Tax season can be a daunting time for small businesses, but fintech innovations are transforming how owners approach preparation and compliance. To explore this shift, we’ve gathered insights from industry leaders, including CEOs and Chief Growth Strategists, who share actionable strategies for efficiency. From leveraging tools like FreshBooks for simplified tax prep to integrating bookkeeping and payments for real-time tracking, these nine expert-backed tips provide a roadmap to streamline processes and maintain compliance.
- Adopt FreshBooks for Easy Tax Preparation
- Use Stripe’s Tax API for Accuracy
- Utilize Xero’s Reconciliation Feature
- Connect Avalara for Multi-State Compliance
- Automate Taxes with QuickBooks
- Link Fintech Tools to Bank Accounts
- Connect Payment Processor to Accounting Software
- Leverage Fintech for Automated Tax Tasks
- Integrate Bookkeeping and Payments for Real-Time Tax Position
Adopt FreshBooks for Easy Tax Preparation
Adopting fintech has revolutionized how we handle taxes. We use FreshBooks, which helps us manage our finances and stay compliant. One standout feature is the invoicing system. FreshBooks automatically tracks our income and categorizes expenses, making tax preparation straightforward. For example, during a recent project, we used FreshBooks to invoice clients and keep track of our expenses. When tax season came, generating the necessary reports was a breeze, and we filed without a hitch.
Spencer Romenco
Chief Growth Strategist, Growth Spurt
Use Stripe’s Tax API for Accuracy
I discovered that using Stripe’s tax API integrated with our payment system automatically handles sales tax calculations across different states, saving us countless hours of manual work. When we implemented this, our tax preparation time dropped from weeks to just a few days, and our accuracy improved significantly. For small businesses just starting out, I’d recommend looking into TaxJar—it’s more affordable than enterprise solutions and integrates well with most e-commerce platforms.
John Cheng
CEO, PlayAbly.AI
Utilize Xero’s Reconciliation Feature
Fintech solutions have made tax preparation much easier for us. We use Xero for our accounting needs. It’s integrated with our bank accounts and mortgage software, ensuring every transaction is recorded accurately. One tip I’d recommend is using Xero’s reconciliation feature. It matches our transactions with bank statements, highlighting discrepancies we might miss. During our last tax season, this feature saved us from significant errors and ensured we were compliant with all tax laws.
Austin Rulfs
Founder, SME Business Investor, Property & Finance Specialist, Zanda Wealth
Connect Avalara for Multi-State Compliance
One of the most powerful tax compliance fintech solutions I’ve experienced is through using Avalara to simplify multi-state sales tax compliance. One best practice, for example, is to connect Avalara’s platform to your sales system (for which there are a lot of integrations) to automate the calculation and collection of sales taxes across different states. This automation ensures you’re charging the correct tax rates at the point of sale and keeps you up-to-date with changing tax laws. Avalara can also handle both filing and remittances, reducing the risk of errors and penalties.
Jack Perkins
Founder and CEO, CFO Hub
Automate Taxes with QuickBooks
One tool I’ve personally found incredibly useful for tax preparation is QuickBooks. It automatically tracks expenses, calculates taxes, and updates with the latest tax laws. I’ve found it saves so much time, especially with the reminders for deadlines and alerts when something needs attention. Using QuickBooks has made it much easier to stay compliant and stress-free during tax season.
Dinesh Agarwal
Founder, CEO, RecurPost
Link Fintech Tools to Bank Accounts
Fintech tools are a lifesaver for tax prep! Apps like QuickBooks or Xero can link directly to your bank accounts, automatically track expenses, and organize everything into neat, tax-ready reports. This makes staying on top of compliance a breeze and reduces stress. One tip? Start early—let the tools do the heavy lifting throughout the year so tax season doesn’t sneak up on you. Plus, having everything in one place keeps you prepared for any surprises.
Jared Weitz
Chief Executive Officer, United Capital Source
Connect Payment Processor to Accounting Software
Wave Accounting has been a game-changer for keeping our insurance business tax-compliant while saving time on bookkeeping. When we first started my business, I spent countless weekends catching up on receipts and invoices, but now the app automatically scans and categorizes everything as it comes in. I strongly recommend connecting your payment processor directly to your accounting software—it helped us reduce errors in revenue reporting and made quarterly tax estimates much more accurate.
Gregory Rozdeba
CEO, Dundas Life
Leverage Fintech for Automated Tax Tasks
Small businesses can significantly simplify tax preparation and ensure compliance by leveraging fintech tools like Xero, QuickBooks, or Gusto. These solutions automate essential tasks such as expense tracking, tax categorization, and payroll integration while providing real-time financial insights. They help maintain accurate records and streamline processes to minimize manual errors, ensuring readiness for tax filings or audits.
Best Practice: Regularly reconcile your accounts and take advantage of built-in reporting features to prepare for tax deadlines. Integrating these tools with a professional tax service or consulting a CPA ensures that compliance requirements are met while optimizing deductions. This combination of automation and expert advice enhances financial accuracy and reduces stress during tax season.
Gary Jain
CEO, Ledger Labs
Integrate Bookkeeping and Payments for Real-Time Tax Position
Here’s a challenge: Why do so many businesses treat tax prep like a once-a-year fire drill? The real game-changer is flipping that mindset. Instead of scrambling every April, use fintech tools to make compliance a natural part of your daily operations.
Think about it: Are you using a platform that shows you your tax position in real time? Imagine knowing your quarterly liabilities every single day instead of guessing. Fintech makes that possible with tools that integrate bookkeeping, payments, and even tax estimation into one dashboard. But here’s the key—are you using it in a way that works for you, or are you still stuck adapting to it?
True simplification happens when fintech bridges the gap between operations and compliance. It’s not about automating taxes; it’s about creating systems that keep you compliant without you even thinking about it. What could you do with all that saved time and mental bandwidth?
Ask yourself: Is your current tax process proactive, or are you just surviving? The right fintech setup might not solve everything, but it can definitely help you reclaim your sanity.
Marshall Greenwald
Founder, Ionia
