How Ruben Hassid Leverages AI and Upwork for Hiring Top Freelancers

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Ruben Hassid

LinkedIn Author

Master AI before it masters you.

In a recent LinkedIn post, Ruben Hassid discusses a novel approach to talent acquisition, detailing how he utilizes artificial intelligence, specifically Claude, in conjunction with the Upwork platform to identify and recruit freelance professionals. Hassid emphasizes that while AI is a powerful tool, it’s the combination of AI-powered tools and skilled human talent that yields the best results.

Hassid outlines a four-step process for leveraging AI in the hiring workflow. He begins by directing readers to their ‘Connectors’ within Claude, suggesting that if the Upwork connector isn’t immediately visible, it can be found under the ‘+’ option or by browsing available connectors. For those who still can’t locate it, Hassid provides a direct link to Upwork’s AI plugin page.

Streamlining the Recruitment Process with AI

The core of Hassid’s strategy lies in effectively prompting the AI. He advocates for using voice input to expedite the process, advising users to clearly describe the desired role and the ideal candidate profile. A key recommendation from Hassid is to specifically ask the AI for a diverse mix of potential candidates.

“Describe what you want + who you’re looking for. I like to ask for a different mix of people.”

Following the prompting stage, Hassid moves to the ‘Post & DM’ phase. He explains that Claude can be used not only to generate a public job listing but also to draft direct messages for top-tier talent identified through the AI’s search. This dual functionality, according to Hassid, significantly streamlines the outreach process.

The Role of Upwork in Modern Hiring

Hassid reiterates his confidence in Upwork as a premier platform for finding skilled freelancers. He notes the platform’s substantial economic impact, mentioning that Upwork has facilitated over $30 billion in earnings for its users. This underscores his belief in the platform’s reliability and effectiveness in connecting businesses with quality talent.

“Sounds obvious, but this is still the # 1 platform to find solid freelance talent. AI is awesome, but talented people using AI are even better!”

He further elaborates on the practical application, sharing a direct prompt example: “Use Upwork MCP and find [job description].” This prompt, Hassid suggests, can be used with any preferred AI, including ChatGPT.

Integrating AI with Human Expertise

A central theme in Hassid’s post is the synergy between AI and human capability. He argues that while AI tools are transformative, their true potential is unlocked when utilized by skilled individuals. This perspective positions AI not as a replacement for human recruiters or hiring managers, but as a powerful assistant that augments their abilities.

“I am hiring, using Claude & an MCP.”

Hassid’s insights offer a practical guide for businesses looking to modernize their recruitment strategies. By combining the efficiency of AI with the proven effectiveness of platforms like Upwork, companies can potentially discover and engage with a broader and more qualified pool of freelance talent. His approach highlights a forward-thinking strategy that embraces technological advancements while remaining grounded in the importance of human skill and judgment.

📝 About This Content

This article is based on insights shared by Ruben Hassid on LinkedIn.

📅 Originally posted on October 1, 2026 | View original post on LinkedIn →