Managing Director

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Position Title: Senior Vice President / Managing Director – CRE & Special Situations

Location: Los Angeles or Boston

Reports to: CEO

Seniority Level: VP, SVP, or MD (10–20+ years of experience)

Company Overview:

Cottonwood Group is a private equity real estate investment firm with offices in Los Angeles, Boston, and New York. The firm specializes in equity and debt investments across diverse property sectors and geographies, leveraging its flexibility to act as a lender, investor, operator, and sponsor. Cottonwood targets U.S. real estate investments with a capitalization of up to $1 billion, offering creative financing solutions and delivering risk-adjusted returns to investors.

Position Overview:

We are seeking a seasoned and versatile real estate investment professional to join our team, with the capability to contribute across investments, capital markets transactions, and special situation/workout efforts. This role is ideal for a candidate with a deep understanding of commercial real estate (CRE) and the agility to support strategic investments while also engaging in complex loan restructurings, foreclosures, and asset repositioning.

This role is a unique opportunity to partner directly with senior leadership to analyze, underwrite, and execute on real estate transactions across the capital stack, while also serving as a key resource within our special situations group to evaluate distressed assets and develop workout strategies.

Key Responsibilities:

• Support the special situations group in loan workouts, restructurings, foreclosures, and REO management.
• Executes capital market transactions, including but not limited to debt syndication, back-leverage, and/or sell-down.
• Analyze distressed debt portfolio and develop recovery strategies.
• Engage with legal, property management, and external consultants as needed during workouts.
• Contribute to valuations, risk analysis, and resolution planning.
• Source, evaluate, and underwrite real estate debt, equity and development opportunities across various asset types and geographies.
• Develop investment memos, financial models, and sensitivity analyses and present to the Investment Committee.
• Oversee due diligence, deal structuring, and closing processes.
• Collaborate with portfolio management and finance teams to optimize portfolio performance.

Qualifications:

• Bachelor’s Degree in Business Administration, Real Estate, Economics, Finance, or related focus of study preferred or a minimum of 10 years.
• 10–20+ years of relevant experience in commercial real estate, ideally across investments, structured finance, and/or development.
• Broad experience with CRE debt (including full-stack), equity, and development assets.
• Strong underwriting and financial modeling expertise (Excel proficiency required).
• Experience in workouts, restructures, and special situations highly preferred.
• High level of judgment, risk assessment, and strategic thinking.
• Exceptional interpersonal, negotiation, communication and business writing skills.
• Ability to travel as needed for diligence of investment opportunities and asset management of existing investments.
• Ability to interpret and navigate through complex legal documents and negotiate them towards defined business goals.

More about you:

You are passionate about real estate and looking to join a hyper growth-focused firm. You have experience with broad capital markets knowledge, deep transaction experience, and the ability to toggle between new investments and complex asset resolution. You understand debt, equity, and development positions. You are analytical, solutions-driven, and comfortable with ambiguity in dynamic deal environments. Strong interpersonal skills and the ability to navigate internal and external stakeholders are highly valued.

Why join our team?

• Be part of a firm that has consistently grown throughout market cycles, institutional investment grade while maintaining its nimble and entrepreneurial culture.
• Collaborative, respectful, supportive, and entrepreneurial culture.
• Beautiful office in Downtown Los Angeles/Boston, both with access to great restaurants and food trucks.
• Hybrid schedule that supports a healthy work-life balance with generous time off.
• Passion to provide opportunity for growth.
• Attractive and competitive compensation package.
• Rich benefit plans including affordable medical, dental, and vision coverage and 401K with up to 4% match.
• Company paid Long Term Disability and Life Insurance.

Compensation: Base plus bonus structure – wide range based on knowledge and experience.

Cottonwood is an equal opportunity employer which takes pride in diversification and providing an environment where all team members can thrive. We do not unlawfully discriminate on the basis of any status or condition protected by applicable federal or state law.

Seniority level

• Seniority level

  Director

Employment type

• Employment type

  Full-time

Job function

• Job function

  Analyst, Finance, and Other

• Industries

  Financial Services and Investment Management

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Inferred from the description for this job

Medical insurance

Vision insurance

401(k)

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