Building a Finance Foundation for the Next Stage of Growth

When Connor O'Leary joined Highway as Director of FP&A, he wasn't looking to improve a reporting process.

He was looking to modernize the company's finance infrastructure.

Highway, the leading provider of Carrier Identity® solutions for freight brokers,  was scaling quickly. The platform helps brokers verify carrier identity, reduce fraud, and book freight with confidence. Revenue and headcount were growing year over year, investor expectations were increasing, and finance was still operating primarily through QuickBooks and Excel.

Before Connor joined, the company had a small accounting team and a CFO, but no dedicated FP&A function.

As Highway entered its next phase of growth, it became clear that the finance stack needed to evolve alongside the business.

"We weren't equipped with the data to be strategic," Connor said. "It would require a ton of headaches and manual workarounds to get to that level."

The Challenge: Disconnected Systems and Manual Processes

Like many high-growth companies, Highway started with a simple finance setup.

QuickBooks handled accounting. Excel handled planning, forecasting, and reporting.

The process worked, but it was highly manual.

Data was exported from QuickBooks, manipulated in spreadsheets, and rolled into reporting packages. Product-level revenue visibility was limited. Forecasting relied on offline models. Understanding the drivers behind business performance often required significant manual work.

"We didn't have any insight into what was happening until the end of the month," Connor said.

"If we wanted to get into the weeds, we had to dive back into transaction-level detail manually."

The finance team knew where the business stood.

What they lacked was the ability to quickly understand why.

As the company continued growing, Connor knew the existing approach would eventually become a bottleneck.

A Finance Leader Who Had Been Through It Before

This wasn't Connor's first finance transformation. Before joining Highway, he had led multiple finance software evaluations and implementations, including deployments of Planful and Adaptive.

Those experiences shaped what he wanted and, just as importantly, what he wanted to avoid.

"I've done this a few times," Connor said.

As he began evaluating technology for Highway, flexibility quickly became one of the most important criteria.

The company was evolving rapidly, new products were being introduced, organizational structures were changing and reporting requirements were becoming more sophisticated.

Connor needed systems that could adapt alongside the business.

"We're still a young company," he said. "Products get added. Structures change. We need something that can move with us."

His previous experience with more traditional finance systems taught him that making changes after implementation often became difficult, expensive, or required significant workarounds.

This time, he wanted a different approach.

Evaluating a New Approach to Finance Technology

As Highway rebuilt its finance infrastructure, the team evaluated both traditional and modern approaches to accounting, ERP, and FP&A.

For Connor, the goal wasn't simply replacing spreadsheets.

It was creating a connected finance ecosystem that would allow a lean team to scale efficiently.

The evaluation criteria were straightforward:

• Flexibility as the business evolves

• Ease of implementation

• Strong integrations across the finance stack

• Scalability without adding unnecessary complexity

• Technology that could be managed by a lean team

"I knew kind of what I wanted when I came in here," Connor said.

Having gone through multiple software evaluations in previous roles, he already had a strong point of view on what would work for Highway's stage of growth.

Ultimately, that search led the team to Rillet and Abacum.

Building a Connected Finance Stack

Over the course of the next year, Highway transformed its finance infrastructure.

The company implemented:

• Rillet as its accounting and ERP foundation

• Abacum as its FP&A platform

• Stripe for billing workflows

• Ramp for spend management

• Salesforce as its commercial system of record

Rather than viewing these as individual technology purchases, Highway approached the initiative as a broader finance transformation.

The goal was to create a connected system where data flowed automatically between platforms and finance could spend less time gathering information and more time analyzing it.

"The last 11 months have just been continuous change across the organization," Connor said.

"We're working toward a best in class tech stack."

Why Highway Chose Rillet and Abacum

For Highway, the decision ultimately came down to flexibility, usability, and partnership.

On the accounting side, Rillet provided a flexible foundation that aligned with the company's growth stage and broader vision for its finance stack.

On the FP&A side, Abacum stood out for both the product and the people behind it.

As Connor put it, "We need something that's open-ended."

The implementation experience also played an important role in the decision.

Connor valued having continuity throughout the process, from evaluation through implementation, and appreciated working closely with a team that understood Highway's goals from day one.

"I felt most comfortable with the team," he said.

That combination of flexibility, partnership, and long-term scalability made both platforms a natural fit.

From Disconnected Spreadsheets to a Connected Workflow

Today, Highway operates with a connected finance stack.

Salesforce opportunities flow into Rillet.

Rillet manages invoicing, billing data, actuals, and revenue waterfalls.

That information is then available in Abacum for forecasting, reporting, analysis, and planning.

The result is a finance function operating from a shared source of truth rather than disconnected spreadsheets.

One of the biggest benefits has been improved forecasting confidence.

By combining billing forecasts, revenue data, and actuals across systems, Connor has significantly greater visibility into future performance.

"Having actuals alongside the forecast data has been really, really helpful."

Instead of relying on static spreadsheets and manual assumptions, the finance team can make decisions using connected, real-time information.

Supporting a Multimillion-Dollar Business with a Lean Finance Team

Perhaps the most significant outcome has been the efficiency Highway has gained.

Despite significant revenue growth, navigating a major finance transformation, and supporting increased investor reporting requirements, Connor remains the company's primary FP&A resource.

"We've scaled the organization through an investment period and a series transition, and it's still just me running the show."

The team has also dramatically accelerated reporting cycles.

What previously required significant manual effort can now be completed within days of month-end.

More importantly, finance can spend less time maintaining spreadsheets and more time supporting strategic decisions across the business.

The Difference Between Legacy Systems and Today’s Finance Technology

After implementing multiple generations of finance software throughout his career, Connor believes the biggest difference comes down to simplicity.

"It's just easier."

"You don't have to learn a whole new language."

"Everything works as intended."

"You click refresh, it flows through."

For lean finance teams operating in high-growth environments, that simplicity creates leverage.

Instead of fighting systems, teams can focus on understanding performance, improving forecasts, and helping the business make better decisions.

Results

Faster Reporting Cycles

Financial reporting that previously required significant manual effort is now completed within days of month-end.

Greater Forecasting Confidence

Actuals, billing forecasts, and revenue data are connected across systems, improving visibility into future performance.

Improved Operational Visibility

The team can analyze revenue and business performance with a level of detail that was previously difficult to access.

Lean Team Scalability

Highway has continued scaling while maintaining a highly efficient finance organization.

Foundation for Future Automation

With the core infrastructure in place, the team is now focused on dashboards, automated reporting, AI workflows, and deeper business insights.

Looking Ahead

With its new finance stack now in place, Highway is focused on unlocking the next phase of value.

That includes expanding reporting capabilities, automating workflows, and creating even greater visibility for leadership and investors.

For Connor, the benefits are already clear.

"You can already see the value add across the entire team. This is only going to help us going forward."

Highway's experience demonstrates that finance transformation isn't about replacing one tool with another.

It's about building a connected foundation that allows finance to operate strategically, scale efficiently, and keep pace with the growth of the business.