The traditional two-sided marketplace is evolving into an AI-powered octagon in 2025. A few thoughtbot clients with deep marketplace experience share their insights and experiences in this rapidly innovating space.

Going beyond basic caregiving matching

“The marketplace is not a novel concept. It starts with ‘can we bring buyers and sellers together,” said Jon Levinson, co-founder and CEO of Clara, a senior care platform that helps families find affordable, quality caregivers, and a thoughtbot client. “Now the question is how else can we add value, how does our position allow us to provide additional services?”

Levinson was working at Uber when he needed to find care for his ailing father. His family found the experience so challenging that he realized there was a business opportunity there: to connect families in need with quality, reliable caregivers. He worked with thoughtbot to build the first version of his product, and continues to work with thoughtbot now to evolve as Clara grows from serving California to serving more states across the U.S.

He soon realized, though, that simply making a connection between client and customer would be too small of a service to support an entire company. After all, once they were connected, what would they need his marketplace for any more?

The Clara team injected AI into the selection process, using it to make better matches between families and the caregivers they needed. Clara also introduced an emergency no-show program. If a caregiver can’t make a designated appointment, another caregiver can replace them at the same time, another service powered by AI.

More importantly, Clara focused its efforts on the payroll and other needs of their clients. The platform helps them stay in compliance with payroll regulations, pay taxes correctly, ensure caregivers are paid on a regular cadence, and even build their credit scores, in addition to serving as a lead generator for caregivers.

In the future, Clara hopes to add a mobile experience entirely focused on caregivers, to allow them to monitor their business needs while they move from client to client.

Solving supply-side complexity in hospitality

AI is making incredibly complex business processes less costly and easier to develop, said Kate Adamson, co-founder of Folio, an emerging marketplace that connects hotels to suppliers – and helps suppliers find hotels in need of products and experiences.

“Where we’ve seen marketplaces fail is on the demand side,” she said. “If buying is not happening then suppliers don’t participate. Our goal is to onboard hotels first.”

Supplying to hotels has grown increasingly complex as hotels build brand requirements for certain products and participate in group purchasing. Branded hotels must provide the same shower products and sheets in every location, for example. This is where AI can help match suppliers to hotels around particular opportunities that don’t infringe on those requirements.

“This is where AI gets exciting,” Adamson said. “When the complexities are especially challenging, this where natural language processing across a lot of information and constraints, in real-time, matters. That may not have been possible in the past.”

Building stickier platforms with AI and smarter data

AI is super-powering everything that can be done on a marketplace, said Jed Carlson, former CEO of Adwerx, an advertising marketplace for real estate agents and thoughtbot client. “What’s been startling to me is that AI is as good as anything I’ve ever seen humans do, in terms of its ability to improve your content, to use more data sources. AI can hack your brain at an entirely new level.”

The idea for Adwerx extended from Carlson’s previous company, ReverbNation. ReverbNation connected performers with venues, while also providing added services to artists such as profiles and promotional tools.

Adwerx was spun out of ReverbNation, which was ultimately sold in 2021., At Adwerx, Carlson applied the model to the real estate market, building a suite of tools to allow realtors to “promote themselves like rock stars.”

Carlson went on to help build a product called NeighborhoodAlerts.com for another local company, Three-Ships. NeighborhoodAlerts.com connects residents to the unfiltered news and information they need from police departments, public works departments and other verified news sources without the drama and spin common to other platforms.

Soon they extended the data sources on the platform to also tell users about new restaurants, trends in home values, severe weather and home improvement deals. The more value the platform can offer, the stickier it is to users and the greater variety of monetization opportunities emerge.

Key trends shaping the future of marketplaces

Seeing and contributing to the evolution of marketplaces through new technologies has been exciting, especially as it leads to more personalized and engaging experiences. To summarize the key trends we’re seeing in the future of marketplace solutions:

• Marketplaces are evolving into complex, AI-powered ecosystems that are hyper-personalized to users’ needs.
• AI is enhancing key elements, making them more personalized, efficient, and “sticky,” while powering features such as improved matching and helping users navigate complex workflows.
• Once the primary use case is established, marketplaces are layering in additional services and advanced matching to deliver ongoing value which leads to improved user engagement and unlocking new monetization opportunities.

Building the marketplaces of tomorrow

As marketplaces continue to evolve, the most successful ones will be those that leverage AI to create smarter, more personalized, and service-rich experiences. If you’re building the next generation of marketplace technology, thoughtbot can help you bring it to life.