Summary
Overview
Work History
Skills
Languages
Timeline
Generic

Chaim Schechter

Spring Valley

Summary

Real estate professional with experience across commercial acquisitions, distressed asset repositioning, investment analysis, and investor advisory. Brings a steady, solutions-oriented approach to complex situations, with a reputation for integrity, clarity, and sound judgment. Known for helping investors stabilize underperforming assets through thoughtful analysis, operational restructuring, and clear communication. Collaborative, motivated, and execution-focused, with a positive and professional working style.

Overview

5
5
years of professional experience

Work History

Real Estate Advisor

HeadSight | Headsightre.com
Spring Valley, NY
01.2023 - Current
  • Provide objective real estate guidance to investors seeking clarity on existing or prospective investments
  • Assist clients with underperforming assets by analyzing financials, operations, and deal structure
  • Help investors stabilize assets, restructure operations, or determine appropriate exit strategies
  • Operate as a part-time service-driven initiative focused on education, transparency, and investor protection
  • No commissions or financial incentives tied to transactions

Off-Market Brokerage

Self-employeed
Spring Valley, NY
01.2023 - Current
  • Brokered off-market, multi-million-dollar real estate transactions by connecting buyers and sellers and remaining actively involved through diligence, coordination, and closing
  • Supported transactions end-to-end by maintaining alignment between parties, addressing issues, and ensuring forward momentum
  • Operated in a non-broker capacity; relied upon for discretion, follow-through, and trust

Private Portfolio

Self-employeed
Spring Valley, NY
08.2021 - Current
  • Acquired severely distressed residential properties and led full repositioning from acquisition through profit
  • Oversaw renovation strategy, capital planning, and value-add execution
  • Work closely with third-party property management while retaining oversight of all major decisions
  • Successfully stabilized assets and achieved profitable exits through disciplined execution

Aquisitions

ME Real Estate
Columbus, OH
08.2020 - 08.2021
  • Supported commercial real estate acquisitions for an international investment group
  • Conducted financial and operational due diligence, including review of operating statements, rent rolls, and deal assumptions
  • Assisted in evaluating risk, structure, and value-creation opportunities
  • Collaborated closely with senior team members throughout the acquisition process

Skills

  • Commercial Acquisitions & Due Diligence
  • Off-Market Transaction Execution
  • Distressed Asset Repositioning
  • Investment & Operational Analysis
  • Deal Structuring & Risk Review
  • Investor Guidance & Support
  • Stakeholder Coordination
  • Clear, Professional Communication

Languages

English
Full Professional
Hebrew
Native or Bilingual

Timeline

Real Estate Advisor

HeadSight | Headsightre.com
01.2023 - Current

Off-Market Brokerage

Self-employeed
01.2023 - Current

Private Portfolio

Self-employeed
08.2021 - Current

Aquisitions

ME Real Estate
08.2020 - 08.2021
Chaim Schechter