Small Business Software That Actually Helped Me (And Some That Didn’t)
I started a small e-commerce business about four years ago selling specialty coffee equipment. Within the first six months, I was drowning in spreadsheets, losing track of inventory, and doing invoices by hand in Google Docs like some kind of medieval accountant. Something had to change.
Since then I’ve tried a frankly embarrassing number of software tools. Some stuck. Some got abandoned after a week. Here’s what I’ve actually learned about each category — including the stuff nobody mentions in the feature comparison charts.
Accounting and Finance
I started with Wave because it was free. For a solo operation doing maybe 30 transactions a month, it was fine. Invoicing worked, expense tracking was basic but functional, and the price (zero dollars) was extremely right.
When I hired my first employee and started dealing with payroll, Wave wasn’t cutting it anymore. Switched to QuickBooks Online, which is the default answer for a reason — it just handles most of what a small business needs. Bank account syncing, expense categorization, quarterly tax estimates. The interface isn’t beautiful, but it works.
FreshBooks is worth looking at if you’re service-based rather than product-based. A designer friend of mine swears by it for time tracking and client invoicing. Xero is popular with people who want more integration options — it connects to basically everything.
My actual advice: don’t overthink this. Pick one of the big names, use it for three months, and switch if it’s not working. The worst choice is spending six weeks “researching” while your receipts pile up in a shoebox.
CRM (Customer Relationship Management)
I resisted getting a CRM for way too long because it felt like overkill for a small business. Then I lost a $2,000 wholesale lead because I forgot to follow up. That was an expensive lesson.
HubSpot’s free tier is where I started, and honestly it’s where most small businesses should start. You get contact management, deal tracking, and basic email integration without paying anything. The paid tiers add marketing automation and more sophisticated analytics, but the free version handles the fundamentals.
Salesforce is the industry standard but it’s honestly too much for most businesses under 20 employees. The setup alone took a friend of mine weeks. Zoho CRM hits a nice middle ground — more capable than HubSpot free, less overwhelming than Salesforce, and the pricing is reasonable.
The important thing with any CRM is actually using it. A CRM you don’t update is just an expensive address book. I set a rule for myself: every customer interaction gets logged the same day. Not the next morning, not when I have time. That day.
Project Management
Trello for simple stuff. Asana for more complex stuff. That’s really it for most small businesses.
I used Trello for about two years and loved the visual Kanban board approach. Drag cards from “To Do” to “In Progress” to “Done” — satisfying and intuitive. But when projects got complicated with dependencies and multiple team members, the card-based system started feeling limited.
Switched to Asana, which handles task dependencies, timelines, and team workload better. The learning curve is steeper but manageable. Basecamp is worth considering if you want something opinionated about how project management should work — it’s less flexible but also less likely to become a cluttered mess.
Monday.com is popular right now but I found it overly complicated for what I needed. Your mileage may vary.
Point of Sale
If you sell physical products, your POS choice matters more than you think. I went with Square because the hardware was cheap and the setup was simple. Card reader plugged into my phone, and I was processing transactions at a pop-up market that same afternoon.
Square’s inventory tracking is decent for basic needs. Shopify POS is better if you’re also running an online store since everything stays in sync. Toast is specifically designed for restaurants and food service — if that’s your world, it’s worth the premium.
The hidden cost with POS systems is transaction fees. They all charge somewhere between 2.5-3% per swipe. At volume, that adds up fast. Negotiate rates if you can, especially once you’re processing over $10k monthly.
HR and Payroll
When it was just me, payroll was a bank transfer to myself. When I hired two part-time employees, I needed actual software. Gusto was the clear winner for a small operation — it handles payroll, tax filings, benefits, and onboarding. The interface is clean enough that I didn’t need help setting it up.
BambooHR is better if you’re growing toward 20+ employees and need more structured HR workflows. For under 10 people, Gusto does everything you need without the complexity.
Marketing and Email
Mailchimp for email marketing. It’s not the cheapest option anymore since they changed their pricing, but the free tier works for up to 500 contacts and the template builder is genuinely easy to use. I send a monthly newsletter to customers and it takes me about an hour from start to send.
For social media scheduling, I use Buffer. It’s simple — write the post, pick the platforms, schedule the time. Hootsuite does more but also costs more and has a busier interface. For a small business posting a few times a week, Buffer is plenty.
Document Storage and Collaboration
Google Workspace if you’re a Google person. Microsoft 365 if you’re a Microsoft person. Both work fine. I use Google Workspace because the real-time collaboration in Docs and Sheets is excellent and the pricing is reasonable at $6/month per user.
Dropbox Business is worth considering if you deal with large files (video, design assets) since its sync is faster and more reliable in my experience. But for documents, spreadsheets, and presentations, Google or Microsoft are the obvious choices.
Communication
Slack for team messaging. Zoom for video calls. These have basically become the defaults for a reason. We tried Microsoft Teams for a while and it worked fine too — slightly better if you’re already in the Microsoft ecosystem, slightly worse as a standalone tool.
One thing I’ll say: don’t over-tool your communication. Pick one messaging platform, one video platform, and stick with them. Having conversations split across Slack, Teams, email, and text messages is a recipe for missed information and frustration.
Security
This is the category most small businesses ignore until something goes wrong. At minimum, use a password manager (1Password or Bitwarden) and enable two-factor authentication on everything. That alone prevents the majority of small business security incidents.
Beyond that, a basic endpoint protection tool (Bitdefender, Norton, or Malwarebytes) covers most threats. If you handle customer payment data or health information, talk to an actual security professional — the stakes are too high for DIY.
The Real Advice
Don’t try to implement everything at once. Start with the tools that solve your biggest pain point — usually accounting and communication. Add more as you actually need them. The businesses I’ve seen waste the most money on software are the ones that bought a full stack of premium tools before they even knew what they needed.
Most of these tools have free tiers or free trials. Use them. The best software for your business is the one that fits how you actually work, not the one with the most impressive feature list.
