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Benefits & Leaves Manager

The Role

Prosper is seeking a dynamic and experienced Benefits & Leaves Manager to join our People

and Places team. In this role, you will manage and enhance Prosper's comprehensive health &

wellness programs, including our leave of absence program. We're looking for someone who is

curious, driven to understand and streamline current processes, committed to simplifying the

employee experience and ability to build and maintain strong partnership. The ideal candidate

excels at communicating complex concepts clearly and recognizes the profound impact benefits

have on employees' lives.


This is a hybrid role based at either our PHX or SF office.


Problems You Will Solve
  • Strategic Benefits Design: Manage the strategic design, implementation, and administration of Prosper's benefits offerings, including medical, dental, vision, life insurance, and disability plans.
  • Leave of Absence Program Management: Develop, refine, and manage Prosper's leave of absence program, policies, and processes. Manage the relationship with our outsourced leaves administrator, ensuring SOPs are created and SLAs are met. Develop manager and employee leave toolkits to educate on leave policies and processes, increasing awareness and compliance.
  • Open Enrollment Management: Lead the annual open enrollment process, ensuring smooth execution and effective communication to employees. Manage ADP benefits setup and ensure accurate data entry and system configuration.
  • Leave Support: Communicate with employees regarding their leave needs, ensuring they are aware of their responsibilities and the steps required to qualify for leave, providing a seamless and supportive experience.
  • Customer Service: Provide exceptional customer service to internal and external stakeholders as the primary point of contact for plan vendors, third-party consultants, and employees.
  • Employee Communication and Training: Manage internal communications, develop and deliver training programs for leaders and employees to improve understanding of benefits offerings.
  • Operational Efficiency: Identify and implement opportunities to improve operational efficiency within benefits and leave administration, including streamlining processes within ADP and other HR systems, enhancing the overall employee experience.
  • Vendor and Partnership Management: Partner with Finance, Legal, and People Teams to manage vendor contracts and implement new programs.
  • Wellness Initiatives: Develop and execute comprehensive wellness initiatives, including workshops, challenges, and partnerships, to promote employee wellbeing across all dimensions.
  • Regulatory Compliance: Maintain current knowledge of all applicable leave and accommodation laws (e.g., ERISA, HIPAA, FMLA, ACA, COBRA) and ensure plan compliance with regulatory filings, updates, notices, audits, and non-discrimination testing.


About You
  • Advanced knowledge in benefits plan design and administration (Level funded or self-insured plan management experience is preferred)
  • Extensive knowledge and experience with the leave requirements in multiple states (CA, NY, NJ ect.) and federal, state and local regulations (e.g. ERISA, HIPAA, FMLA, ACA, COBRA etc.)
  • Demonstrated ability to build and maintain strong relationships with internal and external stakeholders
  • Strong analytical skills with proficiency in Excel and Google sheets
  • Strong experience with multi-jurisdictional leave programs
  • Great organizational skills, high attention to detail
  • Excellent written and verbal communication skills
  • Strong problem-solving skills
  • Effective planning & priority setting
  • 8+ years of related benefits administration experience, including 5+ years of experience administering leaves of absence, Bachelor's Degree required.


What We Offer
  • The opportunity to collaborate with a team of creative, fun, and driven colleagues on products that have an immediate and significant impact on people's lives
  • The opportunity to work in a fast-paced environment with experienced industry leaders
  • Flexible time off, comprehensive health coverage, competitive salary, paid parental leave
  • Wellness benefits including access to mental health resources, virtual HIIT and yoga workouts
  • A bevy of other perks including Udemy access, childcare assistance, pet insurance discounts, legal assistance, and additional discounts


$119,000 - $160,000 a year
Compensation details:
The salary range is $119,000 - $160,000 annually, plus bonus and generous benefits. In determining your salary, we will consider your location, experience, and other job-related factors.

#LI-SK1


About Us

Founded in 2005 as the first peer-to-peer marketplace lending platform in the U.S., Prosper was built on a simple idea: connect people who want to borrow money with those who want to invest. Since inception, Prosper has helped more than 2 million people gain access to affordable credit with over $27 billion in loans originated through its platform. Our mission is to help our customers advance their financial well-being through a variety of products including personal loans, credit, home equity lines of credit (HELOC), and our newest product, HELoan. Our diverse culture rewards accountability and cross functional teamwork because we believe this encourages innovative thinking and helps us deliver on our mission.  

