How SideQuest Automation Simplifies Purchase Order Workflows for SMBs

The idea for SideQuest came from seeing the same problem over and over again while working with distributors. Purchase orders were coming into inboxes as PDFs, Excel files, and emails, and someone on the team had to manually read them, find the customer, match every product to the correct item in QuickBooks, and then retype everything into an estimate or order. It was repetitive, time-consuming, and incredibly easy to make mistakes. What really bothered me was that this wasn’t a complicated problem. The information was already there. Businesses were just paying people to move it from one system to another. I started thinking, “Why isn’t something just doing this automatically?” That frustration became the foundation for SideQuest. I wanted to build something simple that could read a purchase order, understand what the customer wanted, match it against the company’s existing catalog, and create the estimate automatically. No giant implementation, no massive software project, just automation that actually saves someone time.

The growth tactic that has worked best has been talking directly to the people experiencing the problem and showing them exactly what the product does. Instead of trying to explain SideQuest with a long list of AI features, I can take a real purchase order and show how it goes from an email attachment to a draft estimate. That makes the value immediately obvious. The tactic that completely flopped was trying to make the product appeal to everyone. I initially thought more industries and more use cases would create a bigger market. In reality, it made the messaging weaker. If you tell everyone your product can automate anything, nobody knows exactly why they need it. I learned that being extremely specific about the problem is much more powerful. The best growth conversations have been with businesses where I can immediately say, “You’re probably doing this manually today, and this can eliminate most of that work.“

The biggest complaint is usually that automation sounds great until someone has to actually set it up. Businesses are already dealing with multiple systems, messy product catalogs, inconsistent customer information, and years of accumulated data. The last thing they want is another complicated software implementation. I’ve handled that by focusing heavily on simplicity. SideQuest is designed around the systems businesses already use instead of asking them to completely change their workflow. The goal is to make the first experience extremely straightforward, connect the system, give SideQuest the information it needs, and let it start doing the repetitive work. I’ve also learned that people care less about the technology behind the product than they do about whether it actually saves them time. So rather than selling “AI,” I focus on the outcome. If someone is spending two hours every morning entering purchase orders, the conversation becomes very simple, how much of that work can we eliminate, and how quickly can we get you there?

I think people dramatically underestimate how much manual work still exists inside small and midsized businesses. There is a tendency to assume that if a company is using software like QuickBooks, Shopify, an ERP, or a CRM, everything must already be automated. In reality, there are still countless processes happening through email, spreadsheets, PDFs, copy and paste, and someone’s memory. The software exists, but the systems often don’t communicate well enough to eliminate the manual work between them. That creates an interesting opportunity. You don’t necessarily need to replace the company’s existing software. Sometimes the biggest opportunity is simply automating the repetitive work happening between those systems. I also think people get AI wrong in this market. Businesses don’t necessarily want another AI chatbot or a flashy demo. They want something that quietly takes work off someone’s plate. If AI can save an employee hours every week without forcing the business to completely change how it operates, that is where the real value is.

Over the next 6–12 months, the focus is on making SideQuest smarter, easier to use, and capable of handling more of the workflow automatically. The goal isn’t simply to make the AI more impressive. It’s to reduce the amount of human involvement required from the moment a purchase order arrives to the point where the order or estimate is ready to go. I want SideQuest to become more intelligent about matching products, understanding customer-specific requirements, catching potential errors, and communicating with customers. I also want to expand beyond purchase order automation into additional back-office workflows where businesses are still spending hours doing repetitive administrative work. The long-term vision is for SideQuest to become the layer that connects those everyday processes and quietly handles the work in the background.

SideQuest is currently bootstrapped, fully built, and tested, with the core automation workflow working end-to-end for QuickBooks.

I wasn’t starting from scratch. I had spent more than a decade working in sales, with a significant portion of that time selling technology to distributors, manufacturers, and other businesses with complex operational workflows. I had spent years talking to companies about their processes, their ERP systems, their sales teams, and the problems that slowed them down. That experience gave me a front-row seat to how much manual work happens behind the scenes. I also had experience selling and working with e-commerce and B2B technology, so I understood both the business side and many of the systems these companies rely on. SideQuest came from seeing a problem repeatedly rather than coming up with an idea in isolation. I’m not a career software engineer, but I understood the customer, the workflow, the pain point, and what the product needed to accomplish. That perspective helped me build around an actual business problem instead of simply trying to find a use for new technology.

My biggest mistake was spending too much time building before doing enough validation. Because I understood the problem personally, I assumed I already knew exactly what the product needed to look like. That made it easy to fall into the trap of adding features because they seemed useful rather than because customers were specifically asking for them. I learned that building software and building a business are two completely different things. You can have a working product and still have no real business if the problem isn’t painful enough or the customer isn’t willing to pay for the solution. Now I think much more about validation, distribution, and willingness to pay before building anything new. The product should follow the customer problem, not the other way around. I’d rather have a simple product that solves one painful problem extremely well than a massive product with twenty features that nobody actually needs.