There’s a very real danger in elevating the role of AI in today’s business applications to a hyperbolic level. A mixture of cynicism, fear and topical exhaustion can often overwhelm tech neophytes and obscure the message of what’s possible.
Square 9 Softworks
Then there are companies such as Square 9 Softworks, for whom AI technology has truly amplified the virtues of its intelligent information management platform. President and CEO Stephen Young can attest to what a difference maker AI has been in the past two years alone. In fact, during 2025, Square 9 rolled out the second phase in its AI-driven document processing journey, InquireAI. Its ability to extract information from myriad documents—without the need for traditional optical character recognition and minus some cost and complexities—has been huge for the company and its dealer partners.
In this installment of Getting to Know You, Young shares insights into how AI technology has fueled customer growth as well as Square 9’s approach to nurturing current accounts. He shares perspective on the company’s R&D initiatives and collaborations with heavyweights such as Amazon Web Services to leverage agentic AI, as well as the release of GlobalSearch Go for Square 9’s content management platform. Young feels development and diversification will be key to the company building upon its legacy.
Talk a little about the evolution of Square 9 Softworks and the channels it serves.
YOUNG: This marks our 20th year, having been founded in 2006. Looking back, we began as a simple digital file cabinet for PDFs coming off the MFP. We then evolved into a process automation engine for routing documents, and today we’re an intelligent information management platform, leveraging AI to extract data from documents and feeding it directly into line-of-business applications.
What’s kept Square 9 relevant over two decades is our development-first mindset, but the office equipment channel has transformed significantly as well. When I entered the industry in the predigital era, it was all about putting toner on paper, whether for print or fax. Today, the focus is much broader, centered on meeting customers’ overall technology needs, from managed services to software and beyond.
How would you characterize 2025 from a business standpoint?
YOUNG: It was a strong year for us, largely because of the introduction of AI-driven intelligent document processing. We began laying the groundwork the year before, but 2025 became a true breakthrough, fueling a significant growth surge, particularly in the second half of the year. This momentum contributed to roughly 20% growth in bookings across both our OED ERP partners and direct operations channels.
We added several hundred new customers to the platform, with hundreds more migrating from our on-premises solution to our cloud offering. Overall, it was a very successful year.
What were some of the highlights for your company during the past year? What resonated with you the most?
YOUNG: It really comes down to launching the second phase of our AI-driven intelligent document processing last year. In 2024, we introduced a product called TransformAI which focused on a specific solution—invoice processing—using large language models. It worked well but was very limited in scope. As soon as we released TransformAI, customers immediately asked how they could use the same capabilities for other document-driven processes within their businesses.
That feedback drove our continued R&D and led us to shift in 2025 to a generative AI approach. The simplest way to describe it is that we’ve injected a ChatGPT-like experience into the document workflow to develop InquireAI. This dramatically expanded our capabilities and opened new opportunities for our dealer channel.
We can now extract information from virtually any document—PDFs, screenshots, even cell phone photos—with exceptional reliability. It’s fundamentally changed the approach for us and our resellers by removing much of the cost and complexity associated with reliable data extraction, something that previously depended on traditional OCR. It’s now far easier to implement these processes at scale.
How did you perform within the office technology dealer channel last year, and what were some of the keys to your success?
YOUNG: I think it was a breakthrough year for us. We started off at a typical pace, possibly even a little slower in Q1, but we really focused on making our reseller channel more aware of the opportunities that AI presented. As a result, we saw explosive growth in the second half of the year. While it took a while to launch this second wave of intelligent document processing with InquireAI, once our dealers saw the potential it represented, they were quick to adopt the platform. This included both their internal operations and the needs of their customers. We’re seeing that spill into 2026 as well.
What’s the strategy for growing your dealer base?
YOUNG: We have a mature and highly productive reseller channel, and while we added several new partners last year, our priority is educating and nurturing our existing base. Many of our resellers are performing at high levels, and others have the potential to grow significantly once they fully understand the opportunities available to them.
Every partner I speak with emphasizes the importance of new customer acquisition, and that message was echoed recently by Oscar Sanchez from Kyocera at a resellers kick-off I attended. The focus right now is on capturing market share, strengthening customer retention and growing annual recurring revenue—all areas where our offering directly supports the reseller. Our unique solutions help create differentiation when competing for new business, and the sticky nature of our process automation makes it unlikely for customers to leave upon renewal. We also support retention, and our subscription services are helping dealers build substantial ARR; several even surpassed the million-dollar mark last year.
Ultimately, it’s about evangelizing this message and helping dealers recognize how much has changed in just the last year or two.
