Why 2 in 3 software buys go sideways, and how to avoid it

Only 1 in 3 software buyers get through buying and implementation without unexpected disruption or regret, according to Capterra’s 2026 Software Buying Trends Report. The rest hit trouble along the way: integration problems, data migration issues, delays, or an app that turned out not to be the right fit.

When we asked finance leaders in our community how they choose apps, the answers sounded familiar. Most described their process as “vague”, “pretty loose” or “nothing formal”. That’s not a criticism. It’s what happens when something breaks and you need it fixed fast.

But a loose process tends to go sideways in one of three ways:

You get weeks into a trial before you find a deal-breaker.
You implement an app that solves the problem, but not the way your business needs it solved.
Comparing options gets so deep that you park it as “too hard”, and the broken process stays broken.

The good news: we have a a simple framework, built from what finance leaders in our community told us has worked (and what’s burnt them), so you can get to the right app faster.

1. Start with what’s broken, not with the demo

Demos are fun. But if you start there, you end up judging apps on their terms, not yours.

Write down what’s broken. Describe the process, where it falls over, and what it needs to do instead.
Map the data. Note what comes in, where it needs to go next, and who touches it along the way.
Turn that into your criteria. The list you end up with is your set of requirements. Every app gets measured against your process, not against its own feature list.

2. Make your criteria comparable

A list of criteria only helps if you can line apps up against it. Two things make that easier.

First, sort your criteria into two buckets:

Criteria that apply to every app you look at. These are things like depth of Xero integration, security, multi-entity support and pricing model.
Criteria specific to the category. For accounts payable, that might be the type of bill matching you need.

Second, decide how you’ll assess each one:

Yes/no for simple checks. “Does it support bill matching?” is quick to answer, but it won’t separate two apps that both say yes.
Specific answers where detail matters. “Does it do two-way, three-way or contract matching?” This is where your process mapping pays off.
A 1-5 score for the subjective stuff. Use it for things like how easy the app will be for your team to use.

3. Decide your make-or-breaks before you see anything

Not everything can be a 5 out of 5, so be honest about what you’ll compromise on.

The finance leaders we spoke to consistently hold the line on security, usability and depth of Xero integration. For some, it’s that black and white. As one put it: “If it’s not SOC 2, probably don’t even bother bringing the tool to the table.” They’re more willing to bend on feature fit.

Your list might look different, and that’s the point. What matters is writing it down before a demo, because once you’ve seen a tool you like, it’s easy to quietly rewrite your criteria to fit it.

One finance leader told us about an app they loved. They put real time into trialling it, then realised it didn’t handle multi-entity. If that had been written down as a make-or-break on day one, they could have ruled it out in five minutes.

4. Keep the comparison small and time-boxed

The goal is a confident decision, not an exhaustive one.

Use your make-or-breaks as a filter. Rule apps out on paper before you book a single demo, and aim for a shortlist of two or three.
Bring your process to the demo. Send the vendor your real scenario and ask them to walk through that instead of their standard script. Better still, trial it on a demo Xero file with test data.
Set a decision date upfront. A good-enough decision in four weeks beats a perfect one that never happens.

5. Get other people to pull your list apart

As one Stack Exchange member put it recently, you can’t write a requirement for something you’ve never been burnt by. Your list will have holes, and you won’t always be the one who spots them. The goal isn’t a perfect list. It’s a list good enough that others can tell you what’s missing.

Bring IT and security in early. They’ll have requirements whether you ask for them or not, and it’s far cheaper to hear them during planning than at sign-off. Certifications like ISO 27001, SOC 2 or CFO Techstack App Certification can help you shortlist, but they don’t replace the conversation.
Ask the people who’ll use it. The team doing the work day to day will spot gaps you won’t.
Ask other finance leaders. Someone has probably compared the same apps already, and that’s exactly what The Stack Exchange is for.

Get a head start. Launching: CFO Techstack's App Feature Comprison

Defining criteria from a blank page for every category is a lot of work, and plenty of finance leaders are doing that same work separately.

One told us “it would be helpful to have a comparison table across multiple apps”, so we’ve built one.

App Feature Comparison is now live on the CFO Techstack App Map, starting with 'Spend Management & Accounts Payable' (with more categories launching soon). It sets out the key criteria for that category and shows how each app measures up against them. Look for “Compare Apps” in that category. Read more about it here.

Treat it as a starting point, not the answer. Use it to kickstart your own list, then add the things only your business would know.

What’s one criterion you’d never skip now, because you learnt it the hard way?

Share it in The Stack Exchange, and tell us which category we should compare next.

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COMMUNITY INSIGHTS

🎤 How I stacked it

Perry Farrell, Financial Controller at AEI Music
Finalist: Stack Transformation of the Year for 2026 🏆

Perry Farrell is Financial Controller at AEI Music, which builds digital brands, labels and communities around electronic music, reaching 100 million engaged fans through its digital channels, festivals and spaces. Founded in 1996 with the launch of Drum&BassArena, its brands today include UKF and SubSoul.

When Perry joined, the finance function was recovering from a move from Aquila to Sage Intacct that had left the business without reliable financial data.

Over six months, the team migrated nine companies to Xero, rebuilt two years of accounting records and processed more than 60,000 transactions. Rather than replace the failed ERP with another all-in-one system, Perry convinced the directors to build an ecosystem of specialist tools around Xero, with the flexibility to keep improving it.

