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), 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.
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 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)
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)
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, VP Finance & Controller, 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, VP Finance & Corporate Controller, Guideline
66% of executives now believe automation skills are essential for career advancement, according to this State of Accounting Automation report. That number is only rising.
AI isn’t the future – it’s already in your close
As our CTO Erik Yao 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
Ready for a personalized demo of Luca exploring your own data? Request one here
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.
