Benefits Specialist

Role Overview

Human Resources (aka People Support) at Accolade

Our team is called People Support instead of Human Resources because we are more than just your typical HR department - we’re a progressive and agile team of tenacious, trusted advisors who deliver efficient and effective programs to our employees to further enable the company’s strategy to grow the business.  People are at the center of our business, so therefore our People Support team and work we do are at the center of everything we do at Accolade.  Join us and experience the unique workplace and culture that’s earned Accolade a coveted spot on the Top Workplaces of Philadelphia list for the last 5 consecutive years.


Role Overview

We’re looking for a compassionate, innovative, and experienced Benefits Specialist to provide hands on support our employees with ongoing benefits and/or claims questions, manage all leave of absences and worker’s compensation claims, as well as partner with a Benefits Manager to execute our benefits strategy.  Furthermore, this role will be looked to as the subject matter expert to know our benefits plans inside and out, lead new hire benefit orientations, support all open enrollment efforts, and be a back-up to providing the Acccolade service to our own employees. 

A Day in the Life...

A day in the life….

  • As a subject matter expert of our benefits, this role will be looked to as the ‘go-to’ resource to support our employees in understanding their benefit options throughout their careers at Accolade. Said more specifically, this role will be accountable for designing and delivering effective Benefit Orientation sessions, taking the lead on responding to ad hoc benefit and claims questions, and serving as a key support resource to employees through Open Enrollment.  Furthermore, this role will serve as a back-up to support our Accolade for Accolade service as needed.
  • As the owner of our Leave of Absence programs (Disability, FMLA, Worker’s Compensation, Time Off), this role will be responsible for creating streamlined processes, tools and resources to seamlessly manage all LOAs from start to finish from an employee, leader, and People Support perspective. This includes and is not limited to identifying and implementing process improvement opportunities, as well as surfacing new LOA trends (i.e. increased Bereavement Leave) and making recommendations aligned with our business and total rewards priorities to enhance our programs.
  • Acts as right hand support to our Benefits Manager with all things related to the administration of benefits plans, Workday benefits processes, and managing vendor partner relationships. Owns Vendor Partner billing reconciliation to ensure our invoices are accurate and paid on a timely basis.
  • In partnership with the Benefits Manager, analyzes current trends to recommend enhancements and/or changes to our benefits program. Supports the execution of all Open Enrollment efforts including developing a project plan and drafting communications. 


Have demonstrated education, skills and experience to be successful in this role

  • Bachelor's degree in Human Resources, business, or related field required.
  • Minimum of 5-8 years of experience in roles related to Health & Welfare administration. CEBS, CBP, and experience in a high-touch service related environment both internally and externally is preferred.
  • This isn’t your first time at the rodeo: You have deep knowledge of laws, regulations, and government policy as they relate to health and welfare.  You have a strong understanding of benefits policies, procedures and practices including ACA, ERISA, IRS, Department of Labor and other employment law implications for benefit programs.  You have experience with vendor partner management. 
  • You’re compassionate and connected to our mission: You operate from a perspective of truly caring about our employees, clients, and customers and creating value for them. We are an innovative company looking for an innovative team member who will help us achieve best in class benefit programs and an awesome employee experience.
  • You’re known for your professionalism and respect for confidentiality: You uphold trust and confidentiality to the highest of standards in everything you do to support our employees.
  • You’re a critical and solutions focused thinker: You demonstrate a keen ability to quickly determine the proper course of action to resolve complicated and/or escalated employee issues or questions.
  • You’re flexible and energized by change: You prefer a fast-paced and dynamic environment and are agile and comfortable enough to keep up as plans change and evolve. 
  • You’re a multi-tasking machine: You’ve demonstrated the ability to balance and manage multiple priorities with accuracy, efficiency, and in a timely manner due to your strong organization skills.
  • You’re a self-starter: You take initiative and are comfortable being empowered to work independently. When you need help, you’re not shy to ask.  You proactively identify process inefficiencies and cost reductions to promote and support a continuous improvement philosophy and service culture.
  • You get things done: You follow through on every request, no matter how big or small, with attention to detail and the appropriate sense of urgency. You ensure projects in your area of responsibility meet quality, schedule, milestone, and budget commitments.
  • You’re tech savvy: Demonstrated experience using an HRIS (Workday preferred) and advanced skills in working with all programs in the Microsoft suite, especially excel, to simplify and propel your work.
  • You collaborate: You’re the consummate team player, able to build strong relationships and effectively partner with other team members to achieve results.
  • You’re a communication pro: You can speak and write in a clear, concise and professional manner. You have a demonstrated ability to read, analyze and interpret report and policies, as well as the ability to write proposals and policies.

Who we are

Values we admire:

  • We find joy and purpose in serving others.
    • Making a difference is what we do. We do the right thing for the right reasons – and we do it well, even when it’s hard.
    • You operate from a perspective of truly caring about our employees.
  • We are strong individually and together, we’re powerful.
    • We believe in each other, in honesty, and in having fun. You won’t find egos or office walls here because we aren’t defined by titles – but by actions, behaviors and results.
  • We roll up our sleeves and get stuff done.
  • We’re boldly and relentlessly reinventing healthcare.
    • We are a company changing the world, one person at a time.
    • Super high expectations? Bring it on? Our curiosity drives us.
  • You understand our desire to be the best place to work and that trust is the foundation of that.


Where it all began…

Accolade is an on-demand healthcare concierge for employers, health plans, health systems and consumers. Our team of compassionate, exceptional professionals is supported by breakthrough science and technologies to guide people through the healthcare system in a deeply personalized manner. By taking the time to get to know each person, understand the context of their healthcare decisions, build trust and influence decisions, we deliver industry-leading engagement levels, satisfaction scores unseen in healthcare, better health outcomes, and cost savings of more than 10 percent.


Accolade has been recognized as one of the nation’s 25 most promising companies by Forbes magazine, the fastest-growing private healthcare company by Inc. 500 and a Top Workplace in Philadelphia for five consecutive years. For more information, visit



Meet Some of Accolade's Employees

Lara E.

Customer Partnerships Manager

Lara ensures that every Accolade customer, whether an employer or health plans partner, understands the value of Accolade services—and gets the best service possible.

Courtney S.

Senior Manager, Talent Management

As a leader on the People Support Team, Courtney is dedicated to doing everything she can to make Accolade the best place to work.

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