This is a very exciting and highly innovative time here at Outside.

Champion Employee Happiness and Health

Outside Interactive, Inc., the premier hub for active lifestyle enthusiasts, offers best-in-class content and experiences to more than 70 million of the world’s most passionate outdoor, wellness, and endurance enthusiasts every month. We inspire a broad and diverse audience to do the activities they love with greater enjoyment, inspiration, and knowledge and are dedicated to making real change in the outdoor and fitness industries

We are looking for a visionary leader who is passionate about transforming the employee experience and thrives in dynamic, ever-evolving environments. As our Director of 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. This role is all about making our employees feel supported, valued, and appreciated from day one.

Imagine having the power to influence the resources and strategies that create the best career experience for every employee at Outside. 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.

At Outside, we’re all about innovation and being on the cutting edge to build the best culture possible. You’ll be right in the middle of this mission, helping us stay ahead in employee satisfaction and engagement. Plus, you get to work for a company whose mission is to get everyone outside—how awesome is that?

Reporting directly to the Chief People Officer, you’ll be a vital part of the People Operations Team, championing our employees at every level. Join us in making Outside an incredible place to work, where employees’ voices are heard, their well-being is our top priority, and every day brings new opportunities to connect with the great outdoors.

This role is preferably to reside in the Denver/Boulder area; but can also be remote in the United States and Canada


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

  • Conduct periodic reviews and analyses of existing benefits plans, policies, and procedures, and plans the modification of existing benefits programs.
  • Develop & execute strategy by closely partnering with the Leadership Team and Finance
  • Oversee annual benefits renewal process. Analyze proposals, negotiate rates/fees, and make recommendations to leadership
  • Develop and oversee processes for benefits administration including enrollment, changes, terminations, and resolving issues
  • Understands external benchmarking & trends to evaluate and deliver a competitive benefit program
  • Design & innovate while managing for efficiency in health & welfare, disability, and PTO programs
  • Builds 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 benefit loss and claims control, budgets, and special projects
  • Develop and execute 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
  • Leverage 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.
  • Keep current on benefits regulations, legislation, trends, and best practices

Experience & Skills:

  • 10+ years of experience in Human Resources, including 10+ years specializing in benefits management (401k, health and welfare plans, HRIS, etc)
  • Extensive knowledge of 401k plans and plan administration
  • 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 financial and analytical skills
  • 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, i.e pivot tables and vlookups

Nice to Have(s):

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


  • Bachelor's degree is required. Master's preferred.
  • Course work in business administration or related fields is preferred.
  • Appropriate level of work experience may be substituted for educational requirements.

For jobs performed in Boulder, Colorado: Employees can expect to be paid a salary between $140,000 to $180,000. Other benefits include health care, vision, dental, retirement, Flexible Time Away, sick leave, and many more. The salary range displayed is specifically for those potential hires who will work or reside in the state of Colorado if selected for this role, and may vary based on market data/ranges, an applicant’s skills and prior relevant experience, certain degrees and certifications, and other relevant factors

We are committed to fostering a diverse and inclusive workplace. Outside Inc is an Equal Opportunity Employer. We do not discriminate based on race, color, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other legally protected characteristics. Pursuant to applicable laws, we also make accommodations for qualified individuals with disabilities. We believe a diverse team is a strong team, and we encourage candidates from all backgrounds to apply.