Principal Recruiter - HIT Division

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Stephen Benson has been with Direct Recruiters since 2017 as a Healthcare Software Executive Recruiter. He works alongside Managing Partner and HIT Leader, Mike Silverstein, and a large team of HIT Recruiters and Researchers. As an Executive Recruiter, Stephen's focus is on Sales, Product Management, Customer Success, Engineering and Operations from the Director level through VP and the C-Suite.

Prior to working at Direct Recruiters, Stephen was a Professional Recruiter at two local Cleveland, Ohio recruiting firms. He has a proven track record of identifying the most highly qualified candidates and placing them with high growth, PE & VC backed healthcare software companies nationwide.

Stephen earned his Bachelor’s degree in Education, with minors in History and Political Science from Bowling Green State University and considers himself a lifelong learner.

Stephen is an avid Cleveland sports fan, enjoys reading, playing Lacrosse and golf, and spending time with his wife Alli, their son William and their German Shepard, Obi.

Contact Stephen Benson: 440-996-0580 /

Healthcare IT Recruiters | Healthcare Technology Executive Search | Open Roles 

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Stephen Benson Testimonials

B.T. – Candidate

“The entire process was a very good experience. Working with Steve was a joy! The entire staff at DRI are professional, great communicators and helpful with navigating the entire interview and selection process. I would highly recommend DRI.”

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K.M. – Candidate

“Steve was with me every step of the way. He provided thorough responses to my questions and checked in regularly to see how things were progressing. Overall experience was excellent. Steve was always available and ready to jump in to…

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M.A. – Candidate

“Steve was highly responsive and worked to get me into a role that matched my career goals after taking the time to understand what they were. Prep sessions prior to interviews made sure I knew who I was going to…

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R.W. – Candidate

“Can’t recommend Steve enough. He helped me find, apply, and secure a new role that fit exactly what I was looking for. Very responsive and always a phone call away through the whole process.”

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C.F. – Candidate

“Stephen was fantastic throughout the entirety of my recruitment and hiring process. He was very communicative and informative during each step. He came to every conversation with insights and helpful suggestions. Stephen made this a stress free transition. I hope…

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J.H. – Candidate

“Steve helped connect me to a great opportunity as an Engineering Leader for a growing healthcare startup. Beyond the initial connection, Steve was extremely helpful throughout the entire process. He communicated clearly and promptly. He provided excellent insights on the…

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Andy Sharma, Chief Revenue Officer, Sensely

“I have had the pleasure of working with Steve for the past six months. He is an exceptional HR professional with a deep understanding of the healthcare startup ecosystem. He was instrumental in finding the perfect match for me and…

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Sean Middleton, Chief Technology Officer, Navia Benefit Solutions, Inc.

“Stephen is a great recruiter. I had never gone through an outsourced executive recruiting process prior to my working with Stephen. He will guide you through every step of the process and help talk you through negotiations and provide guidance…

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Matthew Hanis, VP of Strategy, Medchat

“DRI has been a great partner in helping us expand our sales and marketing teams. They listen carefully, bring great candidates, and add value throughout the process. I highly recommend DRI as a search partner to rapidly fill roles with…

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G.C. – Candidate

“Steve was an amazing resource in finding my new position. From interview prep, to working through the offer process, to accepting the offer, to starting the new position, Steve was always proactively reaching out and making sure the process was…

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