The Upwork Foundation is shifting its 2026 philanthropic focus towards creating new pathways into work for entry-level professionals and freelancers as artificial intelligence continues to reshape traditional junior roles.
The Foundation, Upwork’s independent philanthropic arm, says the growing use of AI is putting pressure on the entry-level jobs that have traditionally helped young people gain practical experience, develop workplace skills and establish their careers.
Its response is to invest in organisations creating work-based learning opportunities that can give early-career workers the experience and skills they need to enter an increasingly AI-driven labour market.
Fewer traditional entry-level jobs
Entry-level positions have traditionally provided young professionals with opportunities to learn through practical work, including research, drafting, data entry and analysis.
But as generative AI becomes capable of handling more cognitive and analytical tasks, companies may require fewer junior workers for some of these responsibilities.
The Foundation points to data from SignalFire showing that entry-level hiring as a share of total hiring at the 15 largest publicly traded technology companies has fallen by 50% compared with the pre-pandemic period. It also notes declines in entry-level positions across sectors including finance, consulting and accounting.
For young workers, the problem goes beyond finding a first job. Without early-career opportunities, they can struggle to build the demonstrable experience and practical skills employers increasingly expect.
New opportunities for aspiring freelancers
The Foundation's 2026 focus could be particularly relevant to people seeking to build careers outside traditional full-time employment.
Among the models it says could qualify for funding are programmes that prepare professionals for gainful freelance careers.
This could provide aspiring freelancers with structured opportunities to develop skills, gain practical experience and build a track record of work before competing independently in the freelance marketplace.
For someone entering freelancing without an established portfolio or client history, access to work-based learning can help address one of the biggest barriers to starting: the need to demonstrate experience before having an opportunity to gain that experience.
Paid work-based learning takes centre stage
The Foundation plans to evaluate potential grantees based on their experience delivering or enabling paid, work-based learning, their ability to respond to labour-market challenges and their willingness to develop new job-readiness models.
Potentially eligible programmes include:
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Earn-and-learn programmes combining employment with industry credentials
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Paid internships in knowledge-work fields with strong pathways to employment
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Apprenticeships incorporating AI-enabled tools
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Service corps programmes connecting graduates with employers
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Paid founder-shadowing programmes for aspiring entrepreneurs
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Paid gap-year programmes for high school graduates
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Programmes preparing professionals for freelance careers
The emphasis on paid opportunities is significant for early-career workers because it combines skills development with actual work experience rather than requiring young people to accumulate unpaid experience before becoming employable.
AI readiness becomes part of career preparation
The Foundation is also prioritising organisations that integrate AI readiness into their programmes.
For entry-level workers, this could mean learning not only traditional professional skills but also how to use AI-enabled tools in real work environments.
The Foundation's stated approach recognises that AI is changing the nature of work rather than simply eliminating individual jobs. Its 2026 grantmaking therefore seeks models that can help workers adapt to the changing labour market while gaining the practical experience needed to progress.
For freelancers, AI readiness could also become increasingly important as clients look for professionals who can combine specialised expertise with effective use of new technologies.
Why this matters for early-career workers
The Foundation says employers are increasingly placing emphasis on demonstrable skills and experience, rather than relying solely on educational qualifications.
It cites Cengage's 2025 survey, which found that only 44% of employers surveyed considered a college degree a strong indicator of career readiness.
That creates a difficult cycle for young professionals: employers want evidence of skills, but the traditional jobs that provide the opportunity to build that evidence are becoming harder to access.
Work-based learning programmes could help bridge that gap by allowing people to earn, learn and build verifiable experience at the same time.
A potential new route into freelancing
For aspiring freelancers, the Foundation's 2026 strategy could help create an alternative route into knowledge work.
Instead of moving directly from education into a conventional entry-level job, workers could gain experience through internships, apprenticeships, earn-and-learn programmes or structured freelance training.
The goal is to help early-career professionals develop the combination of skills, experience and work history needed to compete for opportunities in the modern labour market.
The Foundation acknowledges that no single organisation can solve the decline in traditional entry-level work. Its objective is instead to support nonprofits that can pilot and scale new work-based learning models capable of creating sustainable pathways into employment.
For freelancers and young professionals, the significance of the initiative lies in its recognition that the path into a career is changing — and that new pathways may be needed to replace the entry-level jobs that once served as the starting point.
Source: Upwork