Vice President, Real Estate

Luckylincolngaming; Chicago (IL); On-site; USD 175,000 - 200,000; Full time

Job summary

Luckylincolngaming seeks an executive-level real estate leader to drive expansion, acquisitions, and development strategy across retail, QSR, hospitality, and large-scale mixed-use assets.

You will build financial models, lead capital raising, structure deals, and guide portfolio growth with an entrepreneurial mindset to scale quickly.

Qualifications

• 7+ years in real estate development, acquisitions, asset management, or franchise expansion.
• Experience in retail, QSR, hospitality, or mixed-use real estate.
• Strong deal negotiation and capital-raising experience.
• Ability to underwrite and prioritize acquisitions based on strategic goals.

Responsibilities

• Identify prime locations for QSRs, gas stations, strip centers, and large-scale developments.
• Oversee development projects from ground-up construction to tenant placement.
• Plan market expansion and rollout of brands to new states/markets.
• Build financial models to evaluate opportunities and drive investment decisions.
• Structure deals and capital plans including SPVs, real estate funds, and joint ventures.
• Decide which properties to hold, sell, or reposition for max value.

Skills

Deal negotiation

Capital raising

Underwriting

Acquisitions

Development strategy

Market expansion

Job description

We don’t just invest in real estate—we own, develop, and operate businesses that make those properties thrive. Our portfolio spans retail strip centers, gas stations, QSRs, and large-scale mixed-use developments.

We’re not your typical real estate investment firm. We’re strategic operators, acquiring locations to expand our brands—Lindy’s gas stations and Aviator Coffee —while also building a diverse commercial real estate portfolio. Whether it's acquiring a retail strip center, redeveloping a multi-acre parcel, or launching a new hospitality brand, we move fast and think big.

Requirements

We’re looking for a high-level real estate executive to lead our real estate expansion, acquisitions, and development strategy. This person will be responsible for identifying, acquiring, and developing properties that fuel our brands’ growth, while also driving strategic real estate investments.

You’ll work directly with the executive team to shape the future of our real estate division, leading efforts in:

• Site Selection & Acquisitions: Identify prime locations for QSRs, gas stations, strip centers, and large-scale developments.
• Development Strategy: Oversee projects from ground-up construction to tenant placement.
• Market Expansion Strategy: Plan how to acquire key real estate and roll out our brands to new states/markets and secure long-term advantages.
• Underwriting & Investment Analysis: Build financial models to determine the best opportunities.
• Capital Raising & Deal Structuring: Help shape investment strategies, including SPVs, real estate funds, and joint ventures.
• Divestitures & Asset Management: Decide which properties to hold, sell, or reposition for max value.

This role requires an entrepreneurial mindset, a deep understanding of real estate investment and development, and the ability to scale a fast-moving portfolio.

What We’re Looking For

• 7+ years in real estate development, acquisitions, asset management, or franchise expansion.
• Experience in retail, QSR, hospitality, or mixed-use real estate.
• Strong deal negotiation and capital raising experience.
• Ability to underwrite and prioritize acquisitions based on strategic business goals.
• A visionary mindset—we’re thinking big, and you should be too.

This is an executive-level position with the opportunity to lead a major real estate operation from the ground up.

Why Join Us?

• Direct exposure to principals and decision-making that actually happens in real-time.
• Growth potential inside a high-velocity platform scaling across new asset types.
• Entrepreneurial culture where ideas get heard, and performance gets rewarded.
• Meaningful compensation tied to your impact.

Salary Description

$175,000-200,000 Base + Variable Comp Package