[SURVEY RESULTS] The 2024 edition of State of Software Modernization market report is published!
GET IT here

Creating a Successful Digital Transformation Roadmap

Last updated on
July 15, 2024



Creating a Successful Digital Transformation Roadmap

Why a digital transformation roadmap is essential

A digital transformation roadmap serves as a strategic plan that outlines all the steps an organization must take to transition from its current state to a desired future. It helps businesses align technology with objectives, ensuring that each investment in tech supports the goals the organization strives to achieve. Moreover, it optimizes the entire digitization process by streamlining operations, increasing efficiency, and promoting productivity within teams responsible for software modernization.

A roadmap is also the best way to control budget and project scope. It provides clear direction and crucial milestones while allowing decision-makers to monitor and manage costs, as well as estimate potential timelines. Every company that wants to facilitate the development of new, modern products and services, should have a roadmap for digital transformation that showcases all the essential resources and activities to cover.

<span class="colorbox1" fs-test-element="box1"><p>Curious about some digital transformation examples? Learn how big players like Nike, Lego, Disney, Microsoft, and Audi approached digital transformation and succeeded.</p></span>

How to create a digital transformation roadmap

There are several points to check to prepare a roadmap that includes all requirements. Here’s our recommended list of stages to follow, with additional advice on how to execute them.

1. Assess current state

The whole process of creating a digital transformation roadmap should begin with the evaluation of your organization’s current digital maturity. This process should involve the assessment of the existing technology infrastructure and the determination of areas for improvement. Identifying outdated systems that require modernization and finding inefficiencies that block progress is crucial to prioritizing digitization goals. Every brand should focus on the operations that should be taken care of in the first place.


  • Conduct a comprehensive review of your current technology stack, including hardware, software, and network capabilities.
  • Identify gaps, outdated systems, and areas that hinder efficiency. Look for opportunities where technology can drive improvement.
  • Compare your digital maturity with industry best practices to understand where you stand.

2. Define vision and objectives

Establishing a clear vision for digital transformation efforts is the next phase. It should align with business goals and include specific, measurable objectives. For example, companies can focus on the following achievements:

  • Improving customer experience: Enhancing engagement and satisfaction through digital channels.
  • Increasing operational efficiency: Automating processes and reducing manual tasks.
  • Driving innovation: Developing new products or services using digital technologies.


  • Outline what you aim to achieve with digital transformation. This could be improving customer experience, enhancing operational efficiency, or innovating product offerings.
  • Ensure your digital transformation objectives align with the overall business strategy and long-term goals of the organization.

3. Identify key initiatives

Based on the vision and objectives determined in the previous step, the team should write down all the key initiatives that will drive the company’s digital transformation forward. These may include software modernization, cloud migration, introduction of advanced data analytics algorithms, AI integration, and more.

Legacy systems update might be one of the most important objectives - according to the State of Software Modernization 2024 Report, “(...) it is estimated that legacy systems cost businesses across the globe $2.6 trillion every year. 70% of IT budgets are consumed by this maintenance requirement alone”. This means that improving performance, scalability, and tech integration of outdated software should be imperative for all brands that still haven’t modernized.


  • Name critical operations that need immediate attention. These are often the areas that can provide the most significant impact when digitized.
    • Upgrade or replace legacy systems to improve performance, security, and integration capabilities.
    • Move applications and data to the cloud to enhance scalability, flexibility, and accessibility.
    • Implement advanced data analytics tools and techniques to derive actionable insights and drive data-driven decision-making.
    • Integrate AI and machine learning to automate processes, enhance customer experiences, and provide predictive insights.
    • Strengthen cybersecurity measures to protect against threats and ensure data privacy and compliance.
    • Develop mobile applications to meet the growing demand for mobile accessibility and enhance customer and employee engagement.

4. Prioritize initiatives

Not all initiatives can be tackled simultaneously. That’s why it’s crucial to pick the most pressing ones and handle them first. The prioritization can be based on various factors, including the impact on business goals, resource availability, dependencies, and technical competencies. Focusing on initiatives that deliver the highest value is usually the best strategy, but sometimes budget constraints or lack of skills can block some moves. Additionally, some parts of the digital transformation strategy must be completed before others can start.

