AI in hiring and the new freelance economy

Keith Shaw: With the rise of AI tools in almost every aspect of life, those who rely on contracting or freelance work have had to adapt their skill sets in real time.

On this episode of Today in Tech, we’ll look at the future of freelancers and how companies are using AI to hire them. Hi everybody, welcome to Today in Tech. I’m Keith Shaw.

Joining me on the show today is Dave Bottoms, Senior Vice President and General Manager of Marketplace at Upwork.

Dave Bottoms: Thanks for having me, Keith.

Keith: Upwork is all about hiring and freelancing, so I want to get into that. But first, just as a quick way to get to know you: what’s the biggest change you’ve seen in the past year with the rise of AI?

Generative AI has been around for three or four years, but what stands out in 2024?

Dave: One of the biggest changes is demand for people with skills in using tools and prompting agents to do work on their behalf. We’re seeing a lot more demand for those kinds of skills on our platform.

Keith: As companies hire freelancers, are you seeing a rise in roles specifically focused on AI — like prompt engineering, model training, AI integration — or is AI knowledge simply being added into every role?

Dave: It touches many categories on our platform. We see demand for roles like model training, data annotation, and AI integration. Even non-AI roles increasingly list AI familiarity as a plus. Prompt engineering alone has seen more than a 50% year-over-year increase.

Overall, AI-related job postings are up more than 30% year-over-year in Q2.

Keith: Are there certain AI skills that clients value more than others, or is it all over the place?

Dave: It’s across many categories and depends on the job and tools used — everything from general LLM skills with ChatGPT and Gemini to coding tools like Cursor and Replit.

Keith: One concern about freelancing is that AI could replace roles like writers or entry-level coders. Do you see those jobs dwindling?

Dave: AI tools are very good for volume but not as strong for creativity. Humans are still needed to prompt AI effectively. Roles may be shifting toward editing rather than writing, with humans ensuring creativity, quality, and tone. For example, AI translation can miss local colloquialisms that humans catch.

We see more of a pairing between AI and humans, with freelancers as creative editors and quality controllers.

Keith: I recently tested ChatGPT on one of my own LinkedIn articles. It rewrote it in ways that didn’t match my style or humor. In the end, I trusted my instincts as a writer and editor. So you’re right — it’s not quite there yet on creativity, especially with humor.

But are freelancers themselves using AI to enhance their productivity, or are they resisting it?

Dave: Freelancers are early adopters of AI tools. They use them to brainstorm, draft outlines, create summaries, and translate content more quickly. More than half of freelancers on our platform report being advanced or expert in some AI tool. AI makes them more productive and efficient.

Keith: Do clients now expect freelancers to use AI so they can finish projects faster? How does that affect pricing — when a client might think, “Why should I pay for three days of work if ChatGPT can do it in 10 seconds?”

Dave: Anecdotally, freelancers feel AI makes them more competitive. They can work faster while maintaining quality, take on more projects simultaneously, and strengthen client relationships by delivering high-quality work more efficiently.

Keith: So you’re bullish on the future of freelancing? Dave: Absolutely.

Companies of all sizes want flexibility, efficiency, and diversity in their workforce. Freelancers who use AI tools productively are in higher demand, not less.

Keith: How can freelancers “AI-proof” their careers? Should they highlight uniquely human skills, or emphasize AI expertise?

Dave: Freelancers are marketers of their own skills. They should constantly learn, experiment, and gain certifications with relevant tools. Human judgment and creativity can’t be replaced, and delivering quality work builds their reputation. Staying AI-savvy is essential to remain competitive.

Keith: Let’s switch gears to AI in the hiring process. Upwork and other companies are using AI for initial interviews. At first, I was skeptical, but I can see the benefits. How does it work, and how does it help freelancers?

Dave: In July, we began experimenting with “instant interviews” powered by Uma, our AI companion. Clients can ask standard or custom questions, and Uma scores and compares responses. For clients, it speeds up hiring by narrowing down candidates.

For freelancers, it’s a way to showcase communication and collaboration skills beyond a written proposal.

Keith: So it also speeds up the process for freelancers, getting them contracts faster? Dave: Exactly.

Some freelancers even want to feature their interviews on their profiles to prove they’re articulate and trustworthy.

Keith: Can freelancers practice with AI interviews? I’d pay for that feature.

Dave: That’s coming soon. We see value in practice interviews across different categories, with freelancers using excerpts on their profiles as marketing tools.

Keith: Have you seen risks with AI interviews — concerns from freelancers or clients?

Dave: The main concern is volume. Typical job posts can get 20+ proposals. AI helps narrow that down. We’ve seen minor technical issues, but so far, no adverse reactions. We continue to gather UX feedback.

Keith: Hiring with AI also raises issues of bias and errors. How are safeguards built in?

Dave: At Upwork, we follow mindful AI principles: being human-centered, transparent, and accountable. Uma is built and tuned on proprietary data to reduce bias and keep results fair and safe. Transparency is key — freelancers know they’re being interviewed by AI. Keith: Good.

Transparency matters. But in the future, could we see freelancers sending AI avatars to do interviews, while companies use their own AI agents to interview them? Dave: Possibly.

We already see experiments with AI avatars. In the near future, AI agents could pitch and interview on behalf of freelancers and clients, acting as brokers.

Keith: Are freelancers themselves using AI tools during interviews, such as real-time translation or scripting answers?

Dave: Deepfakes are a challenge across the industry, but many freelancers use AI in positive ways — prepping answers, practicing interviews, or improving their communication. Smart candidates use AI to be better prepared, and that helps them win work.

Keith: Does using AI for prep seem dishonest, or is it simply smart preparation? Dave: It depends.

For coding, real-time AI-generated code without disclosure is an issue. But demonstrating proficiency with tools is a positive. For writing or translation, blending AI efficiency with human creativity is the best approach.

Keith: Looking at Upwork’s data, do you see industries moving toward a future where knowledge workers use AI agents to handle most projects?

Dave: The first big wave was distributed workforces. The next wave is human plus AI. Agents won’t replace humans; they’ll support them. Humans will still prompt, guide, and check the work. The sweet spot is human creativity paired with AI efficiency.

Keith: Some companies claim AI teammates will replace workers, but customers often cut jobs instead of blending humans with AI. Do we just need more proof that AI-only work is lower quality? Dave: Exactly.

Human judgment and creativity remain irreplaceable. The future is humans orchestrating agents and tools to complete tasks effectively.

Keith: How long will it take for companies to adopt this “next level” of AI-human collaboration?

Dave: Larger enterprises with complex systems will take longer. But small and midsize businesses are already hiring based on outcomes — like apps, websites, or translations — rather than headcount. Freelancers who use AI effectively to deliver outcomes faster will lead this trend.

Keith: Dave, great insights. Thanks again for joining me on the show.

Dave: Thank you, Keith. A pleasure to be here.

Keith: That’s all the time we have for this week’s episode. Be sure to like the video, subscribe to the channel, and leave your thoughts below if you’re watching on YouTube. Join us every week for new episodes of Today in Tech. I’m Keith Shaw — thanks for watching.