How do you see AI playing an even greater role moving forward within your product offerings?
YOUNG: Without a doubt, AI extraction has enabled us to feed critical business systems, such as customers’ ERP and CRM platforms, with the data they need to operate effectively. We can now do this with far greater accuracy and efficiency than manual entry, which has reshaped our industry and made information management more appealing to new markets. As AI continues to evolve rapidly, it will keep influencing the direction of intelligent information management.
We’re actively engaged in R&D with AI platform developers such as AWS to explore the use of agentic AI within our platform. Machines can now communicate intelligently with one another, and we see simplified integrations as an important next step. Greater access to information also supports improved reporting and predictive modeling for business processes. These are key areas driving our current R&D efforts.
What does the future hold for Square 9 in terms of new product development? Is there anything in the works from a partnership/integration standpoint?
YOUNG: Development is continuous at Square 9; it’s how we’ve stayed relevant for 20 years. We continue to invest heavily in R&D, especially in expanding our AI capabilities. Last year, we launched GlobalSearch Go for our content management platform. It’s a hosted interface that delivers a faster, more powerful user experience and enables real-time updates instead of formal upgrade cycles. We’ll keep expanding this platform into areas such as capture and web forms management as part of this year’s initiatives.
From a channel perspective, we remain focused on the office equipment space and recently launched a new partnership with Visual Edge Information Technology, whose national representation is a major advantage. We’ve also diversified our channel to include ERP providers, which has become a strong growth area for us. Our efforts center on organizations representing Microsoft Dynamics 365, NetSuite and Sage, among others, and this segment continues to grow rapidly.
We believe the generative approach to IDP not only delivers better results than competitive products, but also offers far more flexibility for our dealers and their customers.
– Stephen Young, Square 9 Softworks
AI has also driven significant traction as organizations look to feed their business applications with the data we extract. While we’ve always been capture-focused, IDP is becoming an increasingly important part of our offering.
How does Square 9 differentiate from the competition in a hotly contested market?
YOUNG: Our greatest differentiator has always been our strength in document and information capture. From the beginning, we’ve focused on this; structured or unstructured data extraction, and our web forms designer, which we believe is unparalleled in the industry and drives efficiency through business process automation platforms. This remains a core strength with the introduction of InquireAI and intelligent document processing.
We believe the generative approach to IDP not only delivers better results than competitive products, but also offers far more flexibility for our dealers and their customers. It enables them to solve a wider range of customer challenges through a simplified method: just asking for the information they need in natural language.
Based on everything we’ve seen so far, no other product in our space has matched these results or this approach. It’s a capability we’re very bullish on and one we believe gives us a clear competitive advantage.
What will be the keys to growth moving forward?
YOUNG: To continue our strong growth, we need ongoing development and diversification. Two years ago, 75% of our net-new customers came from accounts payable automation. Our early AI model was limited to invoices, but it delivered measurable ROI, long-term success and strong dealer stickiness. That focus served us well, but generative AI’s ability to extract data from a broad range of documents has opened significant new opportunities.
Even within the office of the CFO, InquireAI now supports sales and purchase order processing, using extracted data to automate invoice creation—the reverse of a payable invoice. We’ve also expanded into bills of lading, arrival notices and other logistics documents. Beyond the CFO’s office, we’re seeing growth in areas where data extraction was once difficult or impossible, such as claims processing and industrial documents with complex tables and formats. These are now not only achievable but tasks we handle on a near-daily basis.
New opportunities continue to emerge, and we’ll keep developing the platform to support expansion across more areas of our customers’ businesses. Diversification remains essential.
What are your company’s goals for the next 12 months, and what will success look like in your eyes?
YOUNG: To achieve the success we’re aiming for, we need to spend the next 12 months better educating our channel on the new possibilities available to them. Many dealers still think of Square 9 as the company we were 5 or 10 years ago, not who we are today. With AI evolving rapidly, keeping our community informed about how these advancements benefit them has been a top priority.
Dealers want the best ways to serve their customers, and if we’re not clearly communicating the value of this fast-changing space, we’re not doing our job. We ended last year very strong, and that momentum carried into this year. With 20% overall growth last year and a 124% surge in January 2026 bookings alone, we are off to a tremendous start. Some of that was carryover, and we’re forecasting a very strong Q1 to open our fiscal year. While our original 2026 plan targeted 20% growth, we’re already discussing raising that bar based on early trends.
Ultimately, our success in 2026 will be defined by how effectively we communicate the possibilities of this rapidly changing market to our channel and help them share in the proven results we’re seeing.
