Trupp HR - Leave Administration Support Specialist (Remote/Full-Time)

Pay Range: $24-30 hourly
Status: Non-Exempt
Schedule: Monday through Friday, 9:00 a.m. to 6:00pm Pacific Time

Are you highly organized, detail-oriented, and interested in growing your career in leave administration? Do you enjoy keeping moving pieces on track, supporting employees through sensitive situations, and making sure documentation, deadlines, and follow-up stay on course? Ready to build your HR experience in a fully remote, values-driven environment? Say goodbye to the mundane and join an innovative team that boldly colors outside the lines!

At Trüpp, we believe in harnessing the power of our collective team—valuing the diverse talents, strengths, perspectives, backgrounds, and even quirky traits of each of our employees. As a fully remote organization, Trüpp is committed to creating a work environment where all team members feel welcome, respected, supported, and valued.

The Leave Administration Support Specialist plays an important role in supporting leave administration services for clients located throughout the U.S. This position assists the Leave Administration team with leave intake, document processing, data entry, routine follow-up, case coordination, and workflow tracking. The role helps ensure leave cases are complete, organized, accurately documented, and routed to the appropriate Leave Specialist for review in accordance with internal processes, compliance requirements, and client-specific guidelines.

This is a great opportunity for someone early in their leave administration or HR career who wants to build foundational experience in leave processes, compliance support, case documentation, and employee service.
Successful candidates will thrive in a small, energetic team environment; excel at detail-oriented and deadline-driven work; manage high-volume administrative tasks across multiple systems; communicate clearly and empathetically; stay organized through changing priorities; protect confidential information; and consistently deliver accurate, timely, high-quality work.

WHAT YOU’LL DO

• Monitor, triage, and route incoming leave requests, emails, system queues, documents, and related case activity based on established workflows, priority, client process, and urgency.
• Support leave case setup and administration by entering employee and case information, updating case details, maintaining notes, tracking tasks, and keeping case records accurate, organized, and complete.
• Review, categorize, upload, and attach leave-related documentation; track receipt of required materials and route documentation to Leave Specialists for review.
• Gather and organize relevant employee and case information needed to support eligibility review, including HRIS data, payroll information, employment status, work location, leave history, and related details.
• Provide standard information to employees regarding leave-related forms, deadlines, documentation requirements, and next steps using approved templates and communication guidelines.
• Conduct routine follow-up on missing documentation, incomplete forms, upcoming deadlines, return-to-work needs, and other time-sensitive case activity.
• Identify missing, incomplete, inconsistent, or unclear information and escalate questions, discrepancies, urgent matters, complex issues, or sensitive situations to the appropriate Leave Specialist.
• Assist with shared inbox management, incoming calls, task tracking, reporting support, workflow organization, and other administrative activities that help ensure leave cases move forward accurately and efficiently.

WHAT’S IN YOUR TOOLBOX

• Foundational knowledge of FMLA, multi-state leave regulations, leave administration processes, and related HR practices.
• Strong attention to detail with the ability to identify missing, incomplete, inconsistent, or unclear information.
• Excellent organization, time-management, and prioritization skills in a high-volume, deadline-driven environment.
• Clear, professional, and empathetic communication with employees, clients, internal team members, and other stakeholders.
• Proficiency with Microsoft Office and comfort learning HRIS platforms, case management systems, ticketing tools, shared inboxes, and document management tools.
• Commitment to confidentiality, professionalism, Trüpp’s core values, and delivering accurate, timely, high-quality work.

WHAT GOT YOU HERE

• Associate’s degree in Human Resources, Business, or a related field—or equivalent experience.
• 1–2 years of leave administration or related HR experience.
• Basic knowledge of FMLA and multi-state leave regulations.
• Strong attention to detail, accuracy, and ability to identify missing, incomplete, or inconsistent information.
• Ability to manage high-volume, deadline-driven work while balancing multiple priorities in a fast-paced environment.
• Strong organization, prioritization, and time management skills, including the ability to adapt to changing priorities and workflows.
• Strong customer service orientation with clear, professional, and empathetic communication skills.
• Ability to follow structured processes, workflows, and instructions while working independently and escalating appropriately.
• Comfort working across multiple systems, such as HRIS platforms, case management systems, ticketing tools, shared inboxes, and document management platforms.
• Ability to handle confidential and sensitive employee information with discretion.

A LITTLE ABOUT TRÜPP
Trüpp (Swedish for “team” and pronounced as “troop”) was founded in 2011 and is recognized as one of Oregon and SW Washington’s Top 50 Women-Owned Businesses. Providing HR Outsourcing and Consulting services to small and mid-sized employers nationwide, we are a collaborative team of professionals, passionate about helping our clients thrive. 


WHAT YOU’LL GET
Trüpp values its employees! Our team members enjoy the following benefits:

• Flexible work schedule and 100% remote work environment that fosters coworker collaboration and teamwork
• $500 per year workplace stipend
• Education reimbursement program
• Generous paid time off program and 12 paid holidays
• Medical, dental, and vision insurance, with a significant portion of employee coverage paid by the employer, as well as buy-up options and the option to extend coverage to employee dependents/spouse/partner
• 401(k) with up to 4% company match
• Voluntary benefits such as FSA accounts, short-term and long-term disability, and group life insurance

Trüpp is committed to attracting and retaining a diverse staff and will honor all individual experiences, perspectives, and unique identities. Together, we strive to create and maintain a working environment that is inclusive, equitable, and welcoming.