Getting Digital Transformation Right: Opportunities in the Moment

Key Takeaways

• Digital transformation has shifted from survival to strategy, requiring organizations to align technology adoption with long-term business goals and cultural evolution.
• Success depends on factors like artificial intelligence (AI) literacy, cloud adoption and workforce training.
• Culture is as critical as technology. Trust, transparency and continuous learning are essential for building an AI-ready organization.
• Scalable, modular technology and solutions enable middle market firms to compete effectively.

Why digital transformation matters

Five years ago, the term "new normal" represented the urgency and improvisation of a world propelled into digital acceleration. As organizations across all sectors were abruptly forced to take their operations online, examples of ad-hoc digital transformation appeared everywhere: Hospitals and physician practices started to increase their use of telemedicine to serve patients; restaurants partnered with delivery apps like GrubHub and DoorDash to help their businesses stay afloat; and financial institutions saw an exponential increase in the use of their digital products.

Today, however, digital transformation is more than a survival tactic—it’s a strategic imperative rooted in cultural evolution and the ability to differentiate and lead in a digitally driven marketplace. As artificial intelligence (AI), cloud-native platforms and data-fueled innovation become central to how businesses operate, executives are redefining how their organizations function and deliver value in a rapidly evolving digital economy.

To keep pace with today’s environment, organizations are leveraging both culture-driven innovation and emerging technologies to ensure transformation efforts are sustainable and aligned with long-term business goals. Here’s what to know when curating a digital transformation strategy.

Digital transformation for businesses and workforces

A workforce that understands digital transformation trends, how new technologies work and how they can be applied to achieve business objectives is key to successful digital transformation. For AI specifically, Microsoft’s 2025 research highlights the critical nature of training when it comes to using the tool to its full potential. Within organizations that have enterprise-wide data and AI literacy programs, 90% report faster decision making, 81% report increased revenue and 81% report better employee retention.

SHRM’s data further emphasizes this point, sharing that 77% of respondents said AI allows them to accomplish tasks faster and 73% reported improvements in work quality. This affirmative response, however, is most evident in organizations invested in upskilling and training their workforce.

Despite these gains, many companies still face a critical gap in equipping their employees with the skills to use AI effectively. In fact, 62% of leaders report their organization has a discrepancy in skills when it comes to AI literacy. This disparity underscores a dire need for companies to invest in structured training opportunities, allocate time and resources for employee development and foster a culture of continuous learning and technological adaptability.

For middle market companies, digital transformation does not require enterprise-level budgets to be effective. Scalable solutions, such as modular AI tools, cloud-based platforms with flexible pricing and open-training resources, can help organizations build digital fluency without overextending budgets. Partnering with vendors that offer tailored onboarding and support can also boost adoption while minimizing disruption.

If all this sounds daunting, and you’re unsure of how to start building a digitally fluent workforce that feels empowered to embrace new technology like artificial intelligence, you can begin by asking the following foundational questions:

• Does my workforce understand the tool?
• What will training and support look like for our teams?
• How will we measure the tool’s performance and outcomes?

Your answers to those questions can guide your first steps toward building a digital workforce that’s equipped to not just adopt new technologies, but to drive meaningful transformation through them.

Fostering a culture for digital transformation

While equipping employees with the right technical skills is critical, it’s only one part of the equation. Successful digital transformation also demands a culture that embraces change, encourages innovation and aligns technology adoption with organizational values and long-term strategy.

Consulting firm Deloitte shares that a culture grounded in trust, data fluency, agility and change management is essential to successfully adopting transformative technologies like artificial intelligence. In an interview with the Deloitte and CDO Magazine, Eileen Vidrine, chief data officer at the US Department of Air Force shares that "It’s really about working together, building collaborative, trusted partnerships. In organizations where that may be lacking, it’s imperative to support trust-and relationship-building to break down silos."

Charlene Li, founder and CEO of Quantam Network’s Group also spoke to the importance of transparency and accountability at SHRM’s The AI+HI Project in San Francisco, sharing that "transparency involves a commitment to continuous monitoring, ethical practices and clear communication about AI’s capabilities and limitations. It includes disclosing how and when AI will be used, especially for decisions that impact people."

She further expands on this by sharing what she believes to be the "Five Beliefs That Define AI-Ready Cultures" in a recent article on LinkedIn:

• Speed over perfection
• Focused experimentation
• Questioning Assumptions
• Continuous Learning
• Shared Purpose

These points emphasize that developing an AI-ready culture is about more than just technology. Organizations that prioritize trust, transparency and shared purpose are better equipped to unlock the full potential of digital transformation.

By fostering collaboration, encouraging experimentation and embracing continuous learning, leaders can build resilient cultures that adapt quickly to change and sustain long-term growth in a rapidly evolving digital landscapes.

Mastering the technology part of digital transformation

In 2025, middle market companies are no longer cautiously experimenting with digital tools; they’re strategically investing in technologies that drive efficiency. Forbes reports that the most impactful returns are coming from both AI-led decision making and backend operations like predictive maintenance, customer support and automation.

On top of AI, cloud computing remains a foundational part of this revolution. Scalable cloud platforms are allowing middle market companies to access enterprise-grade capabilities like real-time collaboration, secure data storage and advanced analytics without the overhead of legacy infrastructure.

These technologies are not just operational upgrades; they’re strategic assets that help middle market firms compete with larger organizations. By implementing solutions that are modular and scalable, companies can accelerate innovation without overextending resources.

Ultimately, mastering technology means investing in tools that empower people, streamline processes and position the organization for long-term success in a digital-first economy.

AI-driven transformation: The future is already digital

Digital transformation is no longer a trend; it’s the foundation of how organizations operate, compete and grow. The shift to cloud-based platforms, AI-powered tools and hybrid work models has become permanent, with companies increasingly integrating digital capabilities into every part of their operations.

Middle market organizations that invest in digitally savvy talent, foster a culture of innovation and approach technology strategically will be best positioned to thrive. As digital maturity continues to serve as a key differentiator, leaders must ensure their teams are equipped to drive transformation through these new tools.

Contact your relationship manager to learn more about how your organization can take the next step.