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This Week’s Small Business Technology News: Ads Coming For Chat GPT And 10 Free Windows Apps For Productivity

By December 28, 2025No Comments

(This column originally appeared in Forbes)

Here are five things in small business technology that happened this week and how they affect your business. Did you miss them?

This Week in Small Business Tech News

Small Business Technology News #1 — ChatGPT ‘to roll out advertising in 2026’ sparking major issues for Google.

ChatGPT is expected to introduce advertising inside conversations starting in 2026. This marks a major shift toward conversational discovery, where people get answers — and soon, ads — directly through dialogue rather than traditional search results. According to the article, this upcoming feature could possibly undo Google’s dominance as the top search engine as conversational AI has “gone mainstream” in less than three years. Because ChatGPT understands context and intent, conversational ads feel more personal. Google has increased its AI overview results through Gemini but click-on ads are reduced. ChatGPT’s conversational ads will be woven into the conversation rather than direct links. Going forward marketers will need to evolve from SEO to AI optimization/conversational formats. (Source: ITP.NET)

Why this is important for your small business:

This was inevitable and can’t come too soon. Google has dominated the online advertising space for years, making it harder for small businesses and those with smaller pocketbooks to get their products and services noticed. Finally — and thanks to AI chatbots — there’s now a legitimate competitor to this monopoly. And it won’t be just OpenAI playing this game. In the end this will provide more affordable and a greater number of options for your business to advertise online.

Small Business Technology News #2 — Insightly introduces AI into its CRM platform.

Insightly has rolled out Copilot — an AI chatbot designed to make CRM usage more intuitive and significantly more powerful. The goal is to help teams automate work, clean data, and provide insights simply by asking the system what they need. Copilot will allow users to create tasks, update records and retrieve customer data through conversational task management. The chatbot is programmed to clean and correct CRM data to maintain a high-level of accuracy. Copilot’s insight generation will identify priority leads, follow-up opportunities, and key customer trends. Insightly argues that most teams use only a small fraction of their CRM’s features. Copilot is meant to change that by acting as a “companion” that keeps deals and customer relationships organized and visible — and aims to boost adoption across sales, marketing and customer success. (Source: TechRadar)

Why this is important for your small business:

Insightly is an excellent CRM application that I mention as a worthy competitor to others that my firm implements. And Insightly has an opportunity. That’s because, at least so far, my experience with the AI functionality introduced by CRM platforms has been underwhelming. But that doesn’t mean that they won’t be important — and reliable — as they mature. Insightly’s introduction of its Copilot AI will certainly be welcomed by its customer base and hopefully is just the beginning of business-ready AI tools that CRM platforms will be rolling that actually help us improve our productivity.

Small Business Technology News #3 — Squarespace introduces pay links to help small businesses get paid faster.

Squarespace has introduced Pay Links — a simple way for small businesses and solo entrepreneurs to collect payments online using a dedicated URL — with no online store or shopping cart required.. (Source: Squarespace)

Why this is important for your small business:

According to the company, Pay Links allows businesses to accept payments through text messages, social media, QR codes or embedded website links. They’re designed to be fast, secure, branded, and easy to share anywhere customers already interact with the business. The app is especially of interest for service‑based entrepreneurs, including consultants, coaches, and photographers and for merchants who can accept individual payments without having to rely on an online store or cart.

Small Business Technology News #4 — Zendesk acquires a search platform.

Zendesk announced that it has acquired Unleash — an AI-powered enterprise search platform — to strengthen its customer service and internal support capabilities. The goal is to give employees and service teams fast, secure, and unified access to company knowledge across all internal systems. Unleash solves this by connecting to 70+ data sources and providing a single, AI-driven search layer. Capabilities also include a permission-based retrieval system ensuring that employees can only access information they’re authorized to use, reducing the risk of data leakage; and AI-powered intent analysis to understand queries, allowing teams to respond faster with contextual knowledge. (Source: CX Today)

Why this is important for your small business:

I’m a fan of Zendesk because the platform is perfectly positioned to help smaller companies provide a higher level of customer service rivalling larger CX systems. I’m guessing this move was made to allow searching over a greater number of inter-connected systems outside of just the Zendesk database which makes sense. For Zendesk customers it will be important that this new product is quickly integrated and made seamless.

Small Business Technology News #5 –10 free Windows apps a tech write says improved his productivity.

Jack Wallen of ZDNet highlighted ten open‑source, no‑cost Windows applications that significantly improve his productivity across tasks like writing, automation, backups, and AI use. His recommended apps include: LibreOffice, Wallen’s “go-to office suite” that includes all the standard office tools (word processor, spreadsheet, presentations and database) and is customizable, Flow Launcher, a fast, keyboard‑driven app launcher and file search tool and File Converter, which adds a right‑click menu option to convert or compress files (audio, video, images, documents). (Source: ZDNet)

Why this is important for your small business:

It’s a great list and a reminder that there are plenty of free tools available that can help our employees get their jobs done faster that don’t necessarily involve AI.

Each week I round up five business technology news stories and explain why they’re important for your business. If you have any interesting stories, please post to my X account @genemarks

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