 

We’re on a mission to hire the very best, and we are committed to creating exceptional employee experiences where everyone is respected and has access to equal opportunity. We realize that new ideas can come from everywhere. It is important to us that every hire connects with our vision, mission, and core values. Join a leading fintech company that’s democratizing finance for all!  


Our Values

Diversity expands opportunities

Collaboration creates better solutions

Curiosity fuels our innovation

Integrity defines all our relationships

Excellence leads to longevity 

Simplicity guides our user experience 

Accountability at all levels drives results


www.prosper.com

Our Story & Team  //   Our Blog 


Applicants have rights under Federal Employment Laws.

Family & Medical Leave Act (FMLA)

Equal Employment Opportunity (EEO)

Employee Polygraph Protection Act (EPPA)  


California applicants: please click here to view our California Consumer Privacy Act (“CCPA”) Notice for Applicants, which describes your rights under the CCPA: https://www.prosper.com/plp/legal/privacy-notice-for-applicants/


At Prosper, we're looking for people with passion, integrity, and a hunger to learn. We encourage you to apply even if your experience doesn't precisely match the job description. Your unique skill set and diverse perspective will stand out and set you apart from other candidates. Prosper thrives with people who think outside of the box and aren't afraid to challenge the status quo. We invite you to join us on our mission to advance financial well-being.


Prosper is committed to an inclusive and diverse workplace. All aspects of employment including the decision to hire, promote, discipline, or discharge, will be based on merit, competence, performance, and business needs. We do not discriminate on the basis of race, color, religion, marital status, age, national origin, ancestry, physical or mental disability, medical​​​ condition, pregnancy, genetic information, gender, sexual orientation, gender identity or expression, veteran status, or any other status protected under federal, state, or local law, including the San Francisco Fair Chance Ordinance. Prosper will consider for employment qualified applicants who are non-US citizens and will provide green card sponsorship.

Average salary estimate

$139500 / YEARLY (est.)
min
max
$119000K
$160000K

If an employer mentions a salary or salary range on their job, we display it as an "Employer Estimate". If a job has no salary data, Rise displays an estimate if available.

What You Should Know About Benefits & Leaves Manager, Prosper

Are you looking to make a significant impact in the world of employee benefits? Prosper is on the hunt for a passionate Benefits & Leaves Manager to join our People and Places team! In this role, you’ll oversee Prosper's comprehensive health and wellness programs, including our leave of absence initiatives, while elevating the employee experience. You’ll be the driving force behind our benefits strategy, from the design and administration of medical, dental, and vision plans to managing our outsourced leave administration. We value curiosity and efficiency, so you'll have the opportunity to analyze current processes and implement streamlined solutions. Strong communication skills are key as you educate employees about their leave options and provide assistance around their benefits. You’ll also manage the open enrollment process and ensure that employees clearly understand their options. Collaboration is essential here at Prosper; you’ll forge strong relationships with internal and external stakeholders and work hand in hand with our Finance and Legal teams. We're committed to promoting employee wellness, so you'll develop and execute initiatives that resonate with our team members. If you have extensive experience in benefits plan administration, particularly in multi-jurisdictional leave regulations, and a talent for delivering exceptional customer service, we’d love to hear from you. Join us in our mission to enhance financial well-being, and enjoy a vibrant company culture that emphasizes accountability, diversity, and innovative thinking.

Frequently Asked Questions (FAQs) for Benefits & Leaves Manager Role at Prosper
What responsibilities does the Benefits & Leaves Manager at Prosper have?

As the Benefits & Leaves Manager at Prosper, you will be responsible for overseeing and enhancing benefits offerings, including medical, dental, and leave of absence programs. Your role includes managing strategic benefits design, leading the open enrollment process, communicating effectively with employees about their leave rights, and ensuring compliance with regulations such as FMLA and ACA.

