Senior Leave Specialist

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.

What you’ll do 

• 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

What makes you a great fit 

• 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)

Compensation

Annual base salary range: $75,680 to $94,600, depending on relevant experience.

Location 

All Evolve team members must live in one of our approved locations by their first day. We can hire from anywhere in the U.S. except D.C. and Hawaii. Some positions may also have restrictions based on compensation in the following states: California, Maryland, New York, Pennsylvania, Rhode Island, and Washington. If you live in Colorado, you can work remotely anywhere in the state, at our downtown Denver office, or a hybrid of both! If you're planning to move soon, please let us know, and we'll be happy to review your application again.

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How we reward Evolvers

We’re intentional about offering benefits that empower every Evolver to thrive both professionally and personally because they’re more than perks—they’re investments in our customer-obsessed, high-performing team.

We believe in treating others as they want to be treated, providing benefits that deliver real value, and challenging the status quo to meet the diverse needs of our team. Whether it’s helping you