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Sr Director, Real Estate

Tailored Brands
Posted 3 hours ago
United StatesRemote$186.6K–$248.7KReal Estate & Property
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Tailored Brands, Inc. is a leading omni-channel specialty retailer of menswear, including suits and a broad selection of business casual offerings as well as the largest provider of tuxedo rental products in the U.S. and Canada. We operate retail stores in all 50 states and Canada. Our U.S. retail stores are operated under the brand names of Men’s Wearhouse, Jos. A. Bank, Men’s Wearhouse and Tux, and K&G Fashion. Our Canadian stores are operated under the brand name of Moores in ten provinces. Our purpose is to help our customers love how they look for moments that matter. We accomplish this by providing a personal, convenient, one-of-a-kind shopping experience with compelling products and world-class service. We help fulfill this mission by providing our employees with an engaging and inclusive workplace focused on teamwork, growth and respect. If you want to make a difference, be part of a great team and grow, you might be a perfect fit.

About the Job
We currently have an exciting opportunity for a Sr. Director, Real Estate to join our Real Estate team. Reporting to the SVP of Real Estate and Construction, this executive leader will have enterprise accountability for the strategy, governance and execution of Tailored Brands’ real estate program across all brands and markets. The Sr. Director will lead, coach and develop the Directors responsible for market strategy, site selection, lease negotiations, portfolio optimization and corporate real estate, ensuring consistent standards, disciplined execution and strong financial outcomes. This position will oversee the transactional management and strategic planning for retail stores, corporate offices, HUBs, Distribution Centers and other leased or owned properties. The role will provide senior leadership for relocation, replacement, renewal, expansion, closure, disposition and other real estate initiatives, serving as a key advisor to the SVP of Real Estate and Construction and executive partners across the Company.

What You’ll Do | Key Accountabilities
  • Leads and develops the Directors across the Real Estate organization by establishing clear accountability, priorities, performance expectations and operating rhythms; builds bench strength through coaching, mentoring, succession planning and effective talent management.
  • Establishes portfolio governance, decision criteria, approval processes and key performance indicators to ensure consistent, data-driven recommendations and execution across all real estate functions.
  • Partners with executive and cross-functional teams to identify opportunities, align real estate actions with corporate and brand strategies, and translate business priorities into actionable market and portfolio plans.
  • Oversees analysis of demographics, income levels, customer density, competitive activity, traffic patterns, retail synergies and other market data to determine site feasibility, portfolio opportunities and investment priorities.
  • Directs the development and performance management of the broker and developer network. Establishes company standards for site development and economic terms, ensures the Directors and brokers apply those standards consistently, and monitors results and service quality.
  • Provides senior oversight of lease and transaction negotiations, including rent and lease terms, site conditions, landlord contributions, business points and legal requirements. Serves as an escalation point for complex, high-value or strategically important negotiations in partnership with Real Estate and Legal leaders.
  • Maintains senior relationships with landlords, developers, brokers and strategic partners; represents Tailored Brands in important portfolio discussions and ensures the Company is positioned for future development opportunities.
  • Establishes disciplined pipeline, project management and reporting practices across the organization, ensuring timely escalation of risks, decisions, dependencies and resource needs.
  • Owns the accuracy and credibility of the new-store and real estate initiative pipeline, including 12- to 24-month opening projections, portfolio actions, lease events and other enterprise commitments.
  • Provides executive oversight of reporting for existing-location lease actions, new-store activity, owned assets, corporate properties and other real estate initiatives; uses reporting to drive accountability and continuous improvement.
  • Champions an owner’s mindset, balancing customer and brand needs with long-term portfolio value, risk management, capital discipline and total occupancy economics.
  • Oversees all transactions involving the owned-assets portfolio, including acquisitions, dispositions and sale-leaseback transactions, in coordination with Finance, Legal and other stakeholders.
  • Has strategic oversight of the portfolio of logistics and transportation HUBs, Distribution Centers, Corporate Offices and other corporate-supporting locations, including portfolio planning, lease strategy, capital needs and business continuity considerations.
  • Serves as a senior advisor to the SVP of Real Estate and Construction and executive leadership on enterprise real estate matters and leads other strategic initiatives as assigned.
Skills & Experience
  • Minimum Requirements: Bachelor’s degree required in Business, Real Estate or a related field; 15+ years of relevant experience, including significant experience leading real estate teams and complex, multi-market programs.
  • Preferred Requirements: Master’s degree in Business, Real Estate or a related field; 7+ years of people-leadership experience and a demonstrated track record overseeing retail real estate site selection, lease negotiations, portfolio strategy and high-volume transaction execution (20+ annual new deals at the team level).
  • Executive-level verbal and written communication skills; highly organized, detail-oriented and proficient in Microsoft Office and presentation tools.
  • Strong financial acumen, including the ability to interpret P&L statements, evaluate investment returns and occupancy economics, and guide the development of effective action plans tied to strategic objectives.
  • Knowledge of demographic mapping, market planning and real estate analytics tools required.
  • Exceptional people-leadership skills with the ability to attract, develop, coach and retain high-performing Directors and broader real estate teams.
  • Strong negotiation, influence and executive presence, with the ability to build alignment and make sound decisions at all levels of the organization and with external partners.
  • Deep understanding of complex leases, transaction structures, corresponding legal terms and real estate risk management.
  • Proficient in financial analysis, spreadsheets, presentations, portfolio reporting, pipeline management and enterprise program management.
  • Strategic thinker who can manage multiple priorities, make decisions with incomplete information, create operating discipline and drive accountability across a distributed organization.

Please note that you do not need to qualify for all requirements to be considered. We encourage you to apply if you can meet most of the requirements and are comfortable opening a dialog to be considered.
Work Environment, Physical & Mental Demands
  • Ability to sit and work at a computer keyboard for extended periods of time
  • Ability to stoop, kneel, bend at the waist, and reach daily
  • Able to lift and move up to 25 pounds occasionally
  • Must utilize visual acuity, speech and hearing, hand and eye coordination and manual dexterity necessary to operate a computer and office equipment
  • Hours regularly 40 hours per week, as work dictates, from remote location
  • Must be based on the East Coast or West Coast, near a major metropolitan airport.
  • A minimum of 25% travel is required, including market trips, industry conventions and other events, landlord and developer portfolio meetings, team meetings and other travel as designated by the SVP of Real Estate and Construction.
Benefits
This role is eligible for health, dental and vision insurance, prescription drug, retirement savings (401k, employer-funded retirement plans, deferred compensation, and other defined-benefit or defined-contribution), life insurance, accident and disability, paid time off for sick leave, vacation, bereavement, jury duty, holidays (9 days per year), wellbeing program, commuter, adoption assistance, legal services, and employee merchandise discounts.
Work-Life Balance
We understand the demands of work, school, family, and personal responsibilities. Through our work-life resources and programs we offer services for every stage of life to help you manage the day-to-day needs. We offer programs such as:
  • Meeting-Free Fridays (encouraged) | so you can catch up on work and self-development
  • Summer Fridays | from Memorial Day to Labor Day so you can enjoy a head-start to the weekend
  • Holiday Early Departure | close out early the business day before a company observed holiday
The starting salary for this position is $186,596-$248,747. Actual compensation within this range will be determined based on factors such as skills, experience, and qualifications. Other compensation may include a 25% Annual Incentive Plan (AIP) bonus paid out according to policy. Base pay information is based on market location and may be subject to prevailing wage laws, if applicable.

Note: To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed are representative of the knowledge, skill, and/or ability required and are not intended to be an exhaustive list of all duties, responsibilities or qualifications associated with this job.

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