Choosing the Right Financial Software: What Your CPA Wishes You Knew

Darla Redmond
Jun 20
3 min read

Let’s be honest—choosing financial software isn’t exactly exciting. It's somewhere between "doing taxes" and "cleaning gutters" on the fun scale. But if you’re running a business, the right financial software can save you more than just headaches—it can save you money, time, and even prevent IRS drama.

As CPAs, we live inside financial systems. We see what works, what fails spectacularly, and what creates unnecessary chaos during tax season. Here’s a behind-the-ledger look at what really matters when selecting your next accounting or financial software.

1. Clarity and Accuracy Trump Features

Every software boasts a buffet of features: dashboards, AI predictions, crypto integration—great, but irrelevant if the basics are a mess. We want:

Clean general ledger architecture
Consistent chart of accounts
Reliable bank reconciliation
Minimal “adjustments” come tax time

When we get handed a QuickBooks file with 400 unclassified transactions or a mystery “Ask My Accountant” bucket that’s overflowing, it adds hours (and billable hours, by the way).

2. Integration Over Isolation

You’d be surprised how many businesses use 4 different tools that don’t talk to each other:

One for invoicing
One for payroll
One for CRM
One Excel monster someone built in 2006 and guards like gold

Modern software should integrate seamlessly with:

Payroll providers (ADP, Gusto, etc.)
Banks and credit cards (with proper multi-factor authentication)
Tax prep software (for year-end magic)

If it can’t integrate, you’re basically hiring someone to copy-paste numbers—and trust me, human error loves copy-paste.

3. Scalability: Your Business Will (Hopefully) Grow

We always ask clients: Do you want to outgrow your system in 2 years? If you have plans to scale, look for:

Multi-user support with role-based permissions
Multi-entity or location capability
Audit trails and approval workflows

A cheap solution today might mean a painful data migration tomorrow—and we’ve seen more than one client pay double just to “upgrade” out of their own mess.

4. Security: Because Fraud Isn’t Just a Netflix Show

In the age of phishing, ransomware, and bored teenagers with hacking tools, we care deeply about:

Two-factor authentication
Role-based access
Automatic backups and encryption

Some clients still use desktop software with one login for “everyone.” That’s like giving your house keys to everyone who ever rang the doorbell.

5. User Experience—Because Your Bookkeeper Isn’t a Robot

You don’t need to be a CFO to navigate your books. The best tools empower non-financial staff to:

Enter data correctly
Run basic reports
Flag errors before they turn into disasters

We love when clients understand their P&L without needing a translator. The clearer the interface, the fewer the mistakes—and fewer panicked emails to your CPA on April 14th.

6. Support and Ecosystem: You’re Not Alone (Unless You Choose to Be)

We prefer systems with:

Strong community forums
Active accountant portals
Real human customer support that isn’t a bot pretending to care

If we, as your CPA, can’t access or work inside your software efficiently, that’s a red flag. You’re paying us to help—don’t lock us out.

Final Word: Ask Your CPA Before You Buy

Don’t just choose what’s trending or cheapest. Financial software is a tool, not a trophy. Before buying, ask your CPA (yes, that includes us at Redmond CPA) to: