Now Hiring Underwriting Analyst - Paid Internship

Founded in 2018, Cutter Hill Capital is a private real estate lender focusing on loans for short-term real estate investment projects in the greater New England region and select national markets.

Cutter Hill Capital prides itself on being able to provide financing to a wide variety of real estate investors by creatively structuring loans to meet the needs of the borrower.  As a direct lender with discretionary capital, we have the flexibility to accommodate most scenarios with the intent of ensuring the success of the borrower. We exercise discipline in our business practices and remain resolute in our commitment to innovate and grow as a leader in our industry and community.

Join the team!

Work With Cutter Hill Capital


  • -Conduct preliminary analysis for all new loan submissions

-Review the viability of the loan with the manager

  • -Conduct a site inspection for new loans
  • -Complete a comprehensive investment summary report for all viable loans that will be pursued
  • -Complete a review of the submitted documents for all construction draw requests and conduct a site inspection to verify the progress on the project
  • -Assist with social media and marketing efforts


  • -Must be located in the greater Boston area
  • -Strong desire to learn about the world of commercial real estate
  • -Business or finance background
  • -Access to personal transportation
  • -Flexible schedule and availability of 10-20 hours per week
  • -Ability to meet short-term deadlines
  • -Proficient with Microsoft Excel
  • -Familiar with primary social media platforms


  • -Hourly compensation – $25/hr
  • -Commission opportunity for directly originating new loans
  • -Commission opportunity for securing new investors


We invite candidates to apply who have the ability to begin immediately as well as those candidates who will be able to begin by June 1st. 

Cutter Hill Capital is a new and growing business.  We hope the successful candidate will be able to grow into a full-time role with the company with expanded responsibilities.  We value hard work, an inquisitive mind, and an eagerness to learn.

How To Apply

- Email your resume and cover letter to

Work with Cutter Hill Capital