (2-5 years)

• Grow own brand product mix from 25% contribution to 50% by the end of 4 years
• Introduce product customizations on the site for customers to personalize their products
• Introduce a Product Information Management tool


There’s no rule regarding the number of goals, but avoid setting too few and making the strategy vague. On the other hand, you should avoid setting too many goals and obscuring the focus on crucial goals. Once your short-term, mid-term, and long-term goals are defined, make sure they are shared and kept visible.
Goal-setting is also about defining the process, communication, and ways of working that will ultimately facilitate success and growth.


Do: Create a digital content strategy

As a part of your overall digital strategy, it’s important to also create a specific digital content strategy. A digital content strategy describes how a company produces high-quality content for their target audiences and personas in a repeatable, reusable way that produces consistent experiences throughout the buyer journey and across digital channels. It helps define workflows, inform the content model, and unify content operations across the business for more efficient content creation and distribution.
Your digital content strategy is the thread that weaves together a vast amount of content into a unified plan. It breaks down silos and connects different types of content — blog posts, video content, webinars, infographics, landing pages, online tutorials, social media platforms, ecommerce sites, podcasts, mobile, voice, IoT, digital billboards, etc. — to produce seamless user experiences.
Most companies have some components of a digital strategy already in place. Ask yourself a few of the following questions to identify and unify the strategies your organization already has, fill in any gaps, and produce a digital content strategy that serves your needs and takes advantage of modern technologies.

• What are our high-level goals?
• What existing content do we have, and is that content doing what we need?
• What content processes and workflows do we currently have in place, and are they effective?
• What tools exist that will help us build a tech stack to deliver on our priorities? Do these tools integrate with our existing technology investments?
• How will this digital content strategy facilitate new ways of working for our digital teams and allow them each to spend time on the most valuable initiatives?

Don’t: Start building a tech stack that won’t serve your future needs

If you try to “freestyle” this part of the process and start making big technology purchases without a digital content strategy in place, you may find that you end up with a tool that won’t get you where you need to go in six months, let alone in the next 3-5 years.
Future proof your investment by choosing a composable content platform that fits into your overall digital strategy and is able to deliver to any digital channel and can integrate easily with the tools you want to use.
Identify what tools you have, which ones you want to add or replace, and what your timeline for change looks like.


02 Defining KPIs

To celebrate success, you must define success early on. One of the best ways to do this is by ensuring stakeholders define and understand your digital strategy roadmap through Key Performance Indicators (KPIs).


What is a KPI?

A KPI is a metric with a target integral to your business’s success. Every company has goals and objectives, which usually touch on financial performance, customer satisfaction, operational efficiencies, etc. KPIs track the efficacy of goals and ensure that the roadmap’s planned activities move the right areas of a project forward.

Frequency and duration

It’s important to know how often to track KPIs. The evaluation frequency reveals new opportunities and even finds different ways to achieve your goals. The following frequencies are used when tracking KPIs:
• Live (tracked continuously)
• Daily
• Weekly
• Monthly
• Quarterly
• Bi-annually

The duration of your KPIs is just as important as the frequency of tracking them. It’s important to set short-term and long-term KPIs. Locating your immediate targets and envisioning the road ahead gives a complete strategy overview.
Start with long-term KPIs and work backward to define the short-term targets. Once you set your short-term KPIs, you will notice that they give rapid feedback on your performance and time to course correct. Leave room to reevaluate KPI targets and be realistic about performance and what you feel is achievable going forward.

Setting KPIs

As one of the foundational aspects of your digital strategy roadmap, KPIs propel your business forward. But first, ensure you have clearly defined what the KPIs are. Usually, they are known and well-used metrics attached to customer experience and financial performance. They can also be based on time and cost savings if they are integral to your business.

Here are some examples:
• Revenue
• Conversion rate
• Customer lifetime value
• Net Promoter Score (NPS)
• Customer satisfaction
• Average order value
• Time on the site
• Customer service ticket rate of resolution


Next, set a baseline. This means capturing the metric as-is or in its current state. From there, you can set your short-term and long-term targets. In some instances, ambitious targets can be used to motivate teams to push further. Finally, attaching a timeline to your targets and KPIs is critical.
A good approach is to use the following and fill in the blanks:
Increase/ Decrease (KPI) from X (baseline) to Y (target) by Z (date) = Increase turnover from £1M to £2M in the next 12 months.

