0425 From Manual To Magic Blog B

In conversations with finance teams navigating automation, a familiar pattern often emerges. Leaders know their accounting operations need to evolve, but the path forward isn’t always clear. The sheer scope of a transformation can be paralyzing.

You can get out of this state of shock and start making strides when you realize you don’t need to overhaul your entire accounting function overnight.

I recommend a more pragmatic approach: Begin with a narrow focus, apply agile methods and build momentum through small, structured wins. Agile, originally a software development methodology, works exceptionally well in finance when adapted thoughtfully. Applied to accounting, it can give you a structured way to modernize processes without sacrificing efficient daily operations.

When you get it right, the transformation can feel like magic — not because it’s effortless but because of how dramatically it simplifies the work.

Step 1: Define your project and assemble your team

Agile begins with a clear purpose. What part of your accounting cycle is ripe for change? It might be:

  • Reducing manual effort in preparing recurring journal entries
  • Standardizing reconciliations for high-risk balance sheet accounts
  • Improving visibility and control over intercompany eliminations

Once you’ve selected your initial focus, identify a small, cross-functional team. That might include one or two accountants who manage the process today, a member of your IT or automation team and a team lead or controller to serve as the product owner.

Your goal is to scope out a project small enough to deliver real progress in a few weeks, rather than trying to automate everything.

Step 2: Choose your sprint cadence

Agile teams work in time-boxed cycles called sprints. In software, sprints typically last two weeks. This same rough sprint cadence also works well for finance. In my experience, two staggered sprints per month allow you to maintain momentum without interfering with the month-end or quarterly close cycle.

The key is to make the sprint regular and predictable. Every two weeks, your team should:

  • Review what was completed
  • Set clear, achievable goals for the next sprint
  • Prioritize the next set of tasks
  • Assign ownership based on capacity

This rhythm helps you maintain forward progress even amid daily demands and the ebbs and flows of a typical fiscal year.

Step 3: Start with process selection and discovery

Your first sprint should focus on understanding the process you want to improve. Let’s say you choose to automate a journal entry for prepaid expenses. This first step isn’t writing scripts. You need to understand how the process works today (pain points included), what systems and data are involved, what artifacts exist and what volume and complexity you’re dealing with. 

Say you’re working on a recurring entry to allocate depreciation. You need to uncover: how the entry is generated today, what triggers it and when in the accounting period, which accounts it impacts, what documentation and validations exist and who reviews or adjusts it before it’s posted to the general ledger. You might also need to gather artifacts like Excel templates, email approval flows or ERP screenshots. These are your starting points for making sure your automation reflects a real workflow rather than an ideal one.

Don’t underestimate the importance of the discovery phase in making sure your automation efforts are grounded in reality.

Step 4: Break down tasks and build your backlog

Once you’ve scoped your process and gathered what you need, it’s time to translate your findings into tasks. Some examples:

  • Map the current workflow in a flowchart and make sure you cover any places where the process could fail or have to start over
  • Identify fields and logic needed for journal entry automation, so you know the required data and calculations
  • Review automation platform capabilities (e.g., templates or connectors)
  • Write acceptance criteria for a successful automation — this is how you’ll prove your new automation is working
  • Prepare test data or validate entry logic, and be sure to include several examples of the different kinds of data you might see to cover the most probable cases 

Tasks that can’t be finished in this sprint go into your backlog. You can reprioritize that backlog after each sprint based on what you’ve learned or what’s most urgent.

Some tasks may expose gaps in how the process works today, and that’s a good thing. Agile sprints are built for learning, not perfection.

Step 5: Communicate, adjust and demo progress

A key agile principle is transparency. Short, regular check-ins — say, 15 minutes twice a week — keep everyone aligned and aware of blockers. No need for slides or long updates. A quick “What’s done, what’s next and what’s in the way?” is usually enough. 

At the end of the sprint, reconvene for a demo. Even if you didn’t automate the entire process, showing a prototype or workflow map can energize your team and stakeholders. Use what you learn to shape the next sprint.

Where to start? Go for high pain, low complexity

If you’re not sure where to begin, I often recommend focusing on account reconciliations. They’re a consistent source of friction and effort, especially for temporary account balances or frequently adjusted liabilities. But many can be standardized or automated with relatively little effort.

For example, bank reconciliations follow a predictable pattern. Accrual accounts only need simple threshold logic. And intercompany receivables/payables might just require timing alignment.

Journal entries are another good candidate, particularly if they’re recurring and related to depreciation, allocations or amortizations. Their fixed logic and regular intervals make them perfect for early wins.

The record-to-report (R2R) cycle contains many interconnected subprocesses that are ideal for incremental automation. Applying agile to this domain brings visibility and momentum to your transformation efforts while minimizing risk and burnout.

Agile is how finance gets things done

Finance doesn’t often borrow from the world of software development, but it should. The pressure is real today to modernize, optimize and transform while still closing the books on time — no small feat.  Agile gives your accounting team a way to improve processes iteratively, without waiting for perfect conditions or massive budgets. They get a repeatable structure and still have space for experimentation. Once they see how agile can turn a painful process into a streamlined one, you’ll have the buy-in you need to scale your automation strategy across your finance organization.

You won’t need a wand, just the right structure, people and mindset. Those create the real magic.

About The Author

Caitlin Steel's Avatar

Caitlin Steel

Caitlin Steel is a passionate product leader with a mission to revolutionize the accounting profession. As VP of Product Management for Finance Automation at Redwood Software, she leverages her deep understanding of both the challenges and potential of finance to develop innovative automation solutions.

Caitlin's accounting journey began in the ‘80s, grappling with the first version of Excel. This experience ignited a lifelong quest to make accounting not just functional but inspiring. She brings a unique perspective, informed by her prior roles as a CFO and senior leader in product management at BlackLine, XaCTLY, OpenGov and other successful software companies. This experience has instilled in her a commitment to delivering high-impact products that empower teams.

When Caitlin steps away from the world of finance, she chases adventures. She's a champion for rescue dogs and enjoys lending a hand on her sister's ranch. This zest for new experiences fuels her creativity and brings fresh perspectives to her work.

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