How Guideline Scales Revenue Accounting with AI-Powered Automation

The challenge: disconnected systems and slow revenue reconciliation

Guideline’s mission is to provide affordable, accessible retirement plans for small and midsize businesses (SMBs) – a market traditionally ignored by the major players in the retirement space. 

When Rebecca Wang joined Guideline in 2019, the fintech company was managing close to $1 billion in assets under management (AUM). Fast forward to today, and that number has skyrocketed to $17 billion. With this rapid growth, Guideline has faced a significant increase in revenue accounting complexity.

Despite the business’ expansion, Guideline’s accounting team remained lean. They processed massive transaction volumes each month, often exceeding millions of individual transactions. And with a homegrown billing system, Stripe payment data, and an ERP (NetSuite) that didn’t sync together, the Accounting team had no alternative but to spend countless hours on tedious, manual reconciliations.

“We were downloading revenue reports from Looker, pulling Stripe reports separately, and trying to reconcile everything in Excel,” Rebecca recalls. “Eventually, the Excel files just started crashing.”

The growing pains were real:

• Disconnected systems made revenue reconciliation slow, error-prone, and time-consuming
• High transaction volume + low AOV (average order value) created complex reconciliation challenges
• Manual processes stretched the close process from five days to nearly 10 days
• An impending audit created stress across the team

Rebecca knew that simply hiring more accountants to manage reconciliation manually wasn’t the answer.

The search for a scalable accounting automation solution

Guideline explored Zuora, Recurly, Chargebee, and other accounting automation tools. But every solution required them to migrate their billing system – which was a dealbreaker for Guideline.

They weren’t going to abandon their homegrown billing system, so they needed a tool that would integrate with what they already had.

That’s what made Leapfin stand out. Unlike other revenue reconciliation software providers, Leapfin didn’t require Guideline to change its billing system. Instead, Leapfin seamlessly integrated with Guideline’s internal systems, plus their critical revenue source systems including Stripe, QuickBooks, and NetSuite – finally bringing all their revenue data together into a single source of truth. 

The Leapfin impact: simplified reconciliation and automated accounting processes

Once Guideline implemented Leapfin, revenue reconciliation moved from a slow, manual process to an efficient, automated workflow.

1. Real-time reconciliation and error reduction

Leapfin automatically matches transactions across Stripe, bank statements, and Guideline’s homegrown billing system, eliminating painstaking and error-prone manual processes.

• Past-due invoices and aging receivables are flagged instantly
• Reconciliation errors are dramatically reduced
• Close time is back to 5 days or less each month

2. AI-powered revenue insights – without manual reporting

Before Leapfin, answering strategic revenue and business questions required hours of manually pulling reports . Now, with reporting through Leapfin, including AI-powered insights, Guideline’s finance team can:

• Track promotion and discount effectiveness over time
• Analyze refund trends and their impact on revenue
• Monitor sales tax exposure at a granular level
• Identify revenue fluctuations instantly and explain them to leadership

3. Lean team, enterprise-level impact

Despite the company’s rapid growth, Guideline’s core accounting team has stayed small – just six people. But with Leapfin handling finance automation, Rebecca’s team is able to punch far above their weight.

4. Audit-ready financials and smooth compliance

Guideline successfully passed its first audit with EY almost immediately after implementing Leapfin. With automated revenue reconciliation, data accuracy improved – making audits and financial reporting faster and easier.

What if Guideline lost its revenue reconciliation software?

Without Leapfin, Guideline would be forced to bring back the “human glue” – meaning more accountants, more manual work, and more risk.

“I’d have to hire a bunch of senior accountants just to handle reconciliations. And honestly, even if I wanted to do that, it’s getting harder to find the right talent. Automation isn’t just about efficiency – it’s about future-proofing the function. Younger professionals don’t want to spend their careers in spreadsheets. If you want to attract and retain great accounting talent, you have to give them the right tools.”

-Rebecca Wang, VP Finance Corporate Controller, Guideline

Advice for other accounting leaders

For finance and accounting teams looking to scale, Rebecca’s advice is simple:

• Don’t wait to automate. The earlier you implement revenue automation, the easier scaling becomes.
• Choose tools that work with your tech stack. Flexibility is key – switching billing systems, especially homegrown ones, isn’t an attractive option.
• AI is the future of accounting. Become fluent in automating the transactional work now so your team can focus on getting better at delivering strategic insights.