Stride
Benefits Director
🇺🇸 Remote - US
🕑 Full-Time
💰 $113K - $155K
💻 Human Resources
🗓️ October 23rd, 2025
Edtech.com's Summary
Stride, Inc. is hiring a Benefits Director to develop, implement, and manage comprehensive employee benefits programs that support organizational objectives and enhance employee well-being. The role requires crafting benefits strategies, overseeing health and welfare plans, retirement programs, and compliance, while leading a team and managing vendor relationships to ensure cost-effectiveness and competitive positioning.
Highlights
- Develop and execute benefits strategies for health, welfare, retirement, wellness, and leave programs.
- Lead cross-functional initiatives and manage the annual Open Enrollment process.
- Manage relationships with benefits brokers, carriers, and third-party vendors.
- Monitor legislative changes and ensure regulatory compliance, including government filings and disclosures.
- Collaborate with Finance to forecast and control benefit budgets and costs.
- Lead and mentor a team of 1-5 employees, including hiring, training, and performance management.
- Require 10 years of experience in benefits administration with 5 years in people management.
- Proficient in Microsoft Outlook, Word, PowerPoint, Project, Visio, advanced Excel, and HRIS benefit modules (Workday, Ultimate Software, Oracle).
- Salary range is $113,480.25 to $155,000 per year, with possible bonuses and robust benefits.
- Home-based position requiring successful background check and web proficiency.
Benefits Director Full Description
Job Description
SUMMARY: The Director, Benefits is a strategic leader responsible for designing, implementing, and managing comprehensive employee benefits programs that align with organizational goals and enhance employee well-being. This hands-on role requires both strategic vision and operational expertise to oversee health and welfare plans, retirement programs, leave policies, and wellness initiatives, ensuring compliance, cost-effectiveness, and competitive positioning in the marketplace.
ESSENTIAL FUNCTIONS: Reasonable accommodations may be made to enable individuals with disabilities to perform the essential duties.
- Develop and execute forward-thinking benefits strategies encompassing health, welfare, retirement, wellness, and leave programs, ensuring alignment with organizational goals and industry benchmarks.
- Lead cross-functional initiatives to enhance the employee experience through innovative benefits offerings.
- Oversee the strategic planning and execution of the annual Open Enrollment process, including renewal strategy, employee communications, and educational materials.
- Build and manage relationships with benefits brokers, carriers, and third-party vendors to optimize service levels, cost efficiency, and program effectiveness.
- Monitor legislative changes and assess their impact on benefit programs.
- Collaborate with Finance to forecast and manage benefit budgets.
- Analyze cost trends and recommend plan design changes to optimize value and control expenses.
- Develop clear communication strategies to educate employees on benefits offerings.
- Serve as a resource for escalated employee inquiries and complex case resolution.
- Lead and mentor a team of benefits professionals.
- Foster a culture of continuous improvement and service excellence.
- Oversee and ensure appropriate controls are in place to safeguard personnel data, maintain continuity of operations, and maintain data accuracy and integrity
- Maintain knowledge of HR requirements and regulations affecting human resources functions and ensures policies, procedures and reporting are in compliance
- Ensures plans are compliant with local, state and federal regulations, including timely and accurate completion of all required government filings, and distribution of required participant plan disclosures.
Supervisory Responsibilities:
- This position leads a team of up to 1-5 regular employees, interns and/or contractors. Carries out supervisory responsibilities in accordance with the organization's policies and applicable laws. Responsibilities include interviewing, hiring, and training employees; planning, assigning, and directing work; appraising performance; rewarding and disciplining employees; addressing complaints and resolving problems.
MINIMUM REQUIRED QUALIFICATIONS:
- Ten (10) years of progressive experience in benefits administration with five (5) years of people management experience.
- Deep knowledge of compensation analysis and benefits structures, and benefit regulations, including health care reform (Affordable Care Act - ACA), HIPAA, Workers Compensation, ERISA, etc.
- Excellent written and verbal communication skills
- Proven ability to organize and lead a project to completion
- Effective problem-solving, decision making and critical thinking skills
- Excellent interpersonal skills, with the ability to communicate sensitive and confidential matters effectively
- Ability to maintain strict confidentiality
- Proven success managing benefits strategies for an employee population of over 8,000 employees
- Focus on customer satisfaction
- Proficient in Microsoft Outlook, Word, PowerPoint, Project, and Visio; Intermediate to advanced Excel user.
- Experience with benefit module(s) of HRIS applications such as Workday, Ultimate Software, Oracle, etc.
- Web proficiency
- Ability to clear required background check
Certificates and Licenses: None required.
DESIRED QUALIFICATIONS:
- Bachelor's Degree in human resources or related field
- Attainment or pursuit of Certified Employee Benefit Specialist (CEBS)
WORK ENVIRONMENT: The work environment characteristics described here are representative of those an employee encounters while performing the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.
- This is a home-based position.
Compensation & Benefits: Stride, Inc. considers a person's education, experience, and qualifications, as well as the position's work location, expected quality and quantity of work, required travel (if any), external market and internal value when determining a new employee's salary level. Salaries will differ based on these factors, the position's level and expected contribution, and the employee's benefits elections. Offers will typically be in the bottom half of the range.
- We anticipate the salary range to be $113,480.25 - $155,000.00 per year. The upper end of this range is not likely to be offered, as an individual's compensation can vary based on several factors. These factors include, but are not limited to, geographic location, experience, training, education, and local market conditions. Eligible employees may receive a bonus. Stride offers a robust benefits package for eligible employees that can include health benefits, retirement contributions, and paid time off.
The above job is not intended to be an all-inclusive list of duties and standards of the position. Incumbents will follow any other instructions, and perform any other related duties, as assigned by their supervisor. All employment is "at-will" as governed by the law of the state where the employee works. It is further understood that the "at-will" nature of employment is one aspect of employment that cannot be changed except in writing and signed by an authorized officer.
Stride, Inc. is a Federal Contractor, an Equal Opportunity/Affirmative Action Employer and a Drug-Free Workplace. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, age, disability, protected Veteran status age, or genetics, or any other characteristic protected by law.
Job Type
Regular
Regular
The above job is not intended to be an all-inclusive list of duties and standards of the position. Incumbents will follow any other instructions, and perform any other related duties, as assigned by their supervisor. All employment is "at-will" as governed by the law of the state where the employee works. It is further understood that the "at-will" nature of employment is one aspect of employment that cannot be changed except in writing and signed by an authorized officer.
If you are a job seeker with a disability and require a reasonable accommodation to apply for one of our jobs, you can request the appropriate accommodation by contacting stridecareers@k12.com.
Equal Opportunity Employer/Protected Veterans/Individuals with Disabilities
Stride, Inc. is an equal opportunity employer. Applicants receive consideration for employment based on merit without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or protected veteran status, or any other basis prohibited by federal, state, or local law. Stride, Inc. complies with all legally required affirmative action obligations. Applicants will not be discriminated against because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant.
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