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Let's face it, payment management isn't exactly the sexiest part of running a startup.

As a CFO, you have to spend some of your days tracking cash burn rates, projecting cash flow, and trying to find the payment solution that will scale your business without breaking everything. After all, a staggering 82% of small businesses experience cash flow issues at some stage which can lead to their failure.

Any business looking to successfully ride out the storm should understand the importance of a modern payment management system to streamline financial operations, reduce costs, and be set up for scalability. Done right, it can be the foundation for fast, efficient growth. But with so many options out there, how do you choose the solution that’s right for your unique business needs? In this article, I’ll walk you through everything you need to know to find a payment management system tailored to your company’s priorities and growth plans.

Payment Management System Overview

A Payment Management System (PMS) is a platform that manages a company's monetary transactions, including expenditures, cash disbursements, and other cash management matters. Look at it as a central hub that doesn’t just cover paying bills but also helps to manage the entire payment lifecycle, from initiation to reconciliation, making it an indispensable tool for businesses of all sizes.

A PMS is usually cloud-based and allows you to optimize your payment processes – manage invoices, track requests and approvals, report insights, and automate payments. A good PMS will help you increase payment security and improve visibility and oversight for payments within your business.

Payment Management System Standard Features

When choosing a payment management system, it's essential to consider the features that best suit your business needs. Some critical features to look for include:

Invoice Management

A good PMS should handle invoice management, allowing you to easily create, edit, send, and track customer invoices. This will help keep track of all financial transactions related to sales, ensuring that there is a record of all payments due and received.

Payment Processing

Without efficient payment processing, businesses could experience delays in receiving payments or run into issues with declined transactions. The ideal payment management system should support multiple payment methods, such as credit cards, bank transfers, and digital wallets. A significant plus is being able to handle multiple currencies and integrate with popular payment gateways. 

Not all payment services provide seamless debit transactions. Find a system that not only handles debit efficiently but also offers insights into your liquidity position, ensuring you always maintain a healthy cash flow. ACH is also vital for direct debits and credits between banks. Ensure the system you're considering supports ACH transactions for both payable and receivable operations. Beyond simple transactions, an optimal system should also assist in the procurement process, offering tools that make purchasing and processing payments straightforward and efficient.

Invoice and Transaction Recording and Tracking

You'll want a system that records all your invoices, transactions, receipts, and payments in one place for easy tracking and reporting.  Look for a PMS that gives you a clear view of your financial health and offers real-time updates on payment statuses, automatic syncing with bank accounts, and categorization of expenses. It should also facilitate easy search and retrieval of past transactions, with filters for date, customer, amount, and more.

Receipt Generation

Receipts act as proof of transactions, serving as documentation for tax purposes for businesses and as proof of purchase for customers. Look for a platform that automatically generates and sends professional receipts for your customers upon payment. Options to customize receipt templates, add branding, and send via multiple channels (e.g., email, SMS) are advantageous. This particular feature will save you lots of time and effort while delivering an enhanced customer experience.

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Reporting and analytics tools are a must - you'll want insights into your cash flow, revenue, outstanding invoices, and transaction fees. The reporting feature should offer a range of pre-built reports like profit and loss statements, sales summaries, and expense breakdowns, with the additional ability to customize reports, set date ranges, and visualize data through charts or graphs.

Payment Management System Purchase Considerations

You shouldn’t solely rely on these standard features but also consider some important surrounding factors in evaluating systems, including:

Business Needs

You must first determine your must-haves because this ultimately determines the right software solution you end up with. For example, you should think about the types of payments you want to process, the volume of payments, and if it's likely to increase significantly over the next few years. Some systems are better equipped to handle high-volume processing, while others cater more to small businesses with lower volumes. Forecasting your payment volume growth allows you to choose a system that can scale with your needs.


The cost of these systems can vary quite a bit depending on the features and level of support offered. Some systems charge a monthly subscription fee based on the number of transactions you process. Others have tiered pricing plans based on features and functionality. A few providers offer completely free basic services to get you started. Think about your current and future needs to determine what level is right for you. If you're a small startup, a free or low-cost option may suffice in the short term. As you scale, you can always upgrade to a more robust plan.