Here is their current tech stack:

Xero for Core Finance. Xero is the accounting platform across all nine companies, giving the team a reliable foundation to build on.
Mayday for Intercompany. Mayday manages intercompany transactions and reconciliations across the group, cutting the manual work of keeping balances aligned.
Apron for Spend Management. Apron brings payments, expenses and accounting together, and covers payroll, accounts payable and getting bill data into Xero.
Syft for Consolidated Reporting. Being implemented now for consolidated monthly reporting and recurring reports for different departments.
Claude for AI (on the radar). The team is looking at using Claude to automate parts of the finance function, such as handling the AP inbox.

See Perry's full stack.

If you want to showcase your stack contact jack.thiel@getmayday.com

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GIVE ME HOPE

A new face on Give Me Hope. We're excited to introduce Felix Matthews, an experienced CFO and now CFO in Residence at Mayday. He steps into Harriet's (big) shoes, to continue answering your important questions!

Reader's question:

"I've inherited a messy finance function and I don't trust the balance sheet. Where should I start?"

Felix's answer:

I've lived this, as I'm sure many readers have. It's a sinking feeling when you're looking through a sizeable balance sheet without supporting schedules.

Firstly, recognise that this isn't about going from bad to perfect in a caffeine-fuelled 80-hour week. It's a marathon, not a sprint, but by prioritising smartly and communicating clearly you can reach a set of numbers you can stand behind sooner than you might think.

Cash is king. A phrase I never tire of hearing, and thankfully a balance you can verify easily against the bank. Reconcile the aged receivables and payables and you're often close to confirming the working capital position, which gives you enough to start a simple cashflow forecast.

Next, reconcile by materiality so the largest balances are verified first. A £500k accrued revenue balance needs tackling before £5k of prepayments. But beware the small net balance hiding significant gross movements. I once innocently checked a suspense account before writing off the c.£1 balance, then banged my head on the desk when I realised it contained thousands of pounds of unrelated debits and credits.

If your detective work unearths issues everywhere you look, accept that some will have to wait until you have the basic picture. Keep a written log of everything you find, so deprioritising is deliberate, not forgetting, and you have a record of what you've inherited. With materiality in mind, some issues can often be deferred to year-end.

I've saved my most important tip for last: communicate. As soon as you realise the numbers need some TLC, share it with the stakeholders who matter, whether that's the CEO, the board or a founder. Bad news delivered early with a plan builds trust, and lets you own the solution and shape the timeline.

Every business (and balance sheet!) is different, but I've used this approach more than once to quickly understand working capital and the largest assets and liabilities, then chip away at the rest over time. You don't need every number to be right on day one. You just need to trust the ones that matter.

Have a question you’d like answered? Submit your questions here.

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EVENTS

Social: "Year End Close: Community Drinks" 🍻

Keen to catch up? Make sure you book your spot. Sydney has less than 5-seats remaining, the others aren't far behind!

Cape Town, Thursday 12 November: Book your spot
Adelaide, Thursday 3 December: Book your spot
London, Thursday 3 December: Book your spot [sponsored]
Melbourne, Wednesday 9 December: Book your spot [sponsored]
Sydney, Thursday 10 December: Book your spot [sponsored]
Perth, Thursday 10 December: Book your spot
Auckland [NEW], details TBC: Register your interest

Note, spots are limited so please only register if you intend to come along.

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Dinner: CFO Techstack x Ramp: Euro Launch

If you're in London, join us for dinner 🎟️

To mark Ramp’s UK and European launch, CFO Techstack and Ramp are hosting an exclusive dinner for finance leaders in London on 1 December. If you’d like to come along, register your interest here.

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Webinars: The Best in Finance x Tech

[UK] Why most budgets go off track by Q2, and how to stop yours: Mayday x ApprovalMax. Thursday 5 November, 2pm GMT.
With David Tuck (Mayday), Andrew Griffiths (HFL Education), Sam Newton (Gravitate Accounting) and Alex Keselman (ApprovalMax). Register

[APAC] Inside one finance leader’s AI playbook: CFO Techstack x ApprovalMax. Wednesday 18 November, 11am AEDT / 1pm NZDT.
With Inbal Rodnay (AI Expert) and Jesse Chapman (Harris Real Estate). Register

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THE STACK EXCHANGE

🧵 This week's top threads, from The Stack Exchange

The Stack Exchange is the place to connect with peers, stay on top of the latest apps and industry news, and work through the challenges that don't have an easy answer.

Want to join the conversation? Sign up free here.

NEW IN THE WORLD OF CFO SOFTWARE

🗞️ News from the stack-o-sphere

Pleo delivers a new accounting dashboard showing missing receipts, uncategorised expenses, pending approvals and more. Read more
Tipalti launches Treasury. Daily cash positions across banks, entities and currencies now sit alongside AP activity. Read more
Spotlight Reporting reworks its AI executive summaries to calculate the figures first and layers AI commentary on top. Read more

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WHAT THE DATA SAYS

📊 Stat of the week

Only 1 in 3 software buyers (34%) get through buying and implementation without unexpected disruption, regret or both.

Source: Capterra 2026 Software Buying Trends Report.

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MORE OF THE GOOD STUFF

And lastly, our top picks!

🎧 Podcast: EY Better Finance, "How CFOs can turn AI investment into enterprise impact". Listen here.

📝 Article: Why plugging governance gaps could be key to stopping Shadow AI in its tracks. Read here.

😆 Joke: I asked our CFO how she chooses software. She said it's like dating: decide your deal-breakers before you see the profile picture.

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