Evolve · 1 week ago
Senior Leave Specialist
United States
Full-time
Remote
Mid, Senior Level
$76K/yr - $95K/yr
4+ years expEvolve is on a mission to make vacation rental easy for everyone. The Senior Leave Specialist will manage employee leaves of absence and ensure compliance with applicable laws while acting as a liaison between employees and internal stakeholders.
HospitalityTourismTravelVacation Rental
Responsibilities
Administer all leaves of absence, including FMLA, state leaves, parental leave, medical leave, military leave, and personal leaves
Partner closely with our leave vendor(s) (e.g., Sun Life) to ensure accurate, timely processing and documentation
Serve as the primary point of contact for employees and managers throughout the leave lifecycle
Ensure compliance with federal, state, and local leave laws
Translate complex federal and state leave requirements into clear, employee-friendly guidance and scalable internal practices
Maintain accurate leave records in HRIS
Educate employees and managers on leave policies, processes, and expectations
Identify gaps, inefficiencies, or risks in leave processes and recommend improvements
Build strong working relationships across People Ops, Legal, Payroll, and leadership
Handle sensitive information with discretion, empathy, and professionalism
Qualification
Required
4–6+ years of experience administering leaves of absence and accommodations in a multi-state environment
Comprehensive working knowledge of FMLA and state leave programs (e.g., CO, CA, NY, WA strongly preferred)
Experience advising employees and managers on leave eligibility, documentation, and return-to-work coordination
Proven experience partnering with third-party leave vendors and managing complex cases
HRIS experience required; Rippling experience a strong plus
Ability to analyze leave requests, determine eligibility, and manage accurate time/pay adjustments in HRIS or payroll systems
Strong communication and relationship-building skills with employees, managers, and senior stakeholders
Demonstrated ability to receive, process, and apply feedback in a fast-changing environment
Highly organized, detail-oriented, and comfortable working independently with minimal supervision
Exposure to broader work-life, flexibility, or family-support programs (e.g., accommodations, EAP, flexible work arrangements)
Preferred
PHR/SPHR (Professional in Human Resources/Senior Professional in HR)
Benefits
Industry-competitive pay, equity in the company, and a 401(k) with a 4% immediate vesting match.
16-18 weeks of paid parental leave for birthing parents and 10 weeks for non-birthing parents, plus infertility coverage.
Comprehensive medical, dental, and vision plans (100% employer-paid for individual enrollment), 10 free mental health visits, and pet insurance.
Generous PTO, RTO (for full-time exempt employees), sick leave, holidays, and a personal holiday to celebrate what matters most to you.
Annual Evolve travel credit after one year and discounts on stays at all Evolve properties.
World-class onboarding programs, learning, and development resources to help you grow your impact.
Employee Resource Groups celebrating our diverse communities at Evolve.
Company
Evolve
Evolve offers rental services for vacation with modern approach to hospitality and property.
501-1000 employees
Funding
Current Stage
Late StageTotal Funding
$224.2MKey Investors
Durable Capital PartnersT. Rowe PriceRobert Mylod Jr.
2022-02-14Series F· $100M
2020-05-29Series E· $25M
2018-08-23Series D· $80M
Leadership Team
Brian Egan
Co-Founder & CEO
Brian Becker
Chief Growth Officer
Recent News
UPSTATE BUSINESS JOURNAL
2025-12-12
2025-11-27
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