Transaction fees are also common and are usually a percentage of the total payment amount plus a flat per-transaction charge. Compare the fees of different providers to make sure they seem reasonable and competitive. Some may waive or reduce fees for non-profits or for processing large volumes of payments.

Security and Compliance

Robust security is essential. Look for a system with strong encryption, multi-factor authentication, and role-based access controls. Encryption scrambles your data so only authorized parties can read it. Multi-factor authentication adds an extra layer of login security, often sending a code to your phone or email. Role-based controls restrict employee access to only the data and functions they need to do their jobs.

 For compliance, choose a system that meets standards like PCI DSS for handling credit card data and HIPAA if you deal with healthcare information. These certifications show the system meets strict security and privacy rules. 

Global Payment Coverage

For companies doing business internationally, a system that supports global payment methods and currencies is a must. Choose a vendor with experience handling cross-border payments that offers connectivity to payment networks around the world. They should support major payment types for each region, like SEPA for Europe, Faster Payments for the UK, and local card brands for the APAC region.

Integration and Compatibility

You also want to find a PMS that perfectly works with other business tools such as your accounting software, CRM, ERP, e-commerce platform, and anything else key to your operations. If not, you’ll end up with a disjointed mess of workflows and more headaches than any cost savings are worth. Look for options that easily sync data between systems to avoid manual data entry and ensure accurate record keeping. Some systems offer pre-built integrations with major platforms like QuickBooks, NetSuite, and Shopify. For other tools, API access may allow you to build a custom integration.

Customer Service

Don’t overlook the level of support offered by each vendor. Look for a provider with a proven track record of high-quality customer service to help you implement, manage, and optimize your payment management system. Options may include phone, email, and chat support as well as access to educational resources. Strong support will ensure you get the most out of your investment.

Redundancy and Uptime

For many tech companies, payments are mission-critical. Look for a system with built-in redundancy, load balancing, and failover to guarantee high availability. It should offer a minimum uptime of 99.9% to keep your payments running 24/7/365. Multiple data centers across geographies are ideal for redundancy.


Some vendors offer trials for a set number of days, while others provide access to a sandbox environment with dummy data so you can play around to your satisfaction. The idea is to test the tool out to anticipate how the system will handle your company’s unique workflows and use cases. Be wary – minor annoyances during a trial can turn into massive headaches after you’ve committed to a system. Be sure you’re making a worthy purchase and one that’s a right fit for your company.

Customer Reviews

When evaluating payment management systems, don’t just take the company’s word for it, check what others have to say. See what current customers really think about the system and service. Look for consistent praise or complaints across reviews. If a system gets overwhelmingly negative reviews mentioning poor customer service, clunky interfaces, or missing key features, that’s a big red flag. On the flip side, loads of four and five-star reviews mentioning a simple setup process, helpful support, and tools that make their jobs easier are good signs you’ve found a winner.

5 Best Payment Management Software for 2023

If you’re looking for a reliable option, here are 5 popular PMS that caught my eye:


Established in 2011, Stripe is like the cool kid on the block known for its premium payment processing features. They accept over 135 global currencies, integrate seamlessly with e-commerce platforms such as Drupal, WooCommerce, and Magento, have comprehensive reporting capabilities and subscription management tools, and are known for their transparent pricing. 

They offer no monthly fees as all charges are per transaction. For online sales, they charge 2.9% + 30 cents per transaction, and 2.7% + 5 cents per transaction for In-person card processing. An additional 1% charge applies for international and currency conversion.


Braintree, a subsidiary of PayPal, is a tech-savvy payment processing solution that has garnered a strong reputation in the industry. Here are some notable features:

  • Transaction costs stand at 2.59% + 49 cents per transaction
  • The software benefits from PayPal's expansive infrastructure
  • Supports payment in over 130 currencies
  • Integrates with PayPal and Venmo
  • Facilitates global transactions and fraud checks

Braintree is optimal for those who appreciate a straightforward payment processor and have a fondness for PayPal's resources.


