Small Business Technology News Roundup: IBM Shares Crash, ChatGPT To Replace Wall Street Analysts

Why this is important for your small business:

It’s interesting just how long IBM has lasted – and adapted – when you consider how much technology has changed over the decades that the company has been around. Given that history, I wouldn’t bet against the company. But that doesn’t mean that there aren’t significant challenges ahead for it as more companies move to cloud based AI leveraged solutions that hosted and implemented by others. As the Forbes articles says, going forward, companies like IBM will need to keep track of where organizations are investing their technology resources and come up with strategies to keep pace. It’s a lesson for both big and small organizations.

OpenAI Job Listing Suggests ChatGPT Could Someday Replace Junior Analysts at Goldman Sachs

The latest AI vs. jobs piece of news comes from OpenAI after its recent post “Subject Matter Expert, Investment Banking.” The company is seeking an experienced investment banker to help define what high-quality AI-assisted banking work should look like. Responsibilities include: Creating realistic investment banking tasks and evaluations, producing high-quality reference analyses and financial models, and identifying where AI succeeds and fails on banking workflows – just to name a few. Examining the wording of OpenAI’s post, it could be taken as a forewarning that ChatGPT will eventually reduce headcounts among investment bankers. However, it seems the longer-term goal is to have ChatGPT move beyond answering financial questions and become an active assistant for investment bankers – not replace them altogether. In the meantime, speculations will continue. (Source: The Register)

I wrote about this a few years ago and the trend continues. Wall Street firms are investing heavily in AI not only to better serve their clients and get deals done faster and more accurately but to also minimize their headcount. Why hire a junior analyst when AI can do the work of hundreds? And it’s not just Wall Street. Countless firms in the financial services industry are leaning towards more AI solutions to increase productivity and – let’s face it – minimize overhead.

Upwork Releases 2026 Future Workforce Index, Finding AI is Reshaping Freelance Work and Earnings

Freelance networking platform Upwork has released “The Future Workforce Index 2026” which has found that AI is increasing demand for highly skilled independent professionals. The research shows that freelancers on Upwork’s marketplace who use AI earn 34 percent more per hour than those who don’t. According to the data, skilled freelancers make up 38 percent of “U.S. knowledge workers” (up from last year) and demand for generative AI and AI creative projects has surged. The research points out that not all AI work is gaining value with per-contract earnings for generative AI showing a 13 percent decline. (Source: Quiver Quantitative)

According to the news one of the key observations from Upwork’s report is AI adoption will increasingly depend on integrating human expertise – while also creating a growing divide between commodity AI tasks and higher-value, judgment-based work, which draws higher earnings. AI tools is already creating a new generation of freelance entrepreneurs, led by tech and development experts to maximize the use of these tools at their mainly SMB clients.

Windows 11's Latest Update Will Let You Pause Updates Indefinitely

Sean Endicott of Windows Central reported on Windows 11 July 2026 Patch Tuesday update that will allow users to indefinitely pause updates up to 35 days – then simply renew the pause before it expires, allowing updates to be deferred for as long as users choose. Previously, Windows required users to install pending updates before allowing another pause period. The new system removes that limitation. The July update also includes improvements to the Point-in-Time Restore feature, improved widgets, and accessibility enhancements – just a few more than 10 updated features Endicott lists as he declares this as one of Windows “biggest updates of the year.” (Source: Windows Central)

In addition to Microsoft’s reigning in of AI that I wrote about last week, this news further underscores the software giant’s efforts to give back more control to humans, even when it comes to implementing its updates. But be careful – Windows updates are critical for security. I wouldn’t advise my clients to hold back on installing.

Expensify Launches Consolidated Travel Billing to Simplify How Companies Pay for Business Travel

Expense management platform Expensify announced a new option in their Expensify Travel booking platform: Consolidated Travel Billing. The feature allows businesses to pay for all employee travel through one centralized monthly bill, removing the confusion of issuing corporate credit cards to every traveler or reimbursing employees after trips. Companies can pay for flights, hotels, rental cars, and rail travel booked through Expensify Travel using a single monthly invoice – eliminating the extra task of gathering employee out-of-pocket travel expenses. It also offers detailed statements showing trips, travelers, merchants, booking information, and a dashboard that displays all activity, available credit, settlement settings, and more. (Source: Business Wire)

Expensify has long been a leader in automating the capture, recording and analyzing travel expenses and it’s a critical application for any business – big or small – with teams of people that regularly travel. Using expense management platforms like this businesses have proven that they save time and effort. These new features should make those productivity gains even more impactful.

Note: Have a technology story that small business owners should know about? Don’t mind me sharing my opinion? Share it with me on X @genemarks.