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Benefits and People Operations Specialist

About the Role:

CaaStle is seeking a detail-oriented and experienced Benefits & People Operations Specialist to join our People Operations and Total Rewards team. Reporting to the Associate Director of People Operations, the Benefits & People Operations Specialist will manage CaaStle’s health and wellness benefits programs ensuring compliance with state, local, and federal applicable laws. In addition to owning the daily administration of our benefit programs, you will partner with the broader People Team to deliver center-of-excellence and shared services support. 

In this role, you will be owning the accuracy and compliance of our comprehensive benefits programs, ensuring our employees receive the support they need. You will be a subject matter expert, providing guidance on health, wellness, retirement, and leave policies, while maintaining meticulous records and ensuring regulatory compliance. 

As a key member of CaaStle's People Operations and Total Rewards team, you'll play a vital role in managing and enhancing our comprehensive benefits programs. Reporting to the Associate Director of People Operations, you'll ensure compliance, provide exceptional employee leverage, and contribute to the strategic development of our benefits offerings. This is an exciting opportunity to make a direct impact on our global team's well-being and satisfaction.

What you’ll do:

  • Proactively manage all aspects of our US benefit programs, including health, wellness, retirement, and leave programs.

  • Develop and maintain strong relationships with vendors to ensure accurate data transmission, timely claims processing, and adherence to service level agreements

  • Deliver exceptional support to employees, vendors, and internal teams, resolving inquiries and ensuring smooth operations including invoice processing.

  • Maintain data integrity of all employee records in our HRIS, Dayforce

  • Collaborate with payroll to reconcile benefit deductions and leave payments, ensuring alignment with employee records

  • Analyze market trends and employee data to suggest and implement improvements to the benefit program

  • Manage CaaStle’s immigration programs, including partnering with external counsel to ensure compliance with immigration laws and policies

  • Prepare ad hoc and routine reporting and compliance filing, such as EEO-1 annual filing 

  • Contribute to process improvement, documentation, and collaborative projects within the broader People Team 

We'd love for you to have:

  • 3 + years of Generalist experience 

  • 3 + years experience in US Benefits administration

  • Bachelor's Degree required

  • HRIS experience

  • Experience with US Payroll a plus

  • Knowledge of leave of absence administration processes and US state/federal legislation

  • Demonstrated analytical and data management skills along with superior attention to detail and problem-solving abilities

  • Strong analytical, communication, and collaboration skills.

Pay Range: $85,000 - $100,000

CaaStle is committed to equality of opportunity in employment. It has been and will continue to be the policy of CaaStle to provide full and equal employment opportunities to all employees and candidates for employment without regard to race, color, religion, national or ethnic origin, veteran status, age, sexual orientation, gender identity, or physical or mental disability. This policy applies to all terms, conditions and privileges of employment, such as those pertaining to training, transfer, promotion, compensation and recreational programs.

All employees must maintain appropriate handling of company confidential information(CCI) and personally identifiable information (PII). Complying with CaaStle information security policy. Ensuring that direct reports and contractors (if any) are adequately trained to comply with information security policy.

Average salary estimate

$92500 / YEARLY (est.)
min
max
$85000K
$100000K

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 and People Operations Specialist, CaaStle, Inc.

CaaStle is on the lookout for a talented Benefits and People Operations Specialist to join our vibrant People Operations and Total Rewards team in New York. This pivotal role will see you managing our health and wellness benefits programs and ensuring we remain compliant with a variety of laws and regulations. Reporting directly to the Associate Director of People Operations, your role will involve daily administration of our comprehensive benefit offerings. Beyond overseeing compliance, you'll become the go-to expert for health, wellness, retirement, and leave policies, always ensuring our team members receive the best possible support. You'll thrive in this position by building and maintaining strong relationships with vendors, which is essential for accurate data transfer and timely claims processing. We encourage your analytical skills as you explore market trends and employee data, making recommendations for enhancements to our benefits program. This role is not just about maintaining records; it’s about enhancing the overall employee experience, and your contributions will have a significant impact on well-being and satisfaction throughout CaaStle. Join us if you're ready to play a vital role in optimizing our benefits offerings and bringing our team to a new level of satisfaction and care.

Frequently Asked Questions (FAQs) for Benefits and People Operations Specialist Role at CaaStle, Inc.
What are the responsibilities of a Benefits and People Operations Specialist at CaaStle?

