Head of Program 467 views2 applications

The Head of Program is a full-time position that works directly with our Founder + CEO to strategically oversee the development and success of the Oyster Sunday (OS) Benefits platform and its partnerships. The Head of Program will develop strategy-driven objectives and manage the OS Benefits Team to ensure that the program is developed effectively and innovatively. This is a remote, full-time position.


  • Plan and direct the overall strategic design, implementation, growth, communication, and administration of OS Benefits to establish competitive and cost-effective benefits offerings.
  • Lead a roadmap of data-driven goals to drive conversion improvement using web analytics, channel performance data, and internal financial data.
  • Collaborate with the Founder + CEO to identify an annual budget for the program and develop a sponsorship model for corporate engagement, partnerships, and sponsorships.
  • Identify, develop, and lead all corporate sponsorship and new business opportunities for OS Benefits that are reflective of program objectives and core values.
  • Develop and implement strategies that expand the reach and effectiveness of the program to existing and potential customers.
  • Devise and implement evaluation strategies to monitor performance and analyze the program’s competitive market position.
  • Manage a team of direct reports to provide feedback and resolve complex problems; is a leader in OS Benefit’s company culture and development.
  • Research, interpret, and present analyses of industry benchmarking to ensure the program is exceeding the expectations of our competitors, adjusting for gaps in service to retain and attract user engagement.
  • Initiate and set strategic objectives for OS Benefits; work with the team to identify quarterly goals.
  • Monitor trends and best practices in the employee benefits industry and make recommendations for improvement.
  • Attend and represent OS Benefits at industry events, panels, and conferences to increase brand awareness and potential partnership opportunities.
  • Foster and work to maintain an entrepreneurial growth culture throughout the OS Benefits team.
  • Ensure the program operations and development adhere to legal regulations and internal policies.
  • Support other OS Benefits projects as needed.

Skills & Qualifications:

  • Minimum 5-7 years’ experience in program development position with a strong leadership background.
  • Preferred experience of working within the hospitality sector, employee benefits, or human resources industry.
  • Thorough understanding of project/program management techniques and methods.
  • Ability to effectively and swiftly build relationships to establish trust and confidence.
  • Exceptional communication skills, highly organized, collaborative, and detail oriented.
  • Empathetic, positive attitude with a desire to help our customers.
  • Experience leading and managing projects from concept to completion.
  • Solutions-oriented and displays innovation and initiative.
  • Self-motivated, able to prioritize, and can work independently as well as on a team.

Salary: $100,000 – 115,000 annually, including benefits

Hours: 40 hours per week

  • May include extra hours and working weekends, events, additional hours, or holidays as needed
  • General hours Monday-Friday 9am-6pm, remote


Oyster Sunday Benefits is a platform that provides users access to a robust offering of services that fits both their budgets and the everyday needs of their teams. From preventative care to continuing education, family planning and even mental health, we believe this shared investment can help dignify and legitimize hospitality + independent contractor work as a sustainable, long-term profession.


Oyster Sunday provides equal employment opportunity to all persons regardless of age, color, national origin, citizenship status, physical or mental disability, race, religion, creed, gender, sex, sexual orientation, gender identity and/or expression, genetic information, marital status, status with regard to public assistance, veteran status, or any other characteristic protected by federal, state or local laws.

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OS Benefits is a technology solution that connects independent operators and their teams to affordably priced preventative care, crisis insurance, lifestyle services and career resources at the reduced market cost to fit the needs of their lives.
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