Choosing the Right Accounting Software

Lee McClellan, CPA - Owner & Operator of Filan

Authored by Lee McClellan, CPA

Founder & Operator of Filan Advisory

Choosing the right accounting software for your organization can feel a lot like choosing a partner – it’s a big decision with plenty of options to weigh and a long-term commitment to consider. Pick the right one, and it’s a match made in heaven. Pick the wrong one, and you might find yourself in long, frustrating conversations with the “in-laws” (i.e. customer support, the implementation team, etc.).

In the following article, we’ll discuss some of the basic differences between small- and medium-sized business accounting software, the absolute essentials you should look for in the right match, and some of the additional features you might consider given your firm’s specific circumstances.

Small Business & Accounting Software

Small business owners are often looking for a combination of simplicity, affordability, and basic functionality when selecting accounting software. But beyond these key factors, the decision often involves balancing a variety of other priorities such as control, ease of use, and scalability.

What Small Businesses Typically Look For in Accounting Software

1. Affordability

Small businesses operate on tighter budgets, so finding accounting software that fits within financial constraints is critical. Subscription-based models, or Software-as-a-Service (SaaS), are popular because they offer lower upfront costs and predictable monthly fees. The focus is on getting the best value without sacrificing essential features.

2. Control & Ease of Use

Many business owners and their teams are not accounting experts, so the software needs to be intuitive. Clear navigation, easy-to-follow training, and responsive customer support are highly valued. Transparency in pricing and features is also a priority, so businesses know exactly what they’re paying for.

3. Features & Functionality

For many small businesses, industry-specific features are important. For example, construction companies might need project-based accounting, while retail businesses require inventory management. Standard features like financial reporting, payroll management, and tax management should also be easy to access and tailored to the specific needs of the business.

4. Scalability & Integration

As businesses grow, their accounting needs often evolve. Choosing a scalable solution that can grow alongside the business is crucial. This includes the ability to integrate the accounting software into existing technology stacks, ensuring it can connect seamlessly with other tools like customer relationship management (CRM) systems, e-commerce platforms, or payroll services. Cloud-based accessibility is also a big draw, allowing business owners and their accountants to manage financials from anywhere with secure access.

The Core Features of Small Business Accounting Software

When small businesses evaluate accounting software, they typically focus on a few core features that help them manage day-to-day financial tasks and make informed decisions.

Transaction Entries

Recording daily transactions, whether it’s sales, purchases, or expenses, is a fundamental function. The software needs to make this process simple, with automation capabilities like importing bank transactions to reduce manual entry.

Payroll Management

Payroll can be complex, especially as a business grows. The right software will make it easier to handle employee payments, calculate taxes, and generate payroll reports – ensuring compliance with tax regulations. Typically, the software will also come with integration features with third-party payroll processors.

Financial Reporting

Regular financial reports, like balance sheets and income statements, are essential for understanding the business’s financial health. With built-in reporting features, business owners can easily monitor cash flow, profits, and expenses, allowing for more strategic decision-making.

Tax Management

Staying on top of tax obligations is often a pain point for small business owners. Accounting software should simplify this by calculating taxes, tracking deadlines, and ensuring compliance with both local and federal regulations.

Information Strategic Decision-Making

Beyond the basics, businesses need accounting tools that support strategic planning. Features like budgeting, forecasting, and cash flow management help businesses anticipate future financial needs and make data-driven decisions to support growth.

Invoicing & Billing (Accounts Receivable)

Timely and accurate billing is key to maintaining cash flow. Good accounting software will allow businesses to create and send invoices, track payments, and manage customer accounts.

Expense Tracking & Accounts Payable

Managing expenses and paying vendors on time are critical to smooth operations. Automated expense tracking features make it easier to record and categorize expenses, while accounts payable functions ensure that bills are paid on schedule.

Inventory Management

For product-based businesses, inventory management can be a challenge. Software that integrates inventory tracking with financial records helps businesses maintain optimal stock levels and understand the impact of inventory on their bottom line.

Balancing Simplicity & Functionality

While small businesses often prioritize simplicity, they also need software that offers enough functionality to handle their growing needs. The key here is to find a balance between a user-friendly interface, a robust set of features to enable strategic insights, and a platform that can growth with your firm – all at an affordable price point. There can be a temptation to outfit your organization with the biggest and baddest software. Just remember – you wouldn’t put off-roading tires on a Mercedes, right? Likewise, pick an accounting software that fits your current situation well.

Medium-Sized Business & Accounting Software

As medium-sized businesses grow, so do their financial complexities. Finding the right accounting software becomes less about just handling the basics and more about strategically managing finances across departments, locations, and even countries. Operational efficiency, scalability, and advanced insights are key priorities for businesses at this stage. It’s no longer just about keeping the books in order – it’s about using financial data to drive informed decision-making and optimize performance across the board.

While many of the core features small businesses need remain essential, medium-sized businesses require more robust tools that go beyond day-to-day bookkeeping. Let’s break down some of the key factors that medium-sized businesses look for when selecting accounting software.