The Benefits and People Operations Specialist at CaaStle is responsible for managing all aspects of the US benefits programs, including health, wellness, retirement, and leave programs. This entails ensuring compliance with relevant laws, maintaining accurate employee records in the HRIS, and delivering exceptional support to both employees and vendors.

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What qualifications are required for the Benefits and People Operations Specialist position at CaaStle?

Candidates for the Benefits and People Operations Specialist position at CaaStle should have 3+ years of generalist experience in HR and benefits administration, along with a Bachelor's degree. Additionally, familiarity with HRIS systems and US payroll is a plus, coupled with strong analytical and communication skills.

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How does the Benefits and People Operations Specialist contribute to employee satisfaction at CaaStle?

By proactively managing and enhancing the benefits programs, the Benefits and People Operations Specialist plays a significant role in employee satisfaction at CaaStle. Their attention to detail ensures compliance and streamlined operations, directly affecting the well-being and support employees receive from their benefits.

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What is the pay range for the Benefits and People Operations Specialist position at CaaStle?

The pay range for the Benefits and People Operations Specialist position at CaaStle is between $85,000 and $100,000. This competitive salary reflects the importance of the role and the expertise required to effectively manage and enhance our benefits offerings.

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What kind of experience is beneficial for a Benefits and People Operations Specialist at CaaStle?

A successful Benefits and People Operations Specialist at CaaStle typically has experience in benefits administration, knowledge of US state and federal legislation, and demonstrated skills in analytical data management. Strong communication and collaboration skills are also essential in this role.

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Common Interview Questions for Benefits and People Operations Specialist
Can you explain your experience with benefits administration?

When answering this question, highlight specific responsibilities you've held in previous roles, the types of benefits you managed, and how you ensured compliance with relevant regulations. Provide examples that demonstrate your ability to exceed employee expectations in benefits support.

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How do you handle discrepancies in employee benefits records?

Your answer should emphasize your attention to detail and problem-solving skills. Explain a systematic approach you use to investigate discrepancies, the tools (like HRIS) you rely on to maintain data integrity, and your ability to communicate with involved parties to resolve issues.

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What strategies would you use to analyze benefits market trends?

Discuss your analytical methods for researching industry benchmarks, use of surveys, and how you interpret data to suggest enhancements. Highlight any tools you'd use for analysis, including HRIS or data visualization software, to make informed recommendations.

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Describe your experience collaborating with vendors for benefits administration.

Provide examples of past collaborations with benefits vendors where you ensured smooth operations, including managing claims processes and meeting service level agreements. Focus on the relationship management and communication skills you used to facilitate these partnerships.

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How do you ensure compliance with leave of absence policies?

Your response should detail your familiarity with leave legislation and the systems you’ve used to track leaves. Discuss how you educate employees about their rights and the steps you take to maintain accurate and up-to-date records in compliance with local and federal laws.

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Can you give an example of a process improvement you implemented in benefits administration?

Discuss a specific instance where you identified a gap in the benefits administration process and the data-driven approach you took to improve efficiency or employee satisfaction. Highlight the positive outcome and how you measured success post-implementation.

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What role does communication play in your job as a Benefits and People Operations Specialist?

Emphasize the importance of clear communication in benefits support. Talk about how you deliver complex information in an easily understandable manner to employees and how you facilitate discussions with management and vendors to keep operations streamlined.

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How do you handle confidential employee information?

Your answer should highlight your strict adherence to privacy protocols and data security measures. Discuss past experiences in managing sensitive information and the training practices you've employed to ensure compliance among your reports and contractors.

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What do you think is the most challenging aspect of managing benefits programs?

Discuss the various challenges, such as keeping up with changing legislation, ensuring effective communication with employees, or managing vendor relations. Emphasize your proactive approach to overcoming these challenges and your commitment to employee well-being.

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Why do you want to work for CaaStle as a Benefits and People Operations Specialist?

Speak to your alignment with CaaStle's values and culture. Share what particularly excites you about the opportunity, such as the company's commitment to employee satisfaction and opportunities for process improvement in their benefits programs.

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CaaStle is an innovative B2B technology and services company that enables apparel retailers and brands to offer their own rental experience directly to customers. CaaStle pioneered the subscription rental model in 2012 with its owned and operated ...

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Full-time, on-site
DATE POSTED
March 21, 2025

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