Isaac Sacolick
Contributing writer

3 key roles for driving digital success

Aug 22, 20237 mins
Digital TransformationIT LeadershipStaff Management

The capacity to transform digitally needs to be a core organizational competency, and it requires creating a team of digital trailblazers to pave the way to continuous improvement.

Business people in office having conversation and using technology.
Credit: Shutterstock / Liderina

If digital transformation is a journey, when does it end?

This is a question I am asked often by IT leaders who prefer slowing down the pace of transformation and technology innovation. Others who believe the term digital transformation is watered down take a more cynical tack, viewing it as a phrase leaders use to garner support for technology investments and vendors use to sell their newest capabilities.

But digital transformation remains a vital endeavor for today’s enterprise as it is about evolving the business and operating model and not just about modernizing technologies.

It is driven by changes in customer expectations, opportunities to evolve employee experiences, and building differentiating capabilities with data, analytics, and artificial intelligence — all of which have no clear end point, nor are exclusively technology-focused. As such, organizations must evolve their digital strategies with market changes, such as the shift to remote work in 2020, the evolution to hyperautomation in 2022, and how generative AI will now require CIOs to overhaul their roadmaps.

“You will always be transforming, and organizations must drive digital transformation as a core organizational competency,” I wrote in Digital Trailblazer.

To do so, CIOs must close execution gaps in their digital transformation strategies, as execution too often lags behind intention, with only 35% of board directors believing that their organizations are on track to delivering digital transformation objectives. Another study of 4,000 global organizations found that only 44% had a high digital maturity.

To help close this digital maturity gap and drive digital transformation as a core competency, CIOs and their leadership colleagues must establish and enlist digital transformation leaders across the enterprise. These digital trailblazers, as I call them, are vital for digital transformation success, as they can be delegated leadership responsibilities such as the planning, execution, and change management of your digital initiatives.

After all, evolving the organization’s culture, processes, and technology practices is something the CIO can’t do alone.

Product and delivery leaders: Agents of change

While there are many ways to charter a program and define leadership responsibilities, I recommend leading transformation initiatives with these two key roles.

The product leader, sometimes called product manager or product owner, ensures that a transformative initiative is strategic and customer-driven. Initiatives that prioritize wish lists from high-ranking stakeholders or ones that express requirements as solutions fail this test.

Product leaders must define a vision statement, research end-user needs, and propose roadmaps. They must collaborate with execution teams on an agile process that adopts continuous planning, delivery, and transformation practices and seeks customer feedback to adjust priorities.  

Product leaders are most responsible for a digital transformation initiative’s scope, priorities, and change management. They partner with agile delivery leaders responsible for delivering releases on time and meeting quality standards, including non-functional security, performance, and reliability acceptance criteria.

Product leaders define the opportunity and problem statement, while delivery leaders establish the solution’s architecture, execution plan, and support model. There’s a tension between the product leader’s goal of delivering more capabilities faster and the delivery leader’s quality responsibilities that extend into operations. 

Domain experts: Specialized standards bearers

Product and delivery leaders guide self-organizing, multidisciplinary agile teams to deliver reliable releases, capture end-user feedback, and demonstrate business impacts. The agile methodologies and tools differ by organization and sometimes by team, but what team leaders really want is the autonomy to make quick decisions around priorities, solutions, and technologies.

Therein lies a tradeoff for CIOs, product leaders, and delivery leaders. Provide teams with too much autonomy, and they may not have the knowledge and skills to implement or make optimal decisions. Even when they do, the aggregate of multiple teams making independent decisions can result in significant technical debt and high costs in maintaining a hodgepodge of platforms and implementations. 

On the other hand, creating bureaucratic processes and rigid standards slows and demoralizes teams. Few technical leads want to create and present a ten-page deck to an architecture review board, and teams automating their releases with CI/CD and other devops automations are slowed down if they must review releases with a change approval board.

To address these gaps, product and delivery leaders must rely on domain experts, including solutions architects, user experience (UX) specialists, Six Sigma analysts, information security leaders, and data architects. Most organizations can’t afford to staff domain experts with active roles on agile teams, so they consult with teams on their requirements and solutions.

More importantly, CIOs should challenge their domain experts to propose, define, communicate, and evolve self-organizing standards. These are bottom-up standards crafted in partnership with agile teams, have applicability to how other teams operate, and ensure that best practices continuously evolve.

It’s these self-organizing standards that help organizations build digital transformation core competencies. Examples include:

  • User experience specialists provide team brand, design, information architecture, and style guides.
  • Six Sigma specialists interview end-users, document existing business processes, and guide teams on what business workflow areas benefit from automation, tooling, and other modernization efforts. 
  • Solutions architects create standardized stacks, microservices, and reusable patterns.
  • Information security specialists guide agile teams on shift-left security practices.
  • Data architects, who partner with data scientists and data governance specialists, ensure new data sources are cataloged, comply with enterprise naming conventions, and adhere to data security requirements.  

CIOs should meet with domain experts regularly, and a best practice is to establish KPIs demonstrating the adoption and value delivered by self-organizing standards.

Agile PMOs: Connecting execution with digital strategy

CIOs must also present to their leadership teams and board directors the status of their digital transformation initiatives, the financial impacts, and roadmap changes. For larger enterprises with multiple running initiatives, relying on product and delivery leaders to perform consistent reporting can be time-consuming and distracting.

CIOs should look to revitalize their program management offices (PMOs) from top-down compliance drivers to bottom-up service providers. It’s a similar and not-easy transition program to how program and project managers had to learn when transforming from waterfall to agile methodologies.

Agile PMOs close the loop on digital transformation as a core competency through several activities. CIOs can tap PMOs to communicate compliance requirements, drive learning objectives, and promote hiring practices that meet diversity objectives. When working with teams, they should simplify vendor management and reporting, including financial and other KPIs. Agile PMOs take on these responsibilities and reduce the frictions that slow teams down.

Digital transformation isn’t dead — it’s becoming table stakes. Boards and business leaders expect CIOs to continuously guide and deliver competitive technology and data capabilities. What teams delivered last year is old news and will require ongoing modernization. Digital transformation as a core organization competency is an evolution of the IT delivery model, and creating a team of digital trailblazers paves the way for delivering innovation and continuous improvement.

Isaac Sacolick
Contributing writer

Isaac Sacolick, President of StarCIO, a digital transformation learning company, guides leaders on adopting the practices needed to lead transformational change in their organizations. He is the author of Digital Trailblazer and the Amazon bestseller Driving Digital and speaks about agile planning, devops, data science, product management, and other digital transformation best practices. Sacolick is a recognized top social CIO, a digital transformation influencer, and has over 900 articles published at InfoWorld,, his blog Social, Agile, and Transformation, and other sites.

The opinions expressed in this blog are those of Isaac Sacolick and do not necessarily represent those of IDG Communications, Inc., its parent, subsidiary or affiliated companies.

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