Senior Leave Specialist

Evolve

1d•$75,680 - $94,600•Remote

About The Position

At Evolve, we’re on a mission to make vacation rental easy for everyone. Our high-performing, customer-obsessed team runs on curiosity, communication, and accountability—working together to create exceptional experiences for our owners and guests. Whether solving big challenges, delivering outstanding results, or celebrating wins, we approach every day with purpose and passion. If you’re ready to join a mission-driven company where every teammate has the opportunity to thrive, Evolve might just be the place for you. Why this role The Leave Specialist will own the administration of all employee leaves of absence, including FMLA, state-specific leaves, ADA accommodations, and related time away programs. This role will act as a key liaison between employees, managers, vendors, and internal stakeholders to ensure leaves are handled accurately, empathetically, and in compliance with applicable laws. This role is highly employee-facing and requires strong judgment, communication skills, and comfort navigating sensitive situations. The environment is complex and evolving, with employees in all 50 states and a mix of established and developing processes. We are looking for someone who can sift through ambiguity and noise, bring clarity and structure, and help simplify and standardize leave practices over time.

Requirements

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)

Nice To Haves

Preferred: PHR/SPHR (Professional in Human Resources/Senior Professional in HR)

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

Benefits

Financial Wellness: Industry-competitive pay, equity in the company, and a 401(k) with a 4% immediate vesting match.
Family Support: 16-18 weeks of paid parental leave for birthing parents and 10 weeks for non-birthing parents, plus infertility coverage.
Health & Wellness: Comprehensive medical, dental, and vision plans (100% employer-paid for individual enrollment), 10 free mental health visits, and pet insurance.
Time to Recharge: Generous PTO, RTO (for full-time exempt employees), sick leave, holidays, and a personal holiday to celebrate what matters most to you.
Travel Perks: Annual Evolve travel credit after one year and discounts on stays at all Evolve properties.
Growth Opportunities: World-class onboarding programs, learning, and development resources to help you grow your impact.
Connection: Employee Resource Groups celebrating our diverse communities at Evolve.

Stand Out From the Crowd

Upload your resume and get instant feedback on how well it matches this job.

Upload and Match Resume