Director, Benefits at Pocket Outdoor Media

| Greater Boulder Area | Remote
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 We are looking for a leader who is curious, loves to solve complex problems in fast-paced and ambiguous environments, and is passionate about being an employee advocate to join our growing team. The Director of Benefits will be responsible for oversight for design, compliance, administration, and communications for health, welfare & retirement plans in the United States and Canada. We’re looking for someone in this role who is energized by delivering a great employee experience, from the first date of enrollment and each day thereafter. This person will be energized by the prospect of being both hands-on and strategic, and by the chance to directly influence the way we think about our benefits programs. These responsibilities would grow to include global compensation strategy & governance. This role is an integral part of the People Operations Team, reporting directly to the Chief People Officer.


  • Plans and directs the implementation and administration of benefits programs designed to ensure employees against loss of income due to illness, injury, or retirement.
  • Plans the modification of existing benefits programs.
  • Develop & execute strategy by closely partnering with the Leadership Team and Finance.
  • 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.
  • Prepares and monitors People Operations departmental budget.

Experience & Skills

  • 10+ years experience in HR, including 5+ years of benefits experience
  • 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
  • Strong leadership and team management skills.
  • Like to solve multiple complex problems with and without others, sometimes happening concurrently 
  • Strong business acumen, particularly financial and analytical skills
  • Knowledge of all federal, state and local regulations and compliance requirements related to employee benefits
  • Strong analytical skills and ability to interpret and communicate data.
  • High proficiency with Microsoft Excel/Google Sheets
  • 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 

Nice-To-Have Experience

  • Compensation experience is a plus
  • Global benefits experience preferred
  • Professional development experience is a plus


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

All qualified applicants will receive consideration for employment without regard to race, color, religion, gender, sexual identity, national origin, protected veteran status, or disability status. Any offer of employment is contingent upon the results of a pre-employment reference check. 

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