The Focus Shifts: Strategic Financial Management

1. Operational Efficiency at Scale

As businesses grow, the need for automation and streamlined processes becomes critical. Medium-sized companies need accounting software that can handle higher transaction volumes and support the standardization of processes. Automation tools—like those that reduce manual data entry or automatically categorize expenses—allow finance teams to focus on more strategic tasks rather than getting bogged down in routine work.

2. Advanced Insights

Medium-sized businesses require deeper, more detailed financial insights to inform their decision-making. This means software must provide advanced reporting and analytics capabilities, helping businesses identify trends, forecast cash flow, and make strategic adjustments based on real-time data.

3. Scalability

A growing business can’t afford to outgrow its software. Scalability is crucial, and accounting systems need to easily adapt to increasing transaction volumes, more users, and new locations – whether that means a larger workforce or global expansion.

4. Compliance & Risk Management

With growth comes increased regulatory responsibility. Compliance with tax laws, industry regulations, and internal controls becomes more complex. Accounting software for medium-sized businesses should include features like audit trails, customizable reporting to meet compliance standards, and robust security measures to protect sensitive financial data.

5. Interdepartmental Collaboration & Integration

The need for accounting software to integrate seamlessly with other systems is more pronounced for medium-sized businesses. Whether it’s an Enterprise Resource Planning (ERP) system or a Customer Relationship Management (CRM) tool, accounting software must work well within the larger tech stack to ensure smooth interdepartmental collaboration. Financial data doesn’t exist in a vacuum – it needs to inform and be informed by the sales, HR, and operations teams, creating a cohesive ecosystem of business insights.

Key Features for Medium-Sized Business Accounting Software

While medium-sized businesses still need the core accounting features – like transaction tracking, invoicing, and financial reporting – additional considerations arise as they scale.

Advance & Diverse Accounting Capabilities

As companies expand, managing multiple subsidiaries or business units becomes more common. Accounting software should support these needs through consolidation features, allowing for easy aggregation of financial data across different entities. Additionally, advanced financial reporting and project-based accounting become important for businesses managing multiple revenue streams or cost centers.

Custom Reporting & Analytics

Pre-built reports are great for general purposes, but medium-sized businesses often require custom reporting to answer specific questions about financial performance. Software that offers customizable reporting and advanced analytics tools enables businesses to track KPIs, perform variance analysis, and create bespoke financial dashboards.

Flexible Integrations with Existing Systems

Integration flexibility is key for medium-sized businesses. They need their accounting software to integrate smoothly with other critical business systems like ERP platforms, CRM software, and HR systems. This ensures that data flows seamlessly between departments, minimizing the need for manual data entry and reducing the risk of errors.

Multi-Currency & Global Accounting

As businesses expand internationally, handling multiple currencies and adhering to various accounting standards becomes a priority. Software with multi-currency capabilities simplifies international transactions and financial consolidation. Additionally, global businesses need to manage taxes, financial reporting, and compliance across different jurisdictions—features that standard small business solutions typically don’t offer.

Enhanced Data Security

With more financial data at stake, data security becomes a bigger concern for medium-sized businesses. Accounting software needs to provide robust security features, including data encryption, secure access controls, and regular security audits, to protect sensitive financial information from breaches.

Additional User Access & Role-Based Permissions

As businesses grow, so do the number of people who need access to financial data. Role-based permissions allow businesses to control who can view, edit, or approve certain financial information, ensuring that only authorized personnel can access sensitive data.

Data Migration & Implementation Support

Transitioning to new accounting software can be daunting, especially for businesses with years of financial data to migrate. Medium-sized companies look for software providers that offer extensive implementation support, from data migration services to in-depth training for their finance teams.

Audit Tracking Features

Keeping track of who made changes to financial records and when is essential for compliance and internal controls. Audit tracking features ensure businesses can maintain an accurate history of all financial transactions and edits, simplifying both internal audits and external regulatory compliance.

Multi-Department / Multi-Location Coordination

Managing finances across different departments or locations is a challenge for growing businesses. The right accounting software should support multi-department coordination, allowing businesses to track financial performance by location, department, or project. This is particularly important for companies with complex organizational structures or businesses operating in multiple locations.

Looking Forward

Choosing accounting software for a business goes beyond managing day-to-day finances. It’s about finding a system that not only meets today’s needs but also supports the company’s long-term growth and strategic goals. By prioritizing the key functionalities & capabilities right for their organization’s growth phase, businesses can choose software that helps them make informed decisions and maintain financial health as they expand. With the right infrastructure in place, leaders can focus on what matters most – growing the business.

Let’s Chat

If you’re looking to explore how the right accounting system can elevate your operations, we’re here to help. Let’s dive deeper into your specific needs and uncover the best solutions tailored to your business. Contact us today to schedule a consultation and start the journey toward smarter, more strategic financial management.

Explore

Related Articles

Who We Are

At Filan, we drive ambitious growth by blending deep expertise, entrepreneurial insight, and cutting-edge technology. We thrive at the intersection of financial leadership and technology, delivering tailored solutions that empower businesses to scale confidently.

Built on trust, agility, and innovation, we adapt to every client’s needs, providing clarity, confidence, and measurable results.