FreshBooks is an accounting software primarily targeting freelancers, sole proprietors, and small businesses. Its purpose is to help with organization, managing payments, and sending invoices. You could term it a payment processing software designed for small-scale businesses with low-cost plans available. Pricing ranges from $8.50/month to $27.50/month with each plan offering a 30-day free trial.


Square is a renowned payment processing and point-of-sale (POS) solution catering to diverse businesses, from fresh startups to sprawling, multi-store enterprises. It's particularly appealing to smaller businesses and startups due to its budget-friendly fee system, which is adaptable to fluctuating incomes. Users only pay a small percentage and a fixed fee per transaction. 

For in-person card transactions, including prepaid gift cards, major credit cards, and mobile wallets like Apple Pay, Square imposes a fee of 2.6% + 10 cents. If a card is manually entered or used virtually, the fee is 3.5% + 15 cents per transaction. For online purchases and other digital transactions, the fee is set at 2.9% + 30 cents.


Tipalti is a cloud-based accounts payable solution that streamlines vendor billing processes. It's ideal for growing businesses with extensive bill processing needs, especially those that deal with international vendors. Some of the key features include:

  • The platform fee begins at $149 monthly
  • Supports payments in 196 countries with 120 currency options.
  • Suitable for businesses with numerous local and international vendors
  • Integrates with popular accounting software like QuickBooks, Sage, and Xero

Some Final Tips

The fear of choosing wrong and being stuck in a multi-year contract with a less-than-ideal partner is real. How do you cope?

Go With Your Gut

While the specs, security, and cost are important, don’t underestimate the value of a good partnership. If one vendor’s team gave you a good vibe and seemed genuinely interested in your success, that says a lot. People and culture fit matter.

Think Long-Term

A shiny new interface will wear off, but flexibility, scalability, and customer support are forever. Make sure any system you’re considering can grow with your business and provide the integrations you’ll need down the road. You don’t want to outgrow a solution in a year and have to go through this whole process again.

Don’t be Swayed by Price Alone

A lowball offer isn’t worth much if the solution can’t actually meet your needs. And a higher price doesn’t always mean better quality. Look at the total cost of ownership over the life of the contract, including additional fees for support, transactions, and add-ons. The cheapest upfront cost could end up costing you more in the long run.

Need expert help selecting the right Accounting Software?

We’ve joined up with to give all our readers (yes, you!) access to Crozdesk’s software advisors. Just use the form below to share your needs, and they will contact you at no cost or commitment. You will then be matched and connected to a shortlist of vendors that best fit your company, and you can access exclusive software discounts!

Read the Fine Print

I know, contracts are about as exciting as watching paint dry. But you need to understand all the terms, conditions, and commitments before you sign on the dotted line. Make sure there are no hidden fees or restrictive clauses that don’t align with your goals. If something seems off, ask about it. Your sales rep should be willing to clarify any confusing legal jargon.

Finally, when the sales reps start throwing around buzzwords like "frictionless," "supercharged," or "tech-driven"... tune them out for a second. Stay focused on what really matters for your business and your customers.

So there you have it. A quick primer on how to weed through the masses of payment management systems out there and find one tailored to your needs. Enjoyed reading this content? Subscribe to The CFO Club’s newsletter for more regular and interesting insights.

By Simon Litt

Simon Litt is the Editor of The CFO Club, where he shares his passion for all things money-related. Performing research, talking to experts, and calling on his own professional background, he'll be working hard to ensure that The CFO Club is an indispensable resource for anyone seeking to stay informed on the latest financial trends and topics in the world of tech.

Prior to editing this publication, Simon spent years working in, and running his own, investor relations agency, servicing public companies that wanted to reach and connect deeper with their shareholder base. Simon's experience includes constructing comprehensive budgets for IR activities, consulting CEOs & executive teams on best practices for the public markets, and facilitating compliant communications training.