Assistant Director, Leave and Accommodation

Company Overview 

Asset Living is a third-party management firm with a proven partner in fostering thriving communities nationwide. Founded in 1986, Asset Living has decades of experience delivering exceptional value to our partners. Since the beginning, our undeniable passion has driven our organic growth from a small property management firm to one of the most trusted allies in real estate. Asset Living's growing portfolio includes a multitude of properties across the country that span the multifamily, single-family home rentals, affordable housing, build-to-rent, active adult, and student housing divisions.   

Asset Living is a fast-growing company made up of talented individuals from diverse backgrounds that differentiate us and help us drive innovation and results for our clients and communities across the US. At Asset Living, we wholeheartedly believe 'Together We Lead, Together We Succeed. We empower each other to lead by example, collaborate, and evolve – inspired by our belief that we can continually improve as individuals and as an organization. Together, we create an environment where every voice is heard, every idea is valued, and every individual experiences opportunities to grow as our company grows. When you join Asset Living, you become part of a dynamic team that thrives on unity, unique talents, and a universal culture of winning.    

Recognized as one of the nation's Best and Brightest Places to Work and ranked in the NMHC top 50 professionals, join Asset Living because of its reputation as the most trusted partner in real estate, workplace culture, and growth opportunities. Asset Living is a member of The Institute of Real Estate Management (IREM) and is recognized as an Accredited Management Organization (AMO). Together, we lead the way, and together, we achieve excellence in all that we do. Join a workplace where success is a collective journey and leadership is a shared responsibility.   

Assistant Director, Leave and Accommodation

The Assistant Director, Leave and Accommodation provides leadership and operational oversight for the organization’s leave of absence and workplace accommodation programs. The Assistant Director leads complex case strategy, serves as an escalation point for high-risk or sensitive matters, and partners with employees, operational leaders, Human Resources, Benefits, Payroll, Employee Relations, third-party administrators, and Legal.

This position directly supervises the Leave & Accommodations Specialists and is accountable for caseload oversight, work allocation, quality review, coaching, process improvement, reporting, and program governance. The Assistant Director also maintains an assigned caseload of complex matters and provides practical guidance when leave or accommodation issues intersect with performance, attendance, discipline, organizational changes, return-to-work planning, or separation decisions.

Essential Duties & Responsibilities

• Lead the day-to-day administration of leave and accommodation programs, establish service expectations, monitor workflows, and promote consistent practices across the organization.
• Directly supervise the Leave & Accommodations Specialist, including assigning work, reviewing case strategy and documentation, providing coaching and training, monitoring deadlines and service levels, and supporting professional development.
• Independently manage and provide direction on high-risk or complex cases involving extended or indefinite leave, intermittent leave, medical restrictions, pregnancy-related limitations, mental health conditions, overlapping protections, alternative placement, hardship considerations, and disputed documentation or determinations.
• Guide and document the ADA interactive process; evaluate requested accommodations and effective alternatives; coordinate implementation; assess operational impact and potential undue hardship; and partner with Legal on sensitive or unresolved matters.
• Oversee eligibility, certification, designation, extensions, recertification, exhaustion, reduced schedules, military leave, state paid leave programs, personal leave, disability-related matters, and return-to-work requirements under applicable federal, state, local, and company programs.
• Serve as the primary escalation point when protected leave or accommodation matters intersect with performance management, attendance, discipline, retaliation concerns, organizational changes, or proposed separation. Identify risk and recommend compliant, practical next steps.
• Provide clear, compassionate, and practical guidance regarding employee responsibilities, documentation requirements, timelines, restrictions, available options, and company processes. Coach leaders on maintaining confidentiality and avoiding interference, retaliation, or inconsistent treatment.
• Manage relationships with third-party leave and accommodation administrators, monitor claim handling and service quality, address discrepancies, and coordinate with Benefits, Payroll, Employee Relations, HR leadership, Safety, and Legal.
• Oversee return-to-work planning, medical releases, restrictions, modified duty, transitional work, schedule changes, accommodation implementation, alternative placement considerations, and related stakeholder communication.
• Conduct routine audits of leave and accommodation files, intermittent leave usage, reduced schedules, documentation, designations, restrictions, status changes, and return-to-work activity. Correct gaps and use findings to improve processes and training.
• Develop and maintain reporting on caseload volume, aging, response times, leave types, accommodation activity, return-to-work outcomes, vendor performance, trends, and areas of compliance or operational risk.
• Develop and maintain policies, procedures, templates, resources, manager guidance, and training. Monitor legal and regulatory developments and recommend updates to practices and communications.
• Ensure leave status, return dates, timekeeping, pay-related changes, benefit considerations, restrictions, and employee records are communicated and processed accurately and timely in applicable systems.
• Maintain complete, accurate, and confidential case records, including medical documentation, correspondence, approvals, restrictions, timelines, analyses, and decisions. Limit access to sensitive information based on business need.
• Partner with HR and operational leaders to evaluate staffing impacts, temporary coverage, workforce planning, and business continuity associated with leaves and accommodations.
• Support broader HR compliance initiatives, special projects, audits, acquisitions or transitions, and other duties as assigned.

Education & Experience 

• Bachelor’s degree in Human Resources, Business Administration, or a related field preferred. Equivalent relevant experience may be considered.
• Five or more years of progressive Human Resources experience preferred, including substantial direct experience with leave administration and workplace accommodations. Prior leadership, team-lead, or supervisory experience strongly preferred.
• Advanced working knowledge of FMLA, ADA, USERRA, pregnancy-related accommodation requirements, state and local leave laws, paid leave programs, disability benefits coordination, and the interactive accommodation process.
• Demonstrated ability to administer leave and accommodation matters across multiple jurisdictions and identify when state or local requirements provide additional protections.
• Ability to set expectations, prioritize team workloads, coach performance, review work product, resolve escalations, and build consistent and accountable practices.
• Strong critical-thinking and decision-making skills, including the ability to analyze medical and operational information, distinguish routine from high-risk matters, and escalate appropriately.
• Excellent written and verbal communication skills with the ability to explain sensitive or complex requirements clearly and professionally to employees and leaders at all levels.
• Ability to manage a high-volume and complex caseload while overseeing team deliverables, competing deadlines, audits, projects, and timely follow-up.
• Ability to analyze trends, maintain meaningful metrics, evaluate vendor performance, and translate findings into practical process improvements.
• Demonstrated discretion in handling medical information and other sensitive employee records in accordance with confidentiality requirements.
• Proficiency in Microsoft Office Suite and experience with HRIS, case-management, ticketing, payroll, benefits, or leave-administration systems.
• Ability to remain calm, professional, empathetic, and solutions-oriented during difficult conversations and in a fast-paced, changing environment.

This job description should not be considered all-inclusive. It is merely a guide of expected duties. The employee understands that the job description is neither complete nor permanent and may be modified at any time. At the request of their supervisor, an employee may be asked to perform additional duties or take on additional responsibilities without notice. 

#LI-Remote

Asset Living is required by law to include a reasonable estimate of the compensation range for this role. This compensation range is specific to the remote nature of this position and includes the range of factors considered in making compensation decisions including but not limited to skill sets; experience and training; certifications; etc. We would not anticipate that the individual hired into this role would be near the top end of the compensation range, but that decision will be dependent on the facts associated with each specific individual’s relevant experience for the role.  A reasonable estimate of the range is below.

Remote Pay Range$75,000—$85,000 USD