The most mature organizations understand that a strategic digital framework is necessary to identify areas where they can take advantage of the benefits of digital transformation. - Dataversity


  • Develop criteria to rank the importance of different digitization projects. This can include factors like potential ROI, ease of implementation, and alignment with strategic goals.
  • Assess how each initiative aligns with and supports the company’s strategic objectives.
  • Consider the resources (financial, human, technical) required for each initiative and their availability.
  • Focus on initiatives that deliver the highest value to the business, whether through cost savings, revenue generation, or competitive advantage.
  • Assess the risks associated with each initiative and prioritize those with manageable risks and high potential benefits.

5. Develop a detailed plan

The overall roadmap should also be divided into more detailed parts, each with its dedicated plan that includes:

  • Scope and objectives: Clearly defined aim of each activity.
  • Timeline: Realistic deadlines and milestones set in time.
  • Budget: Estimated costs and appropriate resource allocation.
  • Risks and mitigations: Identified potential risks and strategies to mitigate them.


  • Develop a realistic timeline for implementing digital transformation initiatives. Break down the process into phases to manage progress effectively.
  • Designate teams or individuals responsible for each phase of the transformation. Ensure accountability and clear lines of communication.

6. Allocate budget

Digitial transformation process needs a budget. Conduct a thorough financial audit to understand your current financial position. Then, define the maximum budget that can be allocated without jeopardizing the organization’s financial health.


  • Divide each initiative into detailed components, such as hardware, software, services, training, and personnel costs.
  • Obtain quotes from vendors for hardware, software, and services. This includes licensing fees, subscription costs, and any potential custom development fees.
  • Calculate internal costs, including salaries, training programs, and any additional hiring required.
  • Allocate a contingency fund (usually around 10-20% of the total budget) to cover unforeseen expenses.
  • Consider a phased approach to spread costs over time, allowing for better financial management and adjustment based on the success of initial phases.

7. Identify risks

Understanding potential risks and having strategies in place to address them can help ensure the success of the transformation process.

Potential risks are:

Technical risks

  • Risks related to outdated technology failing during the transition.
  • Problems integrating new systems with existing infrastructure.
  • Risks of data breaches and cyber-attacks.

Operational risks

  • Disruption of business operations during the implementation of new systems.
  • Risks of system downtime affecting productivity and customer service.
  • Over-reliance on external vendors and partners.

Financial risks

  • Projects exceeding the allocated budget.
  • Uncertainty about achieving the expected ROI.
  • Insufficient funding for the entire duration of the transformation.

Human risks

  • Employees resisting new technologies and processes.
  • Lack of necessary skills and expertise within the team.
  • Key staff leaving during critical phases of the transformation.

Strategic risks

  • Initiatives that do not align with the overall business strategy.
  • Falling behind competitors if the transformation is delayed or unsuccessful.


  • Make a list of potential risks your team may encounter during digital transformation process.
  • Prepare a mitigation strategy for each of them.

8. Build a skilled team

Assembling a team with the necessary skills and expertise to execute a digital transformation strategy is a crucial step in every growth journey. Remember to include all activities that involve talent in your plan. Hiring new specialists who will be able to deliver the expected results might be required. However, outsourcing is an option to strongly consider - leveraging external partners can be the best way to optimize resources and get spectacular quality.

For example, working with developers from cost-effective regions like Poland is the best way to get a high level of technical expertise at a competitive price. A trusted outsourcing partner can play a pivotal role in any digital transformation. Instead of spending money and time on finding suitable experts, you get access to a large talent pool of IT professionals who can quickly fill skill gaps in your team. Lower labor costs compared to Western Europe and the USA mean significant savings and budget control. Additionally, outsourcing is a more flexible method of scaling dev teams and speeding up the production processes, which accelerates time-to-market.


  • Determine the specific skills and expertise needed for your digital transformation initiatives, such as software development, data analytics, cybersecurity, project management, and digital marketing.
  • Evaluate the existing talent within your organization to identify skill gaps and areas where additional expertise is needed.
  • Recruit or appoint internal experts in key areas such as cloud computing, AI, machine learning, data science, and cybersecurity.
  • Research and select reliable external partners or vendors with a proven track record in delivering high-quality digital transformation services.
  • R

<span class="colorbox1" fs-test-element="box1"><p>Since you may need some help, here's a ranking of top digital transformation companies. You may also want to check top legacy app modernization companies.</p></span>

9. Implement change management

Successful digital transformation requires effective change management to ensure that involved stakeholders embrace new technologies and processes. Fostering open, honest communication and informing all interested parties about the progress is imperative to stay on the same page and address the challenges of each group. Training and adaptation support can also help teams thrive, so involving them in the roadmap is essential. Finally, creating channels to exchange feedback, discuss important matters, and address concerns promptly is the best way to execute digital transformation and achieve assumed goals.


