Vice President, Real Estate

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

Benefits offered by this job

Direct exposure to principals

Growth opportunities

Entrepreneurial culture

Competitive compensation

Job summary

Highland Holdings is seeking a leader to drive real estate expansion, acquisitions, and development across our portfolio of retail, gas stations, QSRs, and mixed-use projects.

You will shape the future of our real-estate division by leading deal sourcing, underwriting, and capital strategies, while collaborating with the executive team to accelerate growth and optimize asset value.

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 business goals.
• Visionary mindset—you aim to think big.

Responsibilities

• Lead our real-estate expansion, acquisitions, and development strategy.
• Identify, acquire, and develop properties that fuel our brands’ growth, while driving strategic real-estate investments.
• Work directly with the executive team to shape the future of our real-estate division.
• Oversee projects from ground-up construction to tenant placement.
• Plan acquisition and roll-out of our brands to new states/markets and secure long-term advantages.
• Build financial models to determine the best opportunities and underwrite deals.
• Help shape investment strategies, including SPVs, real-estate funds, and joint ventures.
• Decide which properties to hold, sell, or reposition for maximum value.

Skills

Real estate development

Acquisitions

Asset management

Franchise expansion

Financial modeling

Negotiation

Capital raising

Underwriting

Tools

Excel

Job description

Overview

We don’t just invest in real estate—you 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 are 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.

Job Type

Full‑time.

Responsibilities

• Lead our real‑estate expansion, acquisitions, and development strategy.
• Identify, acquire, and develop properties that fuel our brands’ growth, while driving strategic real‑estate investments.
• Work directly with the executive team to shape the future of our real‑estate division.
• Oversee projects from ground‑up construction to tenant placement.
• Plan acquisition and roll‑out of our brands to new states/markets and secure long‑term advantages.
• Build financial models to determine the best opportunities and underwrite deals.
• Help shape investment strategies, including SPVs, real‑estate funds, and joint ventures.
• Decide which properties to hold, sell, or reposition for maximum value.

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 business goals.
• Visionary mindset—you aim to think big.

What We Offer

• Direct exposure to principals and real‑time decision‑making.
• Growth potential within a high‑velocity platform scaling across new asset types.
• Entrepreneurial culture where ideas are heard and performance is rewarded.
• Meaningful compensation tied to impact.

Compensation

$175,000-200,000 Base + Variable Compensation Package.