Associate Director Real Estate

Chewy•Boston, MA

2d•$149,000 - $245,000•Remote

About The Position

At Chewy, we strive to become the most trusted and convenient online destination for pet parents and our partners, including veterinarians and service providers. Our success is measured by the happiness of the people and pets we serve, not simply by the products we deliver. That's why we continuously challenge ourselves to think outside the box and create exceptional experiences for our customers and partners. We are seeking an experienced Associate Director of Real Estate to lead our real estate transaction strategy across our Fulfillment Centers, Pharmacies, Customer Care sites, and Corporate Hubs. This leader will be responsible for developing and executing real estate strategies that support Chewy's rapid growth while balancing cost, speed, flexibility, and long-term operational needs. Reporting to the Director of Real Estate, Construction, and Procurement, this role will lead complex lease negotiations, dispositions, renewals, broker relationships, and portfolio optimization initiatives across a diverse real estate portfolio totaling millions of square feet. The successful candidate will partner closely with Operations, Supply Chain, Pharmacy, Finance, Legal, Workplace, Construction, and executive leadership to identify and execute solutions that enable Chewy's business strategy. This is a highly visible role requiring exceptional negotiation skills, financial acumen, executive communication, and the ability to influence decisions across multiple business functions.

Requirements

Bachelor's degree in Real Estate, Finance, Business, or related field.
10+ years of commercial real estate experience with significant transaction responsibility, including industrial, office, and healthcare or specialty-use facilities.
Demonstrated success leading transactions valued in the tens to hundreds of millions of dollars.
Extensive negotiation and relationship management skills.
Experience partnering with executive leadership and influencing complex business decisions.
Strong financial analysis skills with proficiency in Excel and real estate modeling.
Exceptional communication, executive presentation, and stakeholder management skills.
Ability to travel approximately 25–40%.

Nice To Haves

Master’s degree in Real Estate, Business Administration, Finance, or related field.
Professional certifications such as CCIM, SIOR, or CPM.
Familiarity with demographic analysis, labor market evaluation, and supply chain network optimization.
Comfort working in a pet-friendly environment

Responsibilities

Develop and execute real estate strategies supporting Chewy's Fulfillment, Pharmacy, Customer Care, and Corporate Hub portfolios.
Lead all aspects of complex real estate transactions including: new site acquisitions, lease renewals, dispositions, build-to-suit leases.
Own transaction negotiations from initial strategy through lease execution, partnering closely with internal Legal and external brokerage teams.
Build comprehensive financial analyses including NPV, occupancy cost modeling, incentive analysis, and scenario comparisons to support executive decision-making.
Lead market evaluations and site selection efforts by analyzing labor, transportation, incentives, operating costs, and real estate market conditions.
Develop executive-level recommendations balancing operational requirements, financial returns, risk, and long-term flexibility.
Manage national brokerage relationships and hold external partners accountable for market intelligence, negotiations, financial analysis, and execution.
Partner with Construction, Facilities, Workplace, Procurement, and Operations to ensure successful transition from transaction through occupancy.
Identify opportunities to reduce occupancy costs while maintaining operational flexibility.
Continuously improve transaction processes, reporting, governance, and portfolio analytics.
Mentor Real Estate Managers/Analysts as the team grows.
Travel domestically as needed.