Senior Real Estate Investment Associate - Multifamily (Remote/Travel)

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About the Opportunity

Aspen Square Management, one of the nation’s largest privately held real estate investment and property management firms with over $2 Billion in assets, is seeking a hard-working, entrepreneurial Senior Investment Associate. This an opportunity to be part of a team charged with doubling our portfolio size through new acquisitions by the year 2030. If you’re a motivated self-starter with a passion for real estate investment, then this is the opportunity for you! Mentorship from a talented team, exceptional opportunities for growth, a generous compensation package and one-year partnership/equity track make this opportunity very attractive for the right candidate.

The Investment Associate position offers a blend of real estate sourcing through direct outreach to potential sellers, real estate finance, investment strategy, as well as business analysis. The role allows you to work hands-on with an experienced team of real estate investors and operators, as part of a collaborative and thriving Real Estate Acquisitions Department.

About the Company

Aspen Square Management is based in Massachusetts. Founded by entrepreneur, philanthropist and real estate guru Harold Grinspoon, Aspen combines the energy and creativity of a startup, the benefits of a 60-plus year track record of success, the scale and financial resources of a large organization, and the close-knit feel of a family business.

Known for its fast-paced, entrepreneurial, people-centric culture, Aspen Square invests primarily in value-add multifamily real estate investment opportunities. (In other words, we buy apartment communities, renovate, rebrand, and reposition them, and then either hold properties for the long-term or sell them under the right circumstances.) We are investors AND owner/operators. Our current portfolio consists of 14,000 apartments located in 15 states throughout the country valued at over $2 billion. We employ about 600 employees, with approximately 100 of those employees working in the Greater Springfield area. “Aspenites” often join us early in their careers here and grow with us for decades.

About the Role

The Senior Investment Associate is an active member of the team charged with identifying, sourcing, underwriting, and executing any and all potential multi-family housing investments, anywhere across the country. Responsibilities include:

  • Research local real estate markets and thematic trends to identify areas of opportunity
  • Source acquisition opportunities by building and maintaining relationships across markets, “Bird dogging” potential sellers, and calling on intermediaries to generate property leads
  • Evaluate potential acquisitions
  • Conduct thorough due diligence on target properties, including traveling to sites and markets to conduct on-the-ground underwriting and analysis
  • Communicate and present investment opportunities to the Acquisitions team and company leadership
  • Work collaboratively across the company to inform underwriting and investment recommendations


  • A gritty, driven, determined and persistent self-starter with a passion for real estate who is motivated to work their way up
  • An entrepreneurial spirit and growth mind-set
  • 5 – 7 Years experience in business - real estate investment and/or brokerage experience preferred
  • Bachelor’s Degree required. Degree in Business, Real Estate, Finance, or a related field of study preferred
  • Exceptional communication skills and strong interpersonal skills
  • Willingness to travel nationally
  • Ability to work independently and as part of a team
  • Desire for professional growth and advancement

Compensation & Benefits Package:

  • Lucrative one-year partnership/equity track
  • Generous salary commensurate with experience
  • Comprehensive benefits program to include health, dental and vision insurance
  • 401K Retirement program & match
  • Long-term disability insurance
  • Opportunity to travel nationally (paid for by the company)
  • Great work-life balance
  • Opportunity to work in a field you’re passionate about in a fun, fast-paced environment with a talented, dynamic team and successful
  • Mentorship by a department head willing to develop you professionally