Your weekly go-to guide to transform your finance function into a strategic powerhouse.
Welcome CFO Techstack Community 👋,
In last week’s newsletter, we explored one of the toughest hurdles for finance teams—month-end. Tyler Caskey shared his expert strategies to help your team streamline the process and tackle it with confidence.
This week, Tyler takes it a step further by diving into your top resolutions for transforming month-end in 2025. He highlights the key triggers that signal it’s time to automate your processes—whether it’s speeding up month-end or boosting team engagement. Let’s explore how smart automation can redefine the way your finance team works.
FEATURED ARTICLE
When to automate: Key triggers for transforming your finance team
We asked the CFO Techstack community: What’s your top resolution for improving month end in 2025?
43% said reducing manual work. It’s a top priority – but achieving it can be challenging. That’s where automation comes in.
Automation is transforming finance teams, making them faster, more efficient, and focused on what really matters. But how do you know when it’s time to start automating? Tyler Caskey from TheBeanCounters shared his thoughts on the key moments that signal it’s time to embrace automation tools like Mayday, Syft Analytics, dataSights and more.
1. Your month-end process is too slow
If your month-end process is dragging on, it’s a clear sign that it’s time to consider automation. With only 22 working days in a month, spending five of them looking backwards on month-end tasks leaves you with just 17 days to focus on moving forward. Aim to close the books in one day or as quickly as possible. I'm sure there's an entity out there with like 100 Xero files that can cut a week off their month end with ease. Get the team to absolutely nail that backward-looking work, then use the rest of the month to add value—whether it’s creating budgets, automating processes, or driving business improvements.
2. You’re a CFO doing accountant-level work
The second trigger for me is if you’re a CFO, but you’re stuck doing accountant-level work instead of focusing on CFO responsibilities. I’ve been guilty of this myself. Whenever I step into a new entity, I’ll dive into the cash, dig through payroll, and comb through the balance sheet to find errors. It’s how I get a clean starting point and learn the business. But if I’m still doing that weeks or months later, that’s a problem. Continuing to handle tasks like basic balance sheet reconciliations, intercompany recs, or fixing recurring errors is often a sign that automation is overdue. That’s when I step back and ask myself, ‘Am I spending my time on work that could be automated? What’s the opportunity cost here?’
3. Your team is stuck in manual, unengaging work
The last big trigger for me is engagement—keeping your finance team motivated and happy. I’m a big believer that every month, you should make a small improvement. That could mean improving something detailed like the tax rec one month, fixing intercompany issues the next, or streamlining credit card recharges after that. Manual, repetitive tasks are a key sign it’s time to automate. If I’ve got someone on my team doing something manually that isn’t engaging and could be automated for a small cost, it’s a no-brainer. Those are the tasks you should tackle first. The more you can eliminate tedious, unfulfilling work, the more engaged and productive your team will be.
By identifying the right moments to automate, you can reclaim valuable time, focus on high-value tasks, and create a more engaged, motivated team. Don’t wait for inefficiencies to pile up—start small, automate smart, and set your team up for long-term success.
COMMUNITY INSIGHTS
🎤 How I stacked it
Josh Hawkey, Financial Controller at Tracksuit, shares their tech stack
Tracksuit is a New Zealand-based SaaS platform that provides beautiful, affordable, and always-on brand tracking. Tracksuit provides a simple way for marketers to track brand health, demonstrate return on marketing spend and answer the question, “Is what we’re doing working?”
Josh told us, "As the Financial Controller at Tracksuit, I am involved in every aspect of the finance function. Over the past six months, I’ve been focused on upgrading the function by implementing best-in-class software. My day-to-day includes reporting, forecasting, invoicing, and basically anything involving a dollar sign."
Here's what Josh and their team are using:
Xero for Accounting:Xero is the glue that holds everything together at the general ledger level with all of the other tools we plug into it.
Subskribe for Invoicing and Rev Rec:Subskribe integrates with HubSpot to streamline invoicing and revenue recognition allowing our sales, finance, and customer success teams to operate on one source of truth.
CreditorWatch Collect for AR Management:CreditorWatch Collect is Xero reminders on steroids allowing us to have custom reminders and automatically escalate.
Airwallex for Cards, Expense Claims and International Payments:Airwallex is becoming our one stop shop for all things cards, reimbursements and payments (Read more about how we use Airwallex here).
HiBob for HRIS:HiBob does everything you expect of an HRIS and also allows us to consolidate our global payroll changes and leave requests.
G-Accon for Reporting: Sometimes, nothing matches the flexibility and power of spreadsheets. We use G-Accon to deliver daily cash balances, track upcoming bills and unreconciled transactions at a group level.
VendorSage for Saas Spend Management:VendorSage assists in negotiating contracts and tracking SaaS spend across the business.
Mayday for Intercompany: Finally, thanks to Mayday, we’re reconciling our intercompany accounts with ease.
🧵 This week's top threads, from The Stack Exchange
The Stack Exchange is a Slack forum for connecting with peers, sharing insights, and staying updated on apps and industry events—helping you transform your finance function into a strategic powerhouse.
Here are this week's top 3 discussions from The Stack Exchange:
Brex secures $235 million credit facility. Learn more
Spendesk introduces Apple Pay in the UK. Learn more
ChurnZero launches new superpower for customer teams with Engagement AI. Learn more
WHAT THE DATA SAYS
📊 Stat of the week
While 85% of CFOs recognise the importance of spend culture, only 31% have one in place. For those businesses that do prioritise defined spend cultures, 49% reported stronger controls, while 41% say they've achieved higher profitability.
Managing finances across multiple entities can be complex—but it doesn’t have to be. If fragmented data, manual processes, and limited visibility are holding you back, this 45-minute webinar will equip you with the strategies to take control.
Join the New Year revolution. Kickstart 2025 with fresh insights and proven workflows for month-end success. Throughout January, we surveyed the CFO Techstack community to uncover the biggest month-end challenges finance leaders face—and their resolutions for the New Year.
This session will cover how the latest financial management tools allow finance leaders to save time, streamline operations and boost efficiency, effectively enabling them to work smarter, achieve more and live better.
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