Setting KPIs


All KPIs should have an owner responsible for monitoring KPIs and achieving the targets set. KPIs need continuous grooming and assessment. KPIs can also be associated with an individual’s performance. This can directly and positively impact your targets and business goals. Finally, it’s important to remember that KPIs can fail. Some common reasons for this are KPIs lacking specificity and not being defined properly. KPIs can also fail when it is unclear how to measure them. Ensuring access to the data you need and determining the data source upfront is critical for alignment. Lastly, make sure your KPIs are achievable. Looking at short-term and long-term targets at the right frequency will help you understand if you are on the right path.


Do: Keep your digital strategy roadmap flexible

One of the most important things you can do when creating your digital strategy roadmap is to keep it flexible. While it’s important to have a plan in place, the digital landscape is constantly changing, and you need to be able to adapt to these changes quickly. Instead of creating a rigid plan that is difficult to change, focus on creating a flexible and adaptable roadmap. This means breaking your plan into smaller, more manageable pieces that can be
adjusted as needed. It also means being open to new ideas and approaches and pivoting when necessary.

Don’t: Overcomplicate your digital strategy roadmap

While having a clear and comprehensive digital strategy is important, it’s equally important to avoid overcomplicating your roadmap. A roadmap that is too complex can be difficult to understand and communicate, and it may lead to confusion and delays. Instead, focus on creating a roadmap that is clear, concise, and easy to understand. This means avoiding technical jargon and using language that is accessible to everyone. It also means prioritizing your goals and objectives and focusing on the most important steps you need to take to achieve them.


03 Activities & projects

The next step in developing your digital strategy roadmap is identifying and planning activities and projects to achieve your goals and targets. At Vaimo, we engage with clients at different stages of their roadmap development. As a result, we’ve developed two tailored scenarios to meet our clients’ varying needs and ensure any work already completed in this area is considered.


Scenario 1 – No clear backlog or idea of what projects and activities are required

In this approach, we work with the client to find gaps and opportunities. These are discussed and planned with the vision, goals, and success factors in mind. A critical aspect of succeeding in your strategy is ensuring sufficient projects and activities support your overarching business and website goals.

In this scenario, we use tools such as our Digital Readiness Assessment and the Customer Experience Rating to review key areas of the business, people, processes, and website experience.

Digital Readiness Assessment and the Customer Experience Rating

Scenario 2 – The client has an idea of what key projects and activities are required

In our second scenario, the client will give us an idea of the key activities and projects to be implemented. We then help them validate those activities against their goals and success factors and prioritize them based on a cost-benefit analysis. Following the analysis, we can start to prioritize activities and projects.

Validating and prioritizing activities is no small feat. We start by identifying activities that require validation. This could be through testing, data analysis, or market research. Once an activity or project is validated, it will become an activity to implement. At any point, you might have a list of activities you’re busy validating through testing and data analysis (while implementing the backlog items from your implement list). Once activities and projects are defined, you will need a straightforward way of prioritizing them so that you implement the high-impact activities and projects first. At Vaimo, we use a planning board to do this. The planning board is based on cost vs. benefit analysis and considers predetermined factors that have been weighed in importance.

For example, benefit factors might include increased revenue, customer value, and strategic value, and cost factors might be implementation effort, operational cost, and risk. We define these factors and weigh them according to their importance. Once this is done, we score each activity based on its impact on the factors. The outcome is a score for each activity that the impact on the overall goals can rank.

It’s important to align your activities with the KPIs you originally set out so that your projects directly impact your targets. Additionally, monitoring your KPIs and their progress will help you prioritize your activities and projects continuously. KPIs are often difficult to measure at an activity and project level, and we usually recommend setting and measuring these against your goals and success factors.


Do: Focus on the users – end shoppers and business users

Start by identifying the pain points in your current systems and processes. Collaborate with your team to understand which tasks are time-consuming and look for opportunities to streamline these processes. Next, consider integrating AI-powered tools into your product discovery systems, such as natural language processing for on-site search, dynamic product recommendations, and personalized marketing campaigns. Ensure that these tools are user-friendly and accessible, even for those with limited technical expertise.

