How Middle Market CFOs Can Overcome Modern Operational Barriers

A comprehensive approach to modernization   

With the continued emergence of AI and automation, middle-market organizations are faced with several questions, the answers to which can create a competitive advantage for organizations in a highly competitive market: How do I stay up to date with technology trends and improve how my organization operates?  How do we effectively allocate resources and capital to invest in the right solutions that will create value in my organization?  Where do I start and how do I prioritize opportunities within my organization to drive the most operational efficiencies?   Middle-market CFOs are evaluating these questions every day, and the answers to these questions can have a profound impact on organizational performance.

On paper, these opportunities promise efficiency, improved processes and significant ROI. However, in practice, many middle-market finance organizations struggle to effectively achieve a targeted ROI from many of these investments. This gap highlights why the modernization of the middle market finance organization must be approached as a continuous, integrated effort; one that aligns people, processes, data, and technology to create lasting operational agility, strategic impact, and achieve the targeted value creation goals.

People First: The Cornerstone of Modernization   

Technology alone cannot drive transformation; success depends on equipping teams with the skills and mindset to interpret data, optimize workflows, and lead strategic initiatives. Automation can eliminate manual tasks and free up time, but the real value comes when finance teams use that time to support the organization in driving strategy and being a key partner in creating value for the organization.

Several key areas where middle market finance teams can drive value: using data to be more predictive – understanding historical trends and readily available market data to model what is going to happen, versus what has already happened; utilizing data to build dynamic plans – helping the organization respond to market dynamics and taking advantage of opportunities in the market through dynamic planning; supporting the business with data that allows sales and operations to make the appropriate adjustments to improve organizational performance.  This requires upskilling of finance team members, and is not a “traditional” finance organization – it is a modern finance organization, one that supports and drives strategy and creates enterprise value.

A Foundation for Finance to Thrive 

True modernization redefines the finance function, from a transactional back-office role to a forward-looking strategic partner, by streamlining operations and enabling insight-driven decision-making. This shift is enabled by streamlining operations and embedding insight-driven decision-making into daily workflows.

By automating core processes such as reconciliations, accounts payable, and receivable, finance teams can eliminate inefficiencies and reclaim time for higher-value activities. These efficiencies enable teams to move from reactive reporting to proactive planning—focusing on forecasting, scenario modeling, and strategic advising.

Importantly, the value created through these efforts doesn’t just improve operations; it fuels growth, enhances profitability, and lays the foundation for continued modernization. As finance becomes more agile, its ability to anticipate change and guide strategic decisions becomes a defining advantage.

From Data to Insight 

Fragmented systems often leave CFOs with incomplete views of performance. By unifying data platforms and standardizing inputs, finance teams can ensure accuracy and trust in the numbers. This shift allows finance to move from explaining what happened to anticipating what’s next. Moreover, strong data enables teams to implement dynamic planning—to be nimble enough to continuously plan and stay ahead of emerging issues, and to prepare for all possible scenarios.

The differentiating factor that many CFOs fail to understand is that modernization is a holistic exercise in operational improvements, not simply procuring the latest technology stack. Technology is the accelerator, not the driver. Tools like ERP systems, AI forecasting, and advanced analytics enable faster reporting, deeper insights, and greater situational awareness, but only when combined with strategic improvements to:

1. People: Teams must be equipped with the skills and confidence to use new tools effectively. This includes understanding how to interpret outputs, apply insights, and contribute to strategic decision-making.
2. Processes: Finance workflows should be optimized to support scalability, accuracy, and agility. Streamlined operations reduce manual effort and create space for forward-looking analysis.
3. Data: Clean, unified data is foundational, but its value is only realized when paired with strong data literacy. Finance teams should be able to manipulate data, model scenarios, and build forecasts that inform decisions. This enables a shift from reactive reporting to proactive insight generation.

CFOs who see modernization as a journey rather than a one-time project unlock operational agility and ensure that new tools are leveraged to their full potential.

Three Skills to Unlock Modernization 

Three core competencies stand out as critical areas for development and often act as barriers to modernization, especially for small and medium-sized businesses.

1. Digital Confidence: Finance teams must build confidence in using digital platforms, automating workflows, and extracting actionable insights from technology. Equally important is data literacy. Teams should be equipped to be able to read, understand and communicate data effectively once new technology is introduced.
2. Data Literacy: Organizations can support this by offering workshops on analytics and visualization, while ensuring access to clean, standardized data.
3. Strategic Thinking: Finance professionals need to evolve from reporting what happened to anticipating what’s next. Scenario-planning exercises, cross-functional projects, and mentoring programs can help cultivate a forward-looking mindset that positions finance as a strategic partner in driving growth and resilience.

Together, these skills form the foundation of a modern finance function that is agile, insight-driven, and prepared to lead in a rapidly changing business environment.

Finding the Right External Partner 

Finance modernization is a complex process that touches every part of an organization, from systems and workflows to talent and decision-making. For many CFOs, engaging external expertise early can make the difference between a smooth transformation and one marked with delays and misalignment.

The right advisor brings more than technical know-how; they offer a cross-industry perspective, help identify risks before they escalate, and guide strategic decisions with objectivity and clarity. Their involvement can accelerate progress and ensure that modernization efforts remain focused on long-term value.

Selecting an external advisor should be a strategic decision, not a final step once the roadmap is written. CFOs benefit most when they engage support at the outset, allowing for consistent guidance throughout the planning and execution process. This continuity helps maintain alignment with business goals, challenges are addressed as they arise, and momentum is maintained across every stage of the journey.

Modernization Only Succeeds With Cross-Functional Collaboration 

Successful modernization depends on cross-functional collaboration and alignment with the organization’s fundamental priorities. The key is to connect the goals of cross-functional teams with the unique needs and goals of your organization. Using a tailored and holistic approach that addresses people, processes, data, and technology simultaneously and in relation to one another enables finance teams to become more agile, forward-looking, and competitively distinct.

While the right data and technology are essential for accelerating transformation, the implementation process is equally vital. A thoughtful approach to execution supports long-term viability and helps embed change across the organization.

External advisors can play a pivotal role in this journey. When engaged early and intentionally, they do more than advise; they help execute, sustain momentum, and embed new capabilities. As more CFOs signal that modernization efforts are planned or already underway, the quality of the transformation and the end capabilities of a finance team will become a distinct characteristic in the marketplace.

Written by Dan Wheadon.