DIRECTOR OF ACQUISITIONS

Job Description

Job Description

Role Overview
We are looking for a driven acquisitions professional who can source, structure, and close commercial real estate deals. This role is not focused on supporting transactions—it is responsible for creating and executing them.

If you have not personally sourced and closed deals, this is not the right role.

You will operate as the deal quarterback, owning opportunities from initial relationship and sourcing through closing. You will work closely with internal leadership but are expected to take initiative, move quickly, and push deals across the finish line.

Primary Responsibilities

Deal Sourcing & Origination
• Develop and maintain strong relationships with top brokers to gain early access to opportunities
• Proactively source off-market deals through direct outreach to owners, developers, and operators
• Build and manage a targeted pipeline through cold outreach and relationship development
• Consistently generate actionable deal flow aligned with company strategy

Deal Ownership & Execution
• Take full ownership of deals from initial underwriting through closing
• Drive LOI strategy, negotiations, and transaction momentum
• Coordinate internal and external parties including lenders, legal, brokers, and consultants
• Act as the central quarterback to ensure deals move efficiently and close

Underwriting & Investment Analysis
• Analyze opportunities and determine viability, risk, and return profile
• Build or oversee financial models as needed, leveraging internal support where appropriate
• Structure deals creatively to enhance returns and mitigate risk

Negotiation & Structuring
• Lead negotiations on LOIs, purchase agreements, and key business terms
• Identify and execute creative structures where appropriate (partnerships, seller financing, etc.)
• Maintain focus on getting deals done while protecting downside

Team Collaboration
• Work with internal leadership for strategic input and final approvals
• Utilize internal analytical support for underwriting and modeling
• Mentor junior team members by demonstrating how to source and close deals

Required Experience

• Bachelor’s degree in Real Estate, Finance, Business, or related field
• 7–12+ years of experience in real estate acquisitions, investments, or related field
• Strong financial modeling and underwriting skills
• Proven track record of successfully closing transactions
• Deep understanding of real estate markets and investment strategies
• Excellent negotiation, communication, and presentation skills
• Ability to manage multiple projects in a fast-paced environment
• Demonstrated experience sourcing and closing commercial real estate transactions
• Strong broker relationships and ability to generate proprietary opportunities
• Experience leading deals from initial contact through closing
• Comfortable operating independently and driving outcomes without heavy oversight

Preferred Background

• Experience with [specific asset class or market, if applicable]
• Existing broker and industry network
• Familiarity with ARGUS, Excel, and other real estate analysis tools
• Experience on the principal side, brokerage, or a small/mid-sized investment platform
• Exposure to a range of asset types and deal structures
• Familiarity with value-add and core-plus strategies
• Financial modeling capability (advanced modeling support is available internally)

Key Characteristics

• Deal-driven mindset with a strong bias toward execution
• Comfortable with direct outreach and relationship building
• Ability to operate with urgency and move deals forward
• Gritty, resourceful, and solutions-oriented
• Capable of balancing entrepreneurial drive with institutional discipline

Performance Expectations

• Source and close 3–5 deals annually
• Drive more than $20M in annual transaction volume
• Close 5–6 deals totaling $50M+ over a 24-month period
• Build a consistent, high-quality pipeline of opportunities
• Success is measured primarily by closed transactions

Compensation Structure

• Competitive base salary
• Performance-based bonuses tied to closed transactions
• Opportunity for deal-level participation and long-term promote

Work Environment

• Michigan-focused with potential expansion into the Midwest over time
• Entrepreneurial, fast-moving environment with institutional-level expectations
• High accountability with significant autonomy for proven performers

This role is designed for someone who wants to build a track record, take ownership of deals, and participate in the upside of the business.

Hillside Investments is a leading full service real estate investment firm with a diverse portfolio of properties and a strong commitment to strategic growth. We specialize in identifying and capitalizing on lucrative real estate opportunities across commercial and mixed-use sectors. We are looking for a detail-oriented, results-driven Professional to join our dynamic team and support our investment strategies.

Company Description

Hillside Investments is a leading full service real estate investment firm with a diverse portfolio of properties and a strong commitment to strategic growth. We specialize in identifying and capitalizing on lucrative real estate opportunities across commercial and mixed-use sectors. We are looking for a detail-oriented, results-driven Professional to join our dynamic team and support our investment strategies.