Director Real Estate

Ayr Wellness • Miami, FL

2d • Remote

About The Position

The Director of Real Estate leads Ayr’s real estate strategy and execution across our multi-state footprint, from market evaluation and site selection through lease negotiation, build-out handoff, and ongoing lease portfolio management. This role sits at the intersection of real estate, cannabis regulation, and operations: identifying locations that meet both commercial criteria and state and local cannabis requirements, building the business case for each site, and guiding deals from LOI to signed lease in close partnership with Legal, Compliance, Finance, Construction, Facilities, and Retail Leadership. This role also owns the ongoing management of Ayr’s lease portfolio and landlord relationships and manages the performance of our external brokerage partners. This is a high-visibility, high-travel role supporting an active expansion pipeline. Success in this role is measured by pipeline coverage against planned openings and licensing deadlines, entitlement approvals, on-time and on-budget store openings, occupancy cost as a percentage of sales, and new-store payback.

Requirements

• Deep knowledge of commercial real estate, including site selection, market analysis, lease structures, and lease economics.
• Proven ability to negotiate LOIs and leases and to partner effectively with legal counsel on lease terms.
• Working knowledge of zoning, land use, and permitting processes; ability to navigate state and local regulatory requirements in a highly regulated industry.
• Strong financial acumen, with the ability to build and interpret site-level financial models (e.g., MPV, occupancy cost, sales-to-rent).
• Experience managing brokers and external vendors and holding them accountable to scope, timelines, and results.
• Familiarity with construction and facilities processes, including physical diligence and build-out coordination.
• Excellent executive communication skills, with the ability to present recommendations and analysis to senior leadership.
• Highly organized, with the ability to manage multiple concurrent deals and a large lease portfolio across markets.
• Proficiency with lease administration systems (e.g., Lease Query), mapping/GIS tools, and Microsoft Office.
• Familiarity with cannabis license application and scoring processes, with the ability to align site strategy to licensing timelines.
• Strong negotiation and deal-structuring skills, with comfort operating amid a fast-changing legal and regulatory landscape.
• 8+ years of progressive commercial real estate experience in retail, site selection, lease negotiation, and/or portfolio management, including multi-site or multi-state expansion.
• Experience in a regulated retail category (e.g., cannabis, pharmacy, liquor, gaming, or convenience) strongly preferred; cannabis industry experience is a plus.
• Demonstrated track record of taking sites from market evaluation through executed lease and opening.
• Prior leadership experience (3+ years preferred), including building and leading a team.
• Must be 21 years of age or older and able to obtain and maintain any required state or local cannabis agent badge or license, including background checks.
• Must hold a valid driver’s license and be able to travel by car and air.

Nice To Haves

• MBA, JD, or CCIM/SIOR designation a plus.
• Experience managing or auditing external brokerage relationships preferred.
• Existing relationships with cannabis-friendly landlords, brokers, and municipal contacts a plus.

Responsibilities

• Lead market evaluation for new locations using defined site criteria, including population density, demographics, employment and growth trends, universities, and regional drivers.
• Build and maintain a multi-state site pipeline aligned to licensing application windows, capital plans, and opening targets, with enough pipeline coverage to absorb site attrition.
• Conduct white-space mapping and competitive reviews to prioritize target cities and regions; partner with IT on mapping and sensitive-use (buffer zone) analysis.
• Direct and oversee brokerage partners in identifying available properties that meet site criteria including requirements such as traffic, visibility, size, parking, and access.
• Partner with Facilities to evaluate power, water, utilities, and logistics, including proximity to the retail locations being supplied.
• Validate that target jurisdictions permit cannabis operations (zoning, municipal moratoriums, special use requirements) and that sites align with state licensing requirements, including buffer zones and distance restrictions from sensitive uses and other dispensaries, in partnership with Compliance and Legal.
• Coordinate with Licensing and Compliance so site decisions line up with application windows and scoring criteria.
• Support community and local government engagement, such as town halls and special use permit processes, as required by the jurisdiction.
• Partner with Finance to build site-level financial analysis (MPV) and KPIs for each opportunity.
• Develop market-entry analyses using demographics, traffic, competitor density, and sales forecasts to support new-market and in-market growth decisions.
• Prepare and present site recommendations to executive leadership for review and approval and coordinate final sign-off through the approval chain.
• Coordinate internal alignment on high-level deal terms before LOI, including asking rent, offer strategy, landlord risk tolerance, environmental diligence, and site requirements.
• Lead the negotiation of business terms for LOIs and leases, including economics, term, renewal options, escalations, and tenant improvements.
• Negotiate cannabis-specific lease terms, including license contingencies, extended due diligence periods, and landlord compliance provisions; structure leases, purchases, and sale-leasebacks as appropriate.
• Work closely with Legal on lease drafting, clauses, and contract risk through execution.
• Structure deals that account for federal-law risk, banking limitations, and tax considerations such as IRC 280E, in partnership with Legal and Finance.
• Provide required real estate documentation to support state and local licensing applications, coordinated with Compliance and Asset Protection.
• Build and maintain relationships with cannabis-friendly landlords, developers, brokers, and REITs to expand access to viable sites.
• Engage Construction at the LOI stage to initiate physical diligence (e.g., HVAC, structural, and building systems) and confirm the site is fit for purpose.
• Serve as the real estate point of contact for Construction, Facilities, architects, and designers through build-out, and support the handoff to Retail Leadership and Facilities for store design and opening.
• Partner with Construction, Design, and Asset Protection to deliver stores on budget and on schedule, tracking build-out cost against budget and time from lease execution to opening.
• Own Ayr’s lease portfolio across all markets, including the lease administration system (Lease Query), critical dates, renewals, rent escalations, and compliance with lease terms.
• Serve as the primary contact for landlords, managing ongoing inquiries, disputes, and ancillary charges such as common area maintenance (CAM) reconciliations.
• Partner with Finance, Legal, Compliance, and Retail on renewal, relocation, expansion, and exit decisions.
• Maintain accurate portfolio reporting and recommend opportunities to reduce occupancy costs.
• Conduct rent audits and CAM and tax reconciliation reviews to identify savings and recover overcharges.
• Monitor store-level performance (sales per square foot, four-wall EBITDA, occupancy cost as a percentage of sales, and payback) and recommend optimization, relocation, or exit for underperforming locations, with a defined action plan for each.
• Report pipeline status, capital spend, and portfolio performance to executive leadership and the board.
• Manage and audit external brokerage relationships, including broker selection, scope, performance, and fees.
• Establish consistent real estate processes, templates, and governance to support a repeatable, scalable expansion model.
• Manage external partners, land-use counsel, and consultants, holding them accountable to scope, cost, and timelines.
• Hire, develop, and lead real estate team members (such as managers, analysts, and coordinators) as the pipeline and portfolio grow.

Benefits

• We are committed to building a team that represents a variety of backgrounds, perspectives, and skills. We do not discriminate on the basis of race, color, religion, creed, national origin, ancestry, sex (including pregnancy, childbirth, or related medical conditions), sexual orientation, gender identity or expression, age, disability, genetic information, marital status, military or veteran status, or any other protected status in accordance with applicable federal, state, and local laws.

What This Job Offers

• Job Type: Full-time
• Career Level: Director