How a Finance Team Started Transforming Their Work Through Digital Change

In this edition, I’m taking digital transformation from abstract discussion to concrete success and sharing a real story.  I had the privilege of working alongside a small but determined finance team that took a leap, embraced change, and delivered results beyond expectations. Here’s how it happened.

Undervalued, Under-Resourced—and Ready to Change

As a department, we were one of the smallest in the organization. To many of you reading this newsletter, the reason will be all too painfully familiar. Finance and accounting are still widely considered back-office functions—overhead that must be minimized. But we know that’s not what we are.

We’re a critical department that holds the answers to every question about the business. From ROI to cash flow to program effectiveness, finance has the insights. Yet we were drowning in manual processes—reconciliations, expense tracking, scattered systems—and it was costing the business both visibility and agility. In this environment it was difficult to make the case for our value when we were just trying to survive from one month-end close to the next.

Meanwhile, the organization was moving ahead rapidly: new programs, new pricing structures, new products and markets. But no one knew whether those efforts were paying off. There were no KPIs, no customer segmentation, no post-mortem analyses—just spending without insight. Then came the unexpected rise in inflation, surplus turned into deficit, and the cracks in the foundation deepened.

Looking at this and knowing exactly how we can help, we decided that this could not continue much longer. We knew something had to change—and finance decided to lead the way.

Bold Take: You can’t drive a growth strategy with a broken dashboard—finance must modernize or risk becoming irrelevant.

Breaking Down the Silos: Why We Mapped Before We Moved

Finance wasn’t the only department that needed to level up its digital systems game. The entire organization needed to shed its disconnected, siloed tech setup in favor of flexible, modern infrastructure. Step one was to enlist the help of others.

Before launching our digital transformation, we partnered with stakeholders across the organization to understand their needs and pain points. Their input shaped two key insights:

1. Our issues were deeper than we thought.

2. We needed a scalable system that could connect to future tools.

   
   

Working closely with our colleagues, we created side-by-side diagrams of our current and future states. These visuals clearly exposed capability gaps and system limitations. Alongside them, we documented the must-have features that  would solve current problems and elevate our analytical capabilities.

With this foundational work in place, another thing became clear: the finance transformation would need to proceed separately from the broader organizational overhaul. Why? Because we could move faster. We could implement a new financial system before the organization could complete its full transformation, lead the way and bring back lessons learned.

This fork in the road was both a challenge and an opportunity. Our system would need to integrate into the larger ecosystem later, but in the meantime, we had no idea what that ecosystem would look like. This was our challenge while the opportunity was in showcasing the results digital transformation can deliver.  So, we decided to add a risk management layer into our process and move  forward.

Bold Take: Don’t wait for the whole company to transform—finance can (and should) lead with a clear, connected plan.

The Must-Haves That Shaped Our System

From the start, we knew we’d be moving ahead of the rest of the organization. That gave us a head start in improving our own processes. But it also introduced risk: we didn’t know what systems or platforms the rest of the organization would choose, or what their technical requirements might be. In order to future-proof our work, we prioritized flexibility and scalability.

Our first non-negotiable? A financial platform with robust open APIs to enable integrations with other platforms.

Second, we needed intuitive reporting tools. Stakeholders had been asking for years to access their own data in real time—and many of them were tech-savvy enough to know it shouldn’t be that hard. We also knew that our ability to turn fiscal results into actionable insights had long been lacking. We needed user-friendly, ad hoc reporting capabilities that would support faster, smarter decision-making.

Third, we focused on automation. Manual reconciliations, offline storage, and limited, stale reporting were dragging us down. Instead, we wanted workflows that automated reconciliations, allowed document storage in transaction records,  supported drill-down capabilities, and gave our team the space to shift from transactional tasks to strategic analysis. This was our chance to grow professionally while helping the organization scale operationally.

Now we had our three core areas of focus —external stakeholder needs, internal team priorities, and organizational goals—to build a system that was scalable, flexible, and responsive. To this we added a detailed requirements list with specific finance needs: auto-matching, expense imports, AP integrations, and other key processes.

With our list in hand, we began interviewing vendors. Each team member rated vendors on each requirement, and we debriefed after each meeting. One by one, we narrowed the list until we landed on the platform that fit.

Bold Take: A successful system isn’t just about features—it’s about aligning tools to your people, processes, and future goals.

Building the Plane While Flying It

The months that followed tested our bandwidth. Implementation meant doing two jobs: running the business while rebuilding it. There were no extra hires or deadline extensions. The month-end still had to close on time. Board reports still had to go out. Payroll issues still had to be resolved. And, of course, the unexpected always showed up.

In early conversations with our consultants, we laid out our issues transparently and made the case for our intended end result.  The more we talked, the clearer it became clear that we needed to rebuild how we recorded transactions and captured data. That meant rethinking our chart of accounts, deciding how to segment data, and determining how to store it for maximum flexibility.

Should a variable be a GL account or a new data segment? Would it be used in combination with other variables? If so, how would that affect our ability to “slice and dice” data in reporting? We had to ramp up fast—and yes, we were building the plane while flying it.

Here’s one example. As we created new data segments (tags that enable “slice and dice” reporting), we aimed to make them user-friendly. So, we created plain-language descriptors to enable users to easily tag transactions. Then, we uploaded several years of historical data and tagged everything accordingly.

After all this work was done came a major learning moment—from a casual conversation with IT. Those user-friendly descriptors? Too long for effective API use. Our decision had created a roadblock for system integration. 

Because having a future-proof finance platform was a core focus area for us, we had to fix this issue. So, we discussed the best API format for those dimensions, re-created the tags in the system and then spent four weekends retagging data. It was frustrating—but valuable. The takeaway for us was of paramount importance. You must align user needs with technical specs—and transformation only succeeds when every expert has a seat at the table.

Bold Take: If you’re not talking to everyone, you’re not ready to transform—real change requires full-spectrum collaboration.

Delivering Early Wins to Build Trust

Showcasing the value of digital transformation was always our priority. Even as we made progress, skepticism lingered in the organization. Was it really worth the investment?

We knew an early win could build momentum. So as soon as our first data set was loaded, we started experimenting with dashboards that could be pushed out to end users. While the interface was intuitive, we hit some snags—missing data, grouping issues, inconsistent visuals. It took an investment of time and effort to customize data displays to match real-world needs and to iteratively run dashboard mock-ups until we landed on the format that worked.

But once we worked through the kinks, we had something powerful: interactive dashboards that let users explore their own data, in real time.

We prefaced the demo with “this is a work in progress.” But the impact was undeniable. Seeing data live, flexible, and in their own hands changed the perception of what finance could deliver.

Bold Take: Transformation wins support when people can see and feel the results for themselves.

From Reactive to Strategic: The End Result

We were short on time, money, and people—but that didn’t stop us from building a game-changing digital finance platform.

Patience and intention guided our process. We mapped current processes to future outcomes, identified gaps, and created solutions. We acknowledged what was out of our control—and planned accordingly. We prioritized both team and stakeholder needs throughout.

We didn’t rush. We implemented thoughtfully, not hastily. When issues arose, we paused, assessed, and corrected. 

In the end the digital transformation project ended up being the first step toward transforming the standing of our department from back office to strategic partner. We learned through real sweat equity what it takes to enable change of this scale and impact. Lessons learned and successes gained here paved the way for personal and organization growth that would not be possible otherwise.

Bold Take: Digital transformation isn’t just a system upgrade—it’s a mindset shift that redefines your role in the business.