Somewhere in Nairobi in 2022, a young graphic designer was building her life, brick by brick, thanks to a Fiverr profile, a portfolio, and a client list that formed the foundation of her creative career.
She had no way of knowing that the tool about to make her entry-level work obsolete had not been invented yet. Most disruptions come with a warning, a market shift, and a few quarters of bad earnings before the obvious becomes official. This one did not.
ChatGPT launched in November 2022, and within 18 months, billion-dollar companies were issuing profit warnings, creative industries were in free-fall, and that designer in Nairobi was competing not with other designers but with a prompt.
Ask Jeeves shutting down on May 1, 2026, gave the moment a face, a name, and a symbol of an era AI made obsolete. Jeeves was, however, far from alone.
In this article is a partial accounting of who and what the new intelligence economy has already consumed, and what it means if you are building a career, a business, or a livelihood right now.
The jobs that used to be the starting point, the ones that let you build a portfolio and pay rent while you figured out your career, are disappearing before a generation that needed them most has had the chance to use them.
Chegg
At peak value, Chegg was worth $14 billion. Now, it’s barely breathing.
Chegg was the largest education technology company in the US, built on a simple, durable idea where students pay a monthly fee to access a library of pre-solved homework problems and on-demand tutoring.
It worked for years, right up until ChatGPT arrived in late 2022 and did the same thing for free.
Chegg became the first publicly listed company to formally acknowledge AI-induced revenue damage. Its stock fell 48% in a single day in May 2023, and it never recovered.
By late 2024, the market cap had collapsed from $14 billion to under $200 million. For every campus student currently using ChatGPT to get through their homework, there is a company that once charged for that service and is now essentially extinct.
Fiverr and The Freelance Economy
The platform that once employed a generation of creatives is now cutting its own staff to go AI-first.
Fiverr was the marketplace where a graphic designer based in Nairobi could sell a logo to a startup in Berlin, or a copywriter could service clients in another continent without leaving their house.
It was, for many users, the most accessible entry into the global economy.
READ: Upwork Connects and Taxation: What Kenyan Freelancers Need to Know
In September 2025, Fiverr cut 30% of its own workforce while simultaneously deploying AI tools, including ChatGPT-powered writing assistants and Midjourney-based image generation, that now automate the services its freelancers used to provide.
The most cruel part is that Fiverr had spent years telling its own employees to embrace AI, then used that same AI to eliminate their jobs.
Basic writing on freelance platforms is down 21%; basic translation, down 28%; data entry, down 35%.
The World Bank recorded roughly 130% growth in Sub-Saharan African job postings on freelance platforms between 2023 and 2025, but most of that growth was concentrated in AI-adjacent skills. The entry-level work that used to fund the learning curve is gone.
Graphic Design and Visual Creative Work
Graphic design was seen as a career that offered creative freedom and global reach. It’s why people enrolled in design programs, built Behance portfolios, and took on small branding jobs to pay rent as they grew.
Midjourney, Adobe Firefly, DALL-E, and Canva’s AI suite have collectively restructured the economics of that career. A logo that once took a junior designer a day to produce can now be generated in seconds.
READ: Canva Acquires Cavalry and MangoAI to Close Gap With Adobe
A social media content calendar that required a creative team now takes one person with a prompt and less than an hour. Nearly 70% of global marketing and creative leaders surveyed by Canva reported worrying about AI-related job losses in their industry.
The work has not disappeared entirely, but the volume of entry-level, production-based design work that sustained an entire generation of emerging creatives has shrunk dramatically and it is likely not coming back.
Stock Photography
Stock photography was a $5 billion industry that is now merging just to survive.
For decades, photographers across the world sold licensed images to brands, agencies, and publishers through Getty Images and Shutterstock.
By early 2025, tools like Adobe Firefly, Midjourney, and DALL-E were producing billions of AI-generated images per month. Firefly alone had created 3 billion images within months of launch, more than the total archived catalogues of most traditional photo libraries.
Getty’s core creative image segment declined nearly 5% in 2024. The two giants announced a $3.7 billion merger in January 2025, essentially combining their archives to survive the competition.
The generic, serviceable image, the kind that used to pay a photographer’s bills, can now be produced by anyone with a sentence and 10 seconds.
Google Search, Online Publishers and Digital Media
Google is not on this list as a victim. It is on this list because of what its AI pivot is doing to everyone else.
Google’s AI Overviews feature, which generates answers directly on the search results page, has quietly dismantled the traffic model that digital publishers, bloggers, and content creators globally spent years building.
The user never leaves Google; thus, the publisher never gets the clicks. HubSpot lost between 70-80% of its organic traffic in under a year. Business Insider lost 55% between 2022 and 2025 and cut 21% of its staff. Meanwhile, Google still kept its billion users.
For digital publications and independent writers who rely on search to build an audience, this is not a distant trend but a direct threat to the business model that has supported independent online journalism.
Customer Service
One of the most accessible formal employment sectors in Sub-Saharan Africa is becoming systematically automated.
Call center work was never glamorous, but it was real, accessible, and entry-level employment that paid regularly and built professional skills. In Kenya, the sector employed tens of thousands across Nairobi and other urban centers.
Over 80,000 customer service positions were cut in the US alone between 2022 and 2024 as AI chatbots absorbed the workload. Salesforce eliminated 4,000 support roles in a single announcement.
READ: Sama to Lay Off 1,100 Workers in Kenya After Meta Contract Ends
The pattern is global, and the automation technology does not distinguish between markets. The chatbot that replaced a customer service agent in Dallas works just as well for a company in Nairobi, which means the same structural pressure is building across the region.
Junior Developers
For the better part of a decade, learning to code was the advice. Bootcamps sold it and universities pivoted entire departments around it.
In Kenya, a generation of young developers built careers on the promise that software skills were recession-proof and globally portable.
That promise has been quietly revised. Tools like GitHub Copilot, Cursor, and Claude Code now write, debug, and refactor code autonomously, doing in minutes what used to justify hiring a junior developer for 6 months.
Employment among software developers aged 22 to 25 fell nearly 20% between 2022 and 2025.
READ: Microsoft Slashes 9,100 Jobs in Biggest Layoffs Since 2023
Now, 70% of hiring managers believe AI can do the jobs of interns, and 57% say they trust AI output more than the work of a recent graduate.
Senior developers are largely fine, but the bottom of the ladder, the entry point every senior once stood on, has been removed. For a continent producing its largest ever cohort of tech graduates, the timing could not be worse.
What’s interesting is that none of these companies were caught sleeping. Chegg, in fact, partnered with OpenAI. Getty licensed its entire image library to AI companies. Fiverr built its own AI tools and called them the future.
In the first three months of 2026 alone, an estimated 70,000 tech workers globally lost their jobs, more than double the same period in 2025.
The question for Kenya, and for the world more broadly, is not whether AI is coming. It is already here, it already has a body count, and it is not waiting for anyone to finish adjusting.
The question is which skills, which sectors, and which young professionals will be on the right side of the line when the next round of the ledger opens.
