Full-Time

Benefits Director

Updated on 7/21/2026

Stride

Stride

5,001-10,000 employees

Online and blended education solutions provider

No salary listed

Remote in USA

Remote

Remote within the United States.

Category
People & HR (1)
Required Skills
Workday HRIS
Visio
Word/Pages/Docs
Human Resources Information System (HRIS)
Oracle
Excel/Numbers/Sheets
PowerPoint/Keynote/Slides

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Requirements
  • 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
Responsibilities
  • 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.
Desired Qualifications
  • Bachelor’s Degree in human resources or related field
  • Attainment or pursuit of Certified Employee Benefit Specialist (CEBS)

Stride offers online and blended education solutions for learners of all ages, providing full-time online schools, career-focused programs, and corporate training. Its products work by delivering personalized learning through technology-enabled teaching, with online curricula and blended formats that serve K-12 students, adult learners, and corporate clients. Revenue comes from tuition, state funding for public school partnerships, and corporate training programs. Stride differentiates itself through a clear emphasis on career readiness and personalized learning, a broad mix of learners, and a commitment to social responsibility and inclusivity integrated into curriculum design and operations. The company's goal is to help learners reach their full potential by expanding access to online and blended education and focusing on career learning.

Company Size

5,001-10,000

Company Stage

IPO

Headquarters

Herndon, Virginia

Founded

1999

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Simplify Jobs

Simplify's Take

What believers are saying

  • Career Learning revenue grew 16% in Q3, offsetting a 3.6% decline in General Education.
  • Free cash flow margin expanded 5 percentage points to 13.6% over the trailing 12 months.
  • Stock surged 161% over five years, outpacing the S&P 500's 77.6% return since July 2021.

What critics are saying

  • A class action lawsuit alleging securities fraud over ghost students has a 60–80% probability in 6–12 months.
  • Platform migration failures drove loss of 10,000–15,000 enrollments, causing a 50% stock plunge and institutional exits.
  • State funding volatility threatens over 40% of revenue due to public school partnership budget instability.

What makes Stride unique

  • Stride School of Business is India's first AI-native BBA program with AI embedded across all subjects.
  • Every student receives an Apple MacBook and accesses 15+ AI tools like Claude and ChatGPT from day one.
  • The program admits only the top 20% of applicants via the Stride Business Aptitude Test with scholarships up to 100%.

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Benefits

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Stride, Inc.
Jun 19th, 2026
75 top companies with remote jobs this summer.

75 top companies with remote jobs this summer. Stride was recognized by FlexJobs as one of the top 75 companies hiring for remote roles in 2026, highlighting the company's continued commitment to flexible work opportunities. Featured alongside leading employers across healthcare, technology, and government, the recognition reinforces Stride's position as an employer of choice for professionals seeking remote careers in a competitive job market.

Yahoo Finance
Mar 16th, 2026
Stride and IMAX beat BrightView as cash-producing stocks for long-term investors

Two stocks with strong cash flow stand out as long-term holdings, whilst one faces challenges, according to StockStory analysis. BrightView, a landscaping services company, is flagged as risky. Sales have declined 1.8% annually over two years, whilst earnings per share contracted 3.3% annually over five years. The company shows low returns on capital, indicating poor fund allocation. Stride, an education technology firm, demonstrates strong fundamentals with 14.6% annual revenue growth over five years and 45% annual earnings per share growth over two years. Trading at 9.8x forward price-to-earnings, the stock appears attractively valued. IMAX shows exceptional performance with 24.5% annual revenue growth over five years and a 20.8% free cash flow margin. Its returns on capital are improving as historical investments mature.

Yahoo Finance
Mar 14th, 2026
Kadensa Capital dumps entire Stride stake worth $23M after stock plunges 50%

Kadensa Capital liquidated its entire position in Stride during the fourth quarter, selling 157,101 shares with an estimated transaction value of $23.40 million, according to a 17 February SEC filing. The education technology company's shares have fallen 29.1% over the past year to $84.78 as of 12 March, underperforming the S&P 500 by 50 percentage points. The decline followed a significant earnings miss in October after a faulty platform upgrade caused Stride to lose between 10,000 and 15,000 new enrollments from its total base of less than 250,000 students. Stride provides online curriculum and educational services for K-12 and adult learners, generating $2.52 billion in trailing twelve-month revenue. The company has a market capitalisation of $3.59 billion.

Yahoo Finance
Mar 7th, 2026
Divisadero Street Capital dumps $55.9M Stride stake amid 39% share price decline

Divisadero Street Capital Management sold its entire stake in Stride, exiting 375,000 shares during the fourth quarter of 2025, according to a February SEC filing. The position was previously valued at $55.9 million, representing approximately 2.4% of the firm's assets. As of 13 February 2026, Stride shares traded at $84.89, down 39.1% over the past year, trailing the S&P 500 by 50.8 percentage points. The education technology company, which delivers online curriculum and educational services to K-12 and adult learners, has a market capitalisation of $3.6 billion. Divisadero had only initiated its position in Stride during the third quarter before completely exiting. The firm's top holdings now include SGHC at $140.3 million and INDV at $99.9 million.

Yahoo Finance
Mar 1st, 2026
South Street Advisors offloads $2.5M stake as Stride shares halve in value

South Street Advisors sold 27,651 shares of Stride during the fourth quarter, worth approximately $2.51 million, according to a Securities and Exchange Commission filing dated 9 February 2026. The online education company's stock has fallen 38.32% over the past year. Following the sale, Stride represents 0.51% of South Street Advisors' $712.19 million portfolio. The firm's quarter-end position value in Stride declined by $8.80 million due to both share sales and market price movements. Stride, which provides technology-based education services for K-12 and adult learners, has struggled since implementing a platform upgrade last summer. Management estimates the disruption may have cost between 10,000 and 15,000 enrolments from its roughly 257,000 student base. Despite recent challenges, Stride shares have delivered eight times returns over the past decade.