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About Diploma Debt


Jeff Skinner

Jeff founded Diploma Debt back in 2015. After experiencing some success on Wall Street and in Real Estate, Jeff decided that he wanted to tackle a new challenge and start a business. In particular, a venture where he could help people.

Jeff saw the effects of student loan debt was having on young professionals, and that became the focus new venture. Jeff still holds a career in finance, and is a licensed principal.

Jeff was a two-sport athlete in college and had a brief professional career in Europe after his college playing days. Jeff and his family currently reside in northern NJ.

Ken O'Connor

Ken O’Connor has 20 years of experience in the higher education finance space, having served as a student advocate, financial aid advisor, and content creator in the non-profit and private sector and has deep knowledge about the student lending and repayment process.

Ken helps people make smart choices given the variety of options available to repay student loans – with emphasis on the personal needs of each individual circumstance.

When Ken is not helping people find student loan repayment solutions – you can find him hiking in Colorado enjoying the outdoors.

Diploma Debt provides student loan repayment help from a real person, helping you make wise choices about your options.

Managing student loan debt can get complicated. That’s why we help our clients through every step of the process to make it easy. We work together with you to ensure application clarity while reducing stress and saving time.

Ready to get started? At Diploma Debt we work around your busy schedule to help you – book your first consultation and let’s get your student loans handled without the headaches.

Ask us about our referral program designed to help more people with student loan consolidation solutions.


Personal Consolidation

We work with you directly through the application process, helping every step of the way – including the renewal of your application each year depending on program eligibility.

Business Services

Offer your company employees an added benefit of financial peace of mind. Provide student loan consolidation services to help best manage repayment headache free.


What We Do

Federal student loan debt management – we help our clients best handle their student loan debt with smart strategy and insight on a variety of repayment options.


Our Approach

At Diploma Debt we look at the client’s unique needs in consideration of their student loan repayment plan and help them with a solution that fits with their “big picture” goals. Some consolidation programs require annual renewal and we will be with you every step of the way.


Our Mission

To help our clients best manage and repay their student loans affordably.

Office Hours

Appointments booked on YOUR schedule