How AI Freelancers Help Thruhike Support Small Businesses

Based in Boston, Thruhike is a discovery platform that connects small businesses with local and visiting consumers interested in unique products and experiences. Founder Katherine van Hengel was inspired to start the company after seeing first-hand how difficult it could be for a local business to market effectively.

“I was always around local small businesses and communities growing up. My parents owned a small photo store and I worked at a cider mill,” van Hengel said. “I saw the struggles that business owners had to reach the audiences they wanted and fight against the larger, bigger brands.” 

In her market analysis, Van Hengel spoke with more than 3,000 vendors about the challenges they’re experiencing today. She found that many of the pain points were the same as what she remembered from growing up. 

“A lot of the businesses we spoke to didn’t have digital tech to help with outreach,” van Hengel said. “And I’ve always really loved the idea of taking things you are passionate about — whether it’s your favorite local spots or products — and connecting them to your community. With these two things in mind, I was inspired to create a marketplace that combined the help and support that small businesses needed on the tech side with local connections that allowed consumers to shop and share.” 

Today, Thruhike aggregates authentic insights from business owners, media publishers, chambers of commerce, and hospitality groups — turning all of this information into shoppable, personalized experiences that help small companies grow. 

The challenge

Van Hengel’s initial idea for Thruhike took off, rapidly developing from a concept into a working platform. But scaling the company presented a major challenge. The small founding team would need to build increased operational capacity, onboard vendors, create and digitize content, and conduct sales outreach … all without the budget for hiring a large full-time staff. 

Van Hengel decided to try engaging freelancers who could execute day-to-day tasks, analyze vendor data, and help automate repetitive processes, all while ensuring that Thruhike’s high standards for personalization and community connection remained intact.

But van Hengel knew that she also needed freelancers who could hit the ground running and execute projects effectively with minimal oversight.

The solution: Upwork

Van Hengel turned to Upwork, where she found the capacity to scale without committing to full-time hires. Upwork’s flexibility enabled Thruhike to onboard freelancers for short-term needs, assess fit, and continue the engagement or shift as necessary — with minimal risk or friction. This dynamic approach allowed Thruhike to grow sustainably and adapt quickly to changing priorities.

“It’s been nice having the flexibility to ingrain people without the burden of having them as full-time employees,” van Hengel said. “We’re using the logistical piece of Upwork, but they’re very much coming into our systems. The platform has allowed us to come into a space with tons of experts, find the exact fit we need, and move really quickly in terms of testing and finding product market fit. We can move rapidly from idea to idea.”

And with the help of freelancers on Upwork, those ideas have turned into real processes for optimizing internal workflows, speeding up content curation, and more. Many of these processes are augmented with AI in a way that balances the efficiencies AI brings and the connections between people that are at the core of Thruhike’s being.

“I think every list and product and story that someone engages with on our platform now has a little bit of AI in it, due to our processes and the Upwork talent who’ve helped us get there. But overall, if we take a step back, Thruhike is still very human because of this balance we’ve created,” van Hengel said. “It’s really rooted in real life, and real people. We’re specialists connecting consumers to things they love, and you can’t do that through technology alone.” 

The results

Since engaging freelancers on Upwork, van Hengel and the Thruhike team have seen a variety of benefits — all of which allow them to serve more much-loved local businesses around the world.   

Streamlined operations 

By leveraging AI for internal workflows and automating routine tasks, Thruhike significantly reduced its operational load. Processes like email management, data collection, and backend tasks were enhanced by AI tools, freeing the core team to focus on strategic growth and product development.

“Our project time has been reduced from a month to a week,” van Hengel said. “And we fluctuate from one to four to 10 freelancers depending on need. You really can’t beat that.”

Increased budget flexibility

Strategic use of AI — and freelance talent — has also allowed Thruhike to scale their operations and revenue without scaling full-time headcount. 

“We’ve saved the equivalent of two full-time salaries in a year of using Upwork — upward of $200,000 saved for the year,” van Hengel said. “This is huge for us at our stage.” 

Building locally by scaling intelligently

Thruhike’s success demonstrates how a modern startup can scale intelligently by combining flexible talent, selective automation, and mission-driven design. And behind it all, there’s an all-important team of dedicated people — from the company founder to specialized freelancers. 

“Having the ability to find talent and specialists out in the world who can dig into our projects is so helpful,” van Hengel said. “And Upwork has been there at every step of the way, able to pivot with us.”