Regional Director of Sales and Operations
Middleburg Communities, Tampa, FL, United States
Brief Description
The Regional Director, Sales and Operations is a highly mobile, performance-focused role designed to provide hands‑on operational and leasing leadership to site teams, performance optimization across a small group of assets (typically 2–3 communities), and assist with research and support of pipeline projects. The position partners closely with Operations Leadership, Asset Management, Development, and onsite teams to drive performance, stabilize operations, and execute strategic initiatives across the asset lifecycle. This role is intended for a motivated, high‑expectation operator with strong analytical skills, revenue and demand‑generation acumen, and an understanding of real estate finance principles and the development process. The Director must be able to proactively and quickly and accurately diagnose and overcome complex operational challenges, prioritize leasing velocity, and protect revenue while driving disciplined execution. The Regional Director, Sales and Operations is not solely an operational supervisor. They are the primary sales leader for their portfolio and are expected to drive performance standard, enforce accountability, and inspire and foster growth. The role will also be heavily involved in pre‑operations and development support, providing analysis and recommendations from due diligence through construction and stabilization.
This position can be based out of Tampa FL, Orlando FL, Raleigh NC, Charlotte NC, or Richmond VA.
Essential Duties And Responsibilities Portfolio Performance
Serve as leader for assigned communities, providing support and empowerment on leasing, sales, and marketing strategy, expense management, unit acceptance, staffing structure, and service delivery
Quickly and proactively diagnose and anticipate performance gaps (conversion, closing, lead generation, occupancy dips, NOI, customer experience, compliance) and develop clear, actionable improvement plans to which onsite teams are held accountable
Translate asset management strategy into executable onsite tactics
Operational Execution
Lead targeted interventions at underperforming or transitioning assets (lease‑ups, staffing resets, ownership transitions)
Support implementation and compliance of SOPs, systems, and new initiatives, ensuring consistency and adoption at the site level
Partner with onsite leadership to elevate operational rigor, accountability, decision‑making, and sales performance
Pre‑Operations Services
Assist Operations leadership in advising on rents, budgets, unit mix, design, and marketing for proposed developments
Cross‑Functional Partnership
Act as a bridge between Operations, Asset Management, Marketing, and partners/ownership
Support ownership/partner and leadership communication and site‑level readiness for investor interactions as needed
Travel & Field Presence
Maintain a high field presence, traveling frequently to assigned communities and/or development sites and submarkets
Be hands‑on and visible onsite and in markets—this role is not desk‑based
Requirements Knowledge and Experience
Undergraduate degree with a concentration in real estate, finance, strategy, operations, marketing, or entrepreneurship (MBA preferred)
4–7 years of experience with progressive leadership responsibility in real estate, hospitality, franchise operations, consulting, investment management, operations; exposure to asset‑level decision‑making strongly preferred
Experience managing teams—developing top performers and counseling under‑performers, ability to quickly identify and address personnel issues
Strong financial and analytical foundation, including comfort with underwriting assumptions, pro‑formas, operating budgets, revenue drivers, and translating financial insights into actionable operations
Demonstrated ability to effect positive performance results, moving seamlessly between data analysis, field execution, team management and motivation, and stakeholder management
Comfort with ambiguity and imperfect information; able to form hypotheses, test solutions in real time, and make sound recommendations without extensive oversight
Executive presence and communication maturity beyond years of experience; capable of interacting directly with ownership, asset management partners, and senior leadership, and onsite teams with confidence and credibility
Hands‑on orientation—intellectually curious but not desk‑bound; eager to be onsite, understand frontline operations, and see strategies executed in the real world
High standards and resilience; able to absorb feedback, handle pushback, and operate in a KPI and performance‑driven environment
Strong judgment, discernment, and integrity, particularly in owner‑facing or sensitive portfolio situations
Highly organized self‑starter with the ability to manage multiple priorities across a small portfolio of geographically dispersed assets
Willing and able to travel extensively and on short notice, with enthusiasm for field work and exposure to multiple markets and diverse asset types
What we can offer you
Great benefits—comprehensive health and wellness benefits tailored to meet your needs. Choose from two medical plan options, including a company‑funded HSA plan with 100% premium coverage for employees. We also provide subsidized options for additional family members, as well as dental and vision plan choices. Other benefits include paid time off, paid volunteer time, and company‑paid holidays, a 401(k) match, employer‑paid life and AD&D insurance, and educational reimbursement to support your growth.
A job that challenges you—Middleburg strives for excellence in knowledge, service, and integrity. Excellence in knowledge means that Middleburg recruits and trains top‑notch team members who are experts in their field and who continue to improve their industry knowledge. Team members work together to provide excellent customer service that exceeds customers' expectations.
