---
title: What's Holding Back Your Automation Strategy? Real Talk From Controllers in the Trenches
description: Tips from Controllers on how to launch your accounting automation strategy | where to start, how to resource it, and what success can look like | Leapfin
image: https://www.leapfin.com/hubfs/blog.png
---

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# What's Holding Back Your Automation Strategy? Real Talk From Controllers in the Trenches

[ Dave Bor, Director of Content at Leapfin ](https://www.leapfin.com/blog/author/dave-bor)

 Updated on  October 28, 2025

![What's Holding Back Your Automation Strategy? Real Talk From Controllers in the Trenches](https://www.leapfin.com/hubfs/blog.png)

Automation isn’t just a buzzword – it’s the difference between spending close week buried in spreadsheets or stepping into a strategic finance leadership role. But even the most forward-thinking teams admit: it’s hard to know where to start, how to resource it, and what success even looks like.

At our 2025 virtual conference, Transform ([all sessions on-demand here](https://transform.leapfin.com/2025)), accounting and finance leaders got real about the friction. Whether it’s fear of failure, over-reliance on Excel, or just not knowing what’s out there, the blockers are real – but solvable.

[Learn about overcoming roadblocks to YOUR automation success.](https://www.leapfin.com/webinars/building-a-business-case)

## Why automation stalls – and what actually moves it forward

In our excellent Rise of the Super-Controller panel, VP Controllers from Eight Sleep, Help Scout, and [Guideline](https://www.leapfin.com/story/guideline) didn’t sugarcoat it. They’ve lived through broken processes, data gaps, and tools that didn’t deliver. But they also shared what helped them make progress:

### Start with the low-hanging fruit

When automation gets framed as a huge ERP migration or all-at-once accounting process transformation, it feels unreachable. But the best teams started small – targeting tasks that may only save 30 minutes individually, but compound across workflows.

> “We’re at the stage of tackling ‘low-hanging fruit’ – those smaller tasks that individually take 30 minutes, but collectively steal days.” -Alicia Arntson, CPA, VP Controller, Eight Sleep

### Expect automation to expose your weaknesses

Tech won’t cover up messy data – it’ll amplify it. And that’s a good thing. Teams that lean in and fix foundational issues get stronger with every automation cycle.

> “The tools are great – but they expose where you have data gaps or data issues that need to be addressed. The tools are only as good as the data that goes into them.” -Alicia Arntson ([more context in Alicia's video clip on LinkedIn](https://www.linkedin.com/posts/leapfin_finance-tools-are-only-as-good-as-the-data-activity-7322615494233018370-iswl?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAC4xY4B5Ndc4Mu0EhwZpgj-AD4Eq_-nWqc))

### Don’t wait for a clean slate

The path to automation rarely starts with a perfect process. It starts with accounting teams being willing to evolve – and experiment. Sometimes that means prototyping tools on top of messy systems to learn what should change.

> “We submit a lot of tickets to engineering. We see everything – because we’re the ones scrubbing the data. So we’re driving the system changes too.” -Alicia Arntson ([see related video clip here](https://www.linkedin.com/posts/leapfin_transform-rewind-how-controllers-are-driving-activity-7321199287466430464-eCPe?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAC4xY4B5Ndc4Mu0EhwZpgj-AD4Eq_-nWqc))

### The skills behind the systems

When automation becomes part of your culture – not just a project – your hiring mindset has to evolve too. Everyone on your team doesn’t need to be a Python wizard, but curiosity about systems is no longer optional.

> “Everyone on my team needs to be part-accountant, part-systems thinker, and a little bit coder.” -[Jenny Rush](https://www.linkedin.com/in/jenny-rush-8950836/), VP Finance & Controller, [Help Scout](https://www.linkedin.com/company/help-scout/)

> “You do need to have a technology mindset. I have people on my team now learning to code – not because they have to, but because it helps us pull better reports and analyze faster.” -Jenny Rush

> “In budgeting, I now think in three categories: people, systems, and external fees. Systems are growing fast.” -[Rebecca Wang, CPA](https://www.linkedin.com/in/rebecca-wang-cpa-82735816/), VP Finance & Corporate Controller, [Guideline](https://www.linkedin.com/company/guideline/)

66% of executives now believe automation skills are essential for career advancement, according to this [State of Accounting Automation report](https://www.leapfin.com/state-of-automation-for-revenue-accounting). That number is only rising.

### AI isn’t the future – it’s already in your close

As our CTO [Erik Yao](https://www.linkedin.com/in/erikyao/) reminds us, AI doesn’t just live in some hypothetical forecasting future – it’s already powering today’s reconciliations, audit prep, and exception spotting.

> “This isn’t just about replacing menial tasks – AI is helping with reconciliation logic, critical thinking, and finding errors that used to take hours.” -Erik Yao, CTO, Leapfin

One finance leader used Luca, our AI revenue data reporting and exploration agent, to find and validate 100+ revenue recognition events tied to a single prepayment in seconds. Another used it to pull audit test transactions without a single spreadsheet.

Want a helpful intro to AI – plus a short demo of Luca? [Watch this extended video clip on LinkedIn](https://www.linkedin.com/posts/leapfin_leapfin-cto-provides-intro-to-ai-for-finance-activity-7324112094423883776-QMsK?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAC4xY4B5Ndc4Mu0EhwZpgj-AD4Eq_-nWqc)

Ready for a personalized demo of Luca exploring your own data? [Request one here](https://www.leapfin.com/lp/newsletter/offer/product/meet-luca-ai-make-reconciliation-easy-and-fast) 

### Real talk: fear slows us down

Controllers also acknowledged something most automation blogs skip: fear. Fear of replacing jobs. Fear of building the wrong thing. Fear of change. But that’s exactly why now is the time to lean in.

> “AI isn’t going to replace you. People who know how to use AI are going to replace you.” -Rodrigo Brumana, CFO, Poshmark

And as Rodrigo also pointed out, smart system investments don’t just increase speed – they reduce stress:

> “Over the past 18 months, we implemented four systems here, including Leapfin. Today, the organization has amazing working conditions. We are faster, more accurate, and – this is important – drama free.” -Rodrigo Brumana

### So where do you start?

Try these first:

- Automate one recurring month-end task (e.g. transaction data consolidation, credit matching, etc.)
- Ask your team: what’s one workflow we dread but do monthly?
- Choose one small process to prototype in your existing tools or with a free AI prompt
- Don’t chase ROI – chase relief. It will scale.

 

The modern Controller isn’t just reconciling the books. They’re building better systems, faster closes, and higher-value teams.

And it starts with the next 30 minutes you never want to spend again.

### See how Leapfin works

Get a feel for the ease and power of Leapfin with our interactive demo.

Start interactive demo

Leapfin is the trusted AI infrastructure that powers your entire record-to-report process at scale. Leapfin helps companies accurately account for and report on revenue by standardizing large volumes of siloed, inconsistent operational data into usable, GAAP-ready financials and automating manual accounting tasks. 

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