Don’t: Neglect a holistic integration of AI solutions

AI-driven features shouldn’t be treated as isolated entities. Instead, they must be seamlessly integrated into the overall user experience, complementing and enhancing each other. By doing so, we can drive customer engagement, improve team efficiency, and ultimately, boost revenue. Using this approach also helps you add new services when innovations disrupt the market. For example, making it easy to quickly add an ecommerce AI chatbot that is already trained on your ecommerce data and integrated with your search and merchandising.


04 A thematic high-level plan

While not critical in the overall process, this plan gives a great high-level view of the investments required by an epic or theme and a quality overview of the key projects to be undertaken monthly. This view helps senior management and C-suite executives to better understand where investments are made and the desired impact and ROI.

Firstly, you need to identify the emerging themes in your activity planning. These are the themes that your roadmap will be based on. We see
some common themes emerge across many of our clients, some of which are described below:

• Improve on-site performance
• Optimize search and SEO
• Enhance personalization
• Enhance customer experience
• User experience and content optimization
• Checkout optimization
• Lead form optimization
• Grow omnichannel capability
• Increase automation and efficiencies
• Mobile optimization

Themes are groupings of similar activities, projects, or initiatives. Ideally, your themes should describe some type of customer or business value, for example, “improve on-site performance.”

“Evergreen lanes”

While planning roadmaps, we identified a few areas requiring monthly attention. The first is security updates, platform upgrades, and bug fixes. It’s important to allocate time and budget towards this area every
month. Generally, we recommend a 30/70 split between keeping the lights on work and roadmap development work, but this varies depending on the client and business needs.
The second lane we recommend planning for monthly is performance. Performance is impacted as more functionality gets added to websites and content is updated. We all know that conversion and performance
are interrelated—if performance is degraded, conversion is also negatively impacted.
The final lane is analytics and reporting. Similar to performance, as your website functionality grows, so does your need to measure and track data to understand its effects. We recommend keeping some
time and budget allocated towards improving data visibility and automated reporting, so you can actively track and monitor your data and progress.
The number of activities and projects behind each theme will determine the level of investment you will need in those areas. You need to allocate high-level budgets (in hours) towards each theme and ensure that you have a reasonable allocation of the budget towards the maintenance (upgrades, bug fixes, security updates) lane.
In summary, you should have a better idea of the total you invest towards each area by month and year. In addition, you will receive an overview of the division of work between roadmap development and bug fixes and maintenance.
A final note is to ensure you have identified your KPIs alongside your themes, according to what metrics the activities will impact.
This becomes important further down the line when you need to assess whether your efforts have had the right impact on your overall business goals.
Here’s a simplified example of what this roadmap plan could look like:

A thematic high-level plan


Do: Focus on what the customer sees

When it comes to User Experience and Performance, you need to focus on what customers are actually seeing. Too often, we focus on the look and the feel, but we don’t focus on the performance. Every millisecond longer your page takes to load is a great chance that that user will move on to your competitor’s site. Test for mobile speeds and slow connections. If you can get great perceived page speed there, the rest of your customers will have an amazing experience.

Don’t: overcomplicate frontend automation

Don’t spin your wheels, automating every portion of your frontend. Thirty percent of your site never changes, so make it static or control it via your CMS, not some tricky Javascript component. We see people developing highly complex navigation controls and code to run them when they realize that those menus change once a year. A better use of that effort could be put into killer search filtering controls and product visualizers that need complex logic.


05 A visual time-based roadmap

After constructing a visual roadmap, you will know where you are headed and how to get there without getting stuck. You need to communicate your plans effectively and visually without being tied to spreadsheets. Spreadsheets are great for organizing and prioritizing, but not for communicating a vision. Presentations take time to produce, and alignment is a continuous struggle in most organizations. A roadmap is a useful guide for teams and speaks to the long-term vision without losing sight of what is needed daily.

A note on themes

We have previously discussed themes and why they exist. When crafting the roadmap, it should be updated annually or quarterly to align with the current needs and objectives. Establishing these themes is a great way to gain buy-in and vision alignment from stakeholders and team members. Themes should be clear and actionable, so people are excited to implement them. While a vision is highly unlikely to change from year to year, themes can change quarterly or annually, as these create the foundation of your roadmap.