Great culture—We embrace a culture of responsible leadership at all levels of our organization that encourages initiative to advance our mission and vision. We honor the dignity of all people, embrace differences, value new ideas, demonstrate empathy, and strive to promote a caring and supportive environment for all. Our team is building a better world, one community at a time.
Middleburg Communities is an equal‑opportunity employer committed to diversity and inclusion. We welcome qualified applicants from a variety of backgrounds inclusive of their race, color, religion, sexual orientation, gender, gender identity, expression or orientation, genetic information, national origin, age, disability, or status as a disabled or Vietnam‑era veteran.
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This position can be based out of Tampa FL, Orlando FL, Raleigh NC, Charlotte NC, or Richmond VA.
Essential Duties And Responsibilities Portfolio Performance
Serve as leader for assigned communities, providing support and empowerment on leasing, sales, and marketing strategy, expense management, unit acceptance, staffing structure, and service delivery
Quickly and proactively diagnose and anticipate performance gaps (conversion, closing, lead generation, occupancy dips, NOI, customer experience, compliance) and develop clear, actionable improvement plans to which onsite teams are held accountable
Translate asset management strategy into executable onsite tactics
Operational Execution
Lead targeted interventions at underperforming or transitioning assets (lease‑ups, staffing resets, ownership transitions)
Support implementation and compliance of SOPs, systems, and new initiatives, ensuring consistency and adoption at the site level
Partner with onsite leadership to elevate operational rigor, accountability, decision‑making, and sales performance
Pre‑Operations Services
Assist Operations leadership in advising on rents, budgets, unit mix, design, and marketing for proposed developments
Cross‑Functional Partnership
Act as a bridge between Operations, Asset Management, Marketing, and partners/ownership
Support ownership/partner and leadership communication and site‑level readiness for investor interactions as needed
Travel & Field Presence
Maintain a high field presence, traveling frequently to assigned communities and/or development sites and submarkets
Be hands‑on and visible onsite and in markets—this role is not desk‑based
Requirements Knowledge and Experience
Undergraduate degree with a concentration in real estate, finance, strategy, operations, marketing, or entrepreneurship (MBA preferred)
4–7 years of experience with progressive leadership responsibility in real estate, hospitality, franchise operations, consulting, investment management, operations; exposure to asset‑level decision‑making strongly preferred
Experience managing teams—developing top performers and counseling under‑performers, ability to quickly identify and address personnel issues
Strong financial and analytical foundation, including comfort with underwriting assumptions, pro‑formas, operating budgets, revenue drivers, and translating financial insights into actionable operations
Demonstrated ability to effect positive performance results, moving seamlessly between data analysis, field execution, team management and motivation, and stakeholder management
Comfort with ambiguity and imperfect information; able to form hypotheses, test solutions in real time, and make sound recommendations without extensive oversight
Executive presence and communication maturity beyond years of experience; capable of interacting directly with ownership, asset management partners, and senior leadership, and onsite teams with confidence and credibility
Hands‑on orientation—intellectually curious but not desk‑bound; eager to be onsite, understand frontline operations, and see strategies executed in the real world
High standards and resilience; able to absorb feedback, handle pushback, and operate in a KPI and performance‑driven environment
Strong judgment, discernment, and integrity, particularly in owner‑facing or sensitive portfolio situations
Highly organized self‑starter with the ability to manage multiple priorities across a small portfolio of geographically dispersed assets
Willing and able to travel extensively and on short notice, with enthusiasm for field work and exposure to multiple markets and diverse asset types
What we can offer you
Great benefits—comprehensive health and wellness benefits tailored to meet your needs. Choose from two medical plan options, including a company‑funded HSA plan with 100% premium coverage for employees. We also provide subsidized options for additional family members, as well as dental and vision plan choices. Other benefits include paid time off, paid volunteer time, and company‑paid holidays, a 401(k) match, employer‑paid life and AD&D insurance, and educational reimbursement to support your growth.
A job that challenges you—Middleburg strives for excellence in knowledge, service, and integrity. Excellence in knowledge means that Middleburg recruits and trains top‑notch team members who are experts in their field and who continue to improve their industry knowledge. Team members work together to provide excellent customer service that exceeds customers' expectations.
Great culture—We embrace a culture of responsible leadership at all levels of our organization that encourages initiative to advance our mission and vision. We honor the dignity of all people, embrace differences, value new ideas, demonstrate empathy, and strive to promote a caring and supportive environment for all. Our team is building a better world, one community at a time.
Middleburg Communities is an equal‑opportunity employer committed to diversity and inclusion. We welcome qualified applicants from a variety of backgrounds inclusive of their race, color, religion, sexual orientation, gender, gender identity, expression or orientation, genetic information, national origin, age, disability, or status as a disabled or Vietnam‑era veteran.
#J-18808-Ljbffr