The future of gig work: From apps to AI to agile workforces

Updated: September 8, 2025

By: Mike Bollinger

7 MIN

Key Takeaways

  • Gig work is entering a new era of regulation and accountability. Governments are moving to classify gig workers more clearly, pushing for fairer pay, algorithm transparency, and portable benefits that redefine what a “gig” really is.
  • AI is disrupting gig roles but creating new ones. While automation may replace many task-based gigs, it will also fuel new demand for human-in-the-loop, creative, and empathy-driven work—shifting value toward what machines can’t do.
  • Internal gigs are becoming a strategic source of skills.
    Once seen as engagement tools or talent pilots, internal gig platforms are becoming a strategic lever in workforce planning, enabling organizations to dynamically source skills, break down silos, and retain talent through meaningful stretch work.

“Reputation is the currency that says you can trust me.” – Rachel Botsman


What is a gig? How a jazz term became the future of work

The word ‘gig’ is commonly thought to have originated as a shortened form of "engagement," referring to a musician's booking or job in the U.S. jazz scene in the early 1900’s. When you hear the word gig today, you might picture a rideshare driver, a delivery person, or a freelancer picking up tasks online. But the term’s journey from jazz clubs to job platforms is as fascinating as it is revealing about how work continues to evolve. And it is no longer uniquely American.

(“Hey, I got a gig!”) From music to the modern labor market

What’s striking is how the gig concept adapted to - and was accelerated by - technology, economic shifts, and changing worker expectations. The 2008 financial crisis pushed many to seek alternative income sources, freelancers began referring to short-term projects as “gigs”, fueling the rise of gig platforms. Similarly, smartphones enabled on-demand work at a scale and speed never before possible. Platforms like Fiverr, Upwork, TaskRabbit, Uber and DoorDash normalized the idea that workers could piece together income through multiple, often temporary, engagements. The term became synonymous with flexible work, whether by choice or necessity.

Importantly, this new gig economy blurred the lines between entrepreneurship and employment, autonomy and insecurity. Gig workers could work where and when they wanted, but often without benefits, predictable income, or long-term stability.

Gigs, guesses, and gut instincts: What’s next?

Look, I don’t have a crystal ball, or even a particularly well-trained AI model whispering predictions in my ear. But I’ve spent enough time squinting at trends, watching policy shifts, and listening to analysts, executives and end users to form a few educated hunches. So here are a few thoughts: equal parts pattern recognition, instinct disguised as trend forecasting, and just enough confidence to write about it.

Prediction #1 - Platform work will face more regulation

Expect a tightening of labor laws around gig work, with greater focus on worker protections: fair pay, benefits, and transparency. The term gig might evolve to imply flexible employment rather than unprotected hustle.

It’s a simple question really …

Are gig workers employees, contractors, entrepreneurs, or something new altogether?

Expect greater regulation and more conflict in the years ahead as governments, companies, and workers grapple with this evolving reality. Key areas of emerging regulation:

  • Worker classification: Several jurisdictions are moving to reclassify certain gig workers as employees rather than independent contractors, entitling them to benefits like minimum wage, overtime, and unemployment insurance.
  • Algorithm transparency: Gig workers are often managed by opaque algorithms determining pay, assignments, and deactivations. Regulators are beginning to demand greater transparency and fairness in how these systems operate.
  • Portable benefits and social protections: One proposed middle path is the creation of portable benefits. This is so gig workers can access health insurance, retirement savings, or paid leave regardless of platform.

Potential implications:

  • Platforms may resist changes that increase costs, threatening the low-margin business models many rely on.
  • Workers may face uncertainty during regulatory transitions, caught between promises of flexibility and the need for security.
  • Governments globally will need to balance innovation, job creation, and worker protection, a complex, politically charged task.

Prediction #2 - AI and automation will reshape gigs

AI is slated to take over many repetitive, rules-based tasks that once formed the backbone of gig work: such as basic data entry, transcription, simple customer service interactions and driving (in the near future, with autonomous vehicles). This means that many gigs we think of today may decline as technology takes over.

But at the same time, AI will create new categories of gig work that are complementary to automation. These could include:

  • Human-in-the-loop roles where workers provide oversight, ethical judgment, or personalization that AI can’t match.
  • AI trainers, and validators who fine-tune AI outputs
  • Creative gigs in design, storytelling, music, and video where human taste and originality remain essential.
  • Community-building, caregiving, and coaching gigs where empathy and relationship-building matter

Potential implications:

  • Rather than eliminating gigs, AI will shift the value toward what is uniquely human, creativity, empathy, judgment, and collaboration, while demanding that gig workers upskill to stay ahead of automation.
  • AI will evaluate gig worker performance in real-time, adjusting access, pricing, and ranking accordingly. Not just from customers, but from the systems themselves.

Prediction #3 - Gigs will come inside the enterprise: the rise of internal gig marketplaces

One of the most exciting shifts is how companies have rapidly adopted internal gig marketplaces. These platforms Cornerstone Talent Marketplace for instance) let employees find short-term projects, stretch assignments, or skill-building opportunities within their organization. It’s not just about productivity; it is also keenly developmental; nothing beats learning by doing. These marketplaces help find those assignments that:

  • Break down silos by matching talent to projects across departments.
  • Shift from task-based to talent-based gigs, employees take ownership of their development.
  • Enable organizations to deploy skills where they’re needed most, fast.
  • Retain people by offering variety, flexibility, and purpose.

Potential implications:

  • In this model, gigs and stretch assignments might blur.
  • Gigs tend to be transactional, whilst stretch assignments are developmental, meant to push someone beyond their comfort zone to build new skills. (employers will embrace both)
  • This has to be about more than driving efficiency for a few extra dollars, they are about building careers inside a company by contributing to meaningful work beyond a job description.

A few bonus predictions

Shift from microtasks and commoditized work (rideshare, deliveries, “clickwork”) to knowledge-based gigs for roles in marketing, design, data science, learning, and even HR, will mean platforms and companies will compete for specialized expertise, not just availability.

Performance monitoring and dynamic pricing will accelerate; we already see this in simple models such as Uber surge pricing

External sourcing will evolve as companies make it a formal part of their workforce planning cycles, not just as stopgap labor but as a strategic choice. Cornerstone has outline how to approach this strategic choice as a part of the 4B framework – Build, Buy, Borrow or Bot.

Blockchain might find new legs in a “reputation wallet” that workers own, smart contracts for gig work, tokenized incentives and global borderless payments. Entering a “boring but useful” phase.

Final Thoughts

The term gig has always carried a mix of freedom and uncertainty. From jazz musicians hustling from club to club, to today’s app-based workers stitching together income, gigs have reflected how technology, culture, and economy shape the way we work. The future gig may be less about tasks on demand and more about building personal brands and micro-businesses, with platforms offering the infrastructure but workers owning the value.

The next chapter of the gig story will depend on how we balance flexibility, fairness, and technology. Increasingly, gigs won’t just happen outside a company’s walls, they’ll happen within them, while offering employees new ways to grow, contribute, and thrive.


Learn more about how to create your internal gig marketplace with Cornerstone Talent Marketplace. Give employees access to cross-functional projects, short-term assignments, and mentorship opportunities that fuel growth, while surfacing the skills and talent pools your organization needs to stay agile and aligned to business priorities, now and next.

The smartest organizations don’t chase talent outside; they unlock it from within.

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