  • Include professionals who can manage organizational change, ensuring smooth transitions and employee buy-in.
  • Develop a comprehensive communication strategy to keep all stakeholders informed about the transformation progress, goals, and benefits.

10. Optimize software delivery

A key aspect of the digital transformation roadmap is to find the most optimal way to deliver robust software. There are several ways to do it. For example, working with providers that work with agile methodologies (at Brainhub, we use a Prince2Agile approach) increases flexibility and adaptation, improves collaboration, and supports teams in providing value in each iteration. Integrating DevOps practices supports automated software release processes for better reliability, proactivity, and continuous delivery.


  • Opt for agile methodologies, such as Scrum or Kanban, to enhance flexibility and adaptability. For example, the Prince2Agile approach can be used to combine the control of Prince2 with the flexibility of agile.
  • Focus on iterative development to deliver value in small, manageable increments. This allows for regular feedback and continuous improvement.
  • Form cross-functional teams that include developers, testers, and business analysts to improve collaboration and communication.
  • Implement DevOps practices.
  • Focus on Quality Assurance and security best practices.
  • Track key metrics, such as deployment frequency, lead time for changes, mean time to recovery (MTTR), and change failure rate, to measure the effectiveness of your software delivery process.

11. Monitor and adjust

Digital transformation is an ongoing process. Continuous progress monitoring against the roadmap is more than welcome, but the team should also be prepared to make adjustments as needed. Conducting periodic reviews to assess the performance of software systems allows organizations to achieve true excellence. it’s also encouraged to watch metrics and KPIs - this way, everyone can be aware of achieved milestones and areas that require improvement.


  • Establish continuous monitoring framework.
  • Implement monitoring tools.
  • Gather and analyze feedback.
  • Analyze the collected data to identify trends, bottlenecks, and opportunities for enhancement.
  • Based on the analysis, prioritize adjustments that will have the most significant impact on achieving your digital transformation goals.


Creating a roadmap for digital transformation is a critical step towards software modernization and overall business improvement. It’s crucial when strategizing the whole process - it should be done with attention to detail and solid preparations. This way, organizations can predict potential challenges and minimize their negative impact. This allows them to focus on what matters and ensure their customers, employees, and partners experience spectacular results.

By following the steps outlined in this guide, you can develop a clear and actionable plan that aligns with your business goals. Leveraging the advantages of technology while also working with seasoned, established outsourcing partners can further enhance your transformation efforts, ensuring faster, better, and more controlled outcomes. Embrace the future of digital transformation and drive your organization towards sustained success and innovation.

Frequently Asked Questions

No items found.

Our promise

Every year, Brainhub helps 750,000+ founders, leaders and software engineers make smart tech decisions. We earn that trust by openly sharing our insights based on practical software engineering experience.


Olga Gierszal
IT Outsourcing Market Analyst & Software Engineering Editor

Software development enthusiast with 7 years of professional experience in the tech industry. Experienced in outsourcing market analysis, with a special focus on nearshoring. In the meantime, our expert in explaining tech, business, and digital topics in an accessible way. Writer and translator after hours.

Leszek Knoll
CEO (Chief Engineering Officer)

With over 12 years of professional experience in the tech industry. Technology passionate, geek, and the co-founder of Brainhub. Combines his tech expertise with business knowledge.

Olga Gierszal
IT Outsourcing Market Analyst & Software Engineering Editor

Software development enthusiast with 7 years of professional experience in the tech industry. Experienced in outsourcing market analysis, with a special focus on nearshoring. In the meantime, our expert in explaining tech, business, and digital topics in an accessible way. Writer and translator after hours.

Leszek Knoll
CEO (Chief Engineering Officer)

With over 12 years of professional experience in the tech industry. Technology passionate, geek, and the co-founder of Brainhub. Combines his tech expertise with business knowledge.

Read next

No items found...

Get smarter in engineering and leadership in less than 60 seconds.

Join 300+ founders and engineering leaders, and get a weekly newsletter that takes our CEO 5-6 hours to prepare.

Thank you! Your submission has been received!
Oops! Something went wrong while submitting the form.

previous article in this collection

It's the first one.

next article in this collection

It's the last one.