Plotting themes and planning

First, identify all of your key milestones. These include peak trading days such as Black Friday, the peak holiday season, and new campaign launches. Is there a particular feature or activity that needs to be completed by a certain time? Now is the time to indicate this, so you prioritize the right work and themes to support its success. An example is load testing and performance work leading up to Black Friday or an integration required for a lead form.
Once this is done, getting an idea of the capacity and budgets you need to work within will help prioritize the work you need to do. You want to ensure you have a good spread of efforts and hours across key themes but that your critical larger projects are accounted for in the months they need to be executed. Balancing the needs with your budgets and team capacity can be tricky, so keeping your roadmap flexible and easy to update is crucial.

Watch out

Keep close tabs on the time allocation for the bugs and maintenance lane and ensure that your roadmap is not impeded or eaten up by time spent on bug fixing. Ensure you can measure this regularly and report back to stay on track. A general rule of thumb is to split the allocated budget hours 70/30 between roadmap work and bugs. This ensures you always have hours for bug fixing, maintenance, and security. But it also provides significant hours to invest in your roadmap to achieve your goals and drive innovation.

Roadmap iteration frequency

Roadmaps are updated on varying frequencies, depending on organization size. Larger companies will update once every six months or annually, whereas smaller companies might choose to review quarterly. Flexibility is key, but long-term planning is needed when bigger teams are involved, and more dependencies are present.

What tools should you use?

Another consideration with whom you share the roadmap. You want to be able to view enough detail when discussing priorities with the teams, but you also want to get a high-level view when discussing with senior stakeholders. It is important to ensure that your tool can cater to these different views based on your company’s needs.


Do: Define and share your vision and prioritize flexibility

Nothing is worse than being blind to the expected results. A strategy is meant to reach company goals. And then, all the teams will embrace this strategy and adapt it to each of their channels, e.g., ecommerce websites, social shopping, marketplaces, distributors, and retailers. The more you share the vision and the goal with all the stakeholders, the more engagement and adoption with all the tools you’ll invest in you get!
Isn’t this the definition of a successful strategy roadmap?!
The key to building a sustainable digital roadmap is finding the balance between setting realistic, clear goals and allowing your organization to pivot and adopt new channels efficiently if needed.

Don’t: Neglect the employee experience

Choosing the right people in the organization to rally the troops and be true ambassadors will directly impact the customer experience you offer.
By allowing these ambassadors to work closely with your customers when building, managing, and communicating your digital roadmap, you can create a competitive advantage for your business.
It’s great and mandatory to be customer-centric, but never forget your employees, who will be the actors of the strategy!
By prioritizing the customer journey, you can make it easier for customers to find what they’re looking for on the right channel, make a purchase, and come back for more. This can result in higher conversion rates, increased customer lifetime value and loyalty, and improved overall business performance.


06 What makes a good digital roadmap?

We’ve covered everything from creating goals, identifying key performance indicators, and identifying activities and projects all the way through to building a high-level thematic plan and, ultimately, your visual roadmap.

A good digital roadmap should:
• Be easily shareable and understood
• Be easily updated and agile
• Provide transparency to the vision for all stakeholders
• Gain alignment and buy-in from team members
• Get the teams excited about what they are building and delivering

It’s now time to get started on your roadmap and start working towards your digital vision! If you need help or advice, reach out to our dedicated global consulting team, who can help guide and advise you on your journey.


Do: Communicate clearly and openly internally

It is essential to clearly articulate the strategy’s goals, objectives, and key performance indicators to all stakeholders, including executives, team members, and partners. Effective communication ensures everyone is aligned and understands the strategy’s vision, direction, and priorities.
Communication also helps to identify potential roadblocks and challenges early on and allows for collaborative problem-solving. Additionally, ongoing communication enables regular feedback and performance tracking, which is essential for adjusting and optimizing the strategy over time. Turn your strategic initiatives into everyday conversation topics and continually check — weekly if possible — to ensure success.
Exercise caution when communicating externally, as your strategies may change as the world and your place in it changes. Making changes is much more difficult if you’ve publicly communicated or promoted your strategic plan.
Remember that roadmaps seldom go exactly as planned, especially ones executed over an extended period of time. Embrace flexibility and be open to feedback and new ideas.

Don’t: Let fires and favors distract you from achieving your milestones

Fires are unexpected events or emergencies that require immediate attention, while favors are requests from colleagues or partners that may not align with your strategic goals and objectives. Allowing these distractions to take priority can result in a loss of momentum and a lack of progress toward achieving the digital strategy’s desired outcomes. You can achieve the desired outcomes efficiently and effectively by prioritizing and managing distractions carefully and balancing immediate needs with long-term goals and objectives.

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