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**Experienced Global Benefits Director – Strategic Benefits Management and Employee Experience Expert**

Remote, USA Full-time Posted 2025-11-03

About Us

Outside Interactive, Inc. is a leading hub for active lifestyle enthusiasts, offering best-in-class content and experiences to over 70 million passionate outdoor, wellness, and endurance enthusiasts every month. Our mission is to inspire a broad and diverse audience to do the activities they love with greater enjoyment, inspiration, and knowledge, while making real change in the outdoor and fitness industries.

Join Our Team

We're seeking a visionary leader who is passionate about transforming the employee experience and thrives in dynamic, ever-evolving environments. As our Director of Global Benefits, you'll be at the heart of shaping and revolutionizing our benefits programs, making a real impact on health, welfare, and retirement plans across the U.S. and Canada.

About the Role

This is a unique opportunity to join a dynamic team and make a significant impact on the employee experience. As our Global Benefits Director, you'll lead innovative benefits initiatives, working closely with the executive team to keep our offerings fresh, exciting, and employee-focused. Your hands-on approach will constantly improve how we manage and think about benefits, making you a key player in our mission to create an amazing workplace culture.

Responsibilities

  • Plans and directs the implementation and administration of benefits programs designed to attract, retain, and motivate employees, while ensuring employees against loss of income due to illness, injury, or retirement.
  • Conducts periodic reviews and analyses of existing benefits plans, policies, and procedures, and plans the modification of existing benefits programs.
  • Develops and executes strategy by closely partnering with the Leadership Team and Finance.
  • Oversees annual benefits renewal process. Analyzes proposals, negotiates rates/fees, and makes recommendations to leadership.
  • Develops and oversees processes for benefits administration, including enrollment, changes, terminations, and resolving issues.
  • Understands external benchmarking & trends to evaluate and deliver a competitive benefits program.
  • Designs and innovates while managing for efficiency in health & welfare, disability, and PTO programs.
  • Builts and values internal/external partnerships to get the job done.
  • Prepares written, verbal, and training information to inform employees of benefits programs options within insurance plans, 401(k), life, and special employer-sponsored plans.
  • Ensures compliance with all business and legal plan requirements, directs preparation and filing of legally required reports and documents.
  • Advises, consults, and serves as a member of the People Operations Team in the development and execution of short-term and long-range plans and budgets based on broad corporate goals, acquisitions, strategic planning, and growth objectives.
  • Evaluates and analyzes the results of the programs and services regularly and systematically; reports these results to the CPO, CFO, and CEO in addition to other management reporting such as benefits loss and claims control, budgets, and special projects.
  • Develops and executes innovative marketing campaigns and communication strategies that make our benefits programs transparent and understandable for all employees, ensuring they are fully informed and can make the best choices for their personal and family needs.
  • Leverages artificial intelligence to streamline benefits administration processes, enhance decision-making, and personalize employee experiences, ensuring our programs are not only efficient but also ahead of the technological curve.
  • Monitors HRIS system and EDI integrations for accuracy in employee enrollments.
  • Keeps current on benefits regulations, legislation, trends, and best practices.

Experience and Skills

We're looking for a seasoned benefits professional with a strong track record in benefits management, including 401(k) plan design, administration, and compliance, as well as global benefits programs, with a strong focus on Canada's benefits landscape.

  • 10+ years specializing in benefits management (401k, health and welfare plans, HRIS, etc.). Director-level experience preferred.
  • In-depth expertise in 401(k) plan design, administration, and compliance, including fiduciary responsibilities and regulatory requirements.
  • Comprehensive experience in managing global benefits programs, with a strong focus on Canada's benefits landscape, including health, retirement, and statutory plans.
  • Proven track record in managing benefits integration during mergers and acquisitions, including due diligence, plan harmonization, and change management.
  • Strong analytical skills and ability to interpret and communicate data.
  • Familiarity with current tools for the workplace, including chat GPT.
  • High proficiency with Microsoft Excel/Google Sheets, including pivot tables and vlookups.
  • Experience working with external vendors/brokers who provide co-sourced or outsourced benefits administration services.
  • Thorough knowledge of ERISA and other laws governing employee and retirement benefits; strong understanding of PPACA and experience with state and local mandates.
  • Knowledge of all federal, state, and local regulations and compliance requirements related to employee benefits.
  • Strong leadership and team management skills.
  • Ability to communicate clearly and appropriately to the audience in front of you, whether it's a consultative style, executive presence, or down to the details, or to one person, or a big room.
  • Like to solve multiple complex problems with and without others, sometimes happening concurrently.
  • Strong business acumen, particularly strong financial and analytical skills.

Nice to Have(s)

  • Compensation experience is a plus.
  • Global benefits experience, especially Canada, preferred.
  • Professional development experience is a plus.

Education

We're looking for a candidate with a Bachelor's degree in business administration or a related field, with a Master's degree preferred.

Location

This role is preferably located in the Denver/Boulder area, but can also be remote in the United States and Canada.

Compensation and Benefits

We offer a competitive compensation package, with a salary range of $140,000 to $180,000, depending on experience and qualifications. Other benefits include health care, vision, dental, retirement, Flexible Time Away, sick leave, and many more.

Why Join Us?

We're committed to fostering a diverse and inclusive workplace, and we believe a diverse team is a strong team. We encourage candidates from all backgrounds to apply.

How to Apply

If this role sounds like a perfect fit, don't hesitate. Apply today and let's build the future together.

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