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What qualifications are needed for the Benefits & Leaves Manager position at Prosper?

To qualify for the Benefits & Leaves Manager role at Prosper, candidates should have at least 8 years of experience in benefits administration, including 5 years focused on leaves of absence. A Bachelor’s degree is required, along with advanced knowledge of benefits design, strong analytical skills, and excellent communication abilities.

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How does Prosper ensure compliance with benefits regulations in the Benefits & Leaves Manager role?

In the Benefits & Leaves Manager role at Prosper, compliance is maintained by staying updated on federal, state, and local regulations, including the FMLA and ACA. You will also oversee ongoing audits and regulatory filings, ensuring that all policies and procedures are up to date.

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What can a Benefits & Leaves Manager expect in terms of company culture at Prosper?

At Prosper, a Benefits & Leaves Manager can expect to thrive in a collaborative, innovative, and diverse work environment. We emphasize accountability, cross-functional teamwork, and a passion for learning, allowing you to connect with colleagues who share your commitment to creating exceptional employee experiences.

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Is remote work an option for the Benefits & Leaves Manager position at Prosper?

Yes! The Benefits & Leaves Manager position at Prosper offers flexibility as it is a hybrid role, allowing for a combination of in-office and remote work based on your location, which can be either our PHX or SF office.

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Common Interview Questions for Benefits & Leaves Manager
What strategies would you implement to improve the benefits program at Prosper?

To improve the benefits program at Prosper, I would first conduct an employee needs assessment to understand current sentiments about our offerings. Following this, I would collaborate with stakeholders to identify areas for enhancement, focusing on introducing wellness initiatives and streamlining communications about benefits.

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How do you manage vendor relationships effectively?

To manage vendor relationships effectively, I prioritize open communication, ensuring regular check-ins to discuss performance and address any concerns. Building rapport is crucial; I aim to align vendor capabilities with our company goals, ensuring that our needs are met efficiently.

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Can you describe your experience with leave of absence programs?

In my previous roles, I have managed various leave of absence programs, ensuring compliance with applicable laws and providing clear guidance to employees. Creating toolkits for managers and offering educational sessions helped enhance understanding and compliance within the organization.

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What is your approach to open enrollment management?

My approach to open enrollment management involves proactive planning and clear communication. I work on creating engaging materials to inform employees about their choices and ensure that all systems are well configured and data is accurately entered to prevent disruptions.

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How do you stay updated on benefits regulations?

I stay updated on benefits regulations by actively participating in industry webinars, following relevant newsletters, and being involved in professional HR organizations. Networking with peers also provides insights into changes and best practices within the field.

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How would you educate employees about their leave options?

Educating employees about their leave options involves creating accessible resources such as FAQs and one-on-one consultations. I also recommend hosting informative workshops to explain policies clearly and answer any questions that employees may have.

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What tools do you use for benefits administration?

I typically use HR information systems like ADP for benefits administration. Proficiency in Excel and Google Sheets is essential for managing data effectively, analyzing trends, and generating reports to inform strategic decisions.

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Describe a challenge you've faced in benefits administration and how you overcame it.

One challenge I faced was transitioning to a new benefits platform. To overcome this, I developed a detailed project plan, involving stakeholders early to gather feedback and address concerns, ensuring a seamless transition and minimal disruption for employees.

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What skills are essential for a Benefits & Leaves Manager?

Essential skills for a Benefits & Leaves Manager include strong analytical abilities, exceptional communication, and organizational skills, along with a deep understanding of benefits regulations and employee needs. Problem-solving and the ability to build relationships are also vital.

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How do you promote wellness initiatives within a company?

Promoting wellness initiatives involves collaborating with different team members to create engaging activities that resonate with employees. I focus on campaigns that cover various aspects of well-being, such as physical health, mental wellness, and lifestyle changes, ensuring we have something for everyone.

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Prosper Marketplace, Inc. was founded in 2005 and is headquartered in San Francisco. The lending platform is owned by Prosper Funding LLC, a subsidiary of Prosper Marketplace, Inc. Loans originated through the Prosper marketplace are made by WebBa...

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Full-time, hybrid
DATE POSTED
April 20, 2025

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