People Matter

Chief of Staff to CEO



People & HR, Operations
New York, NY, USA
Posted on Saturday, April 20, 2024


We are in search of an accomplished Chief of Staff to the CEO to join our team, reporting directly to the CEO. As a proactive leader, you will instill structure and accountability in our rapidly evolving organization. Your primary mandate will be to oversee the orchestration of people and processes. Your strategic direction will be pivotal in ensuring the timely execution and successful outcomes of our initiatives, playing a critical role in our mission to revolutionize the healthcare landscape. You will serve as the key point of contact for project coordination and timelines, fostering seamless collaboration with stakeholders at all levels of the company. Moreover, your leadership will extend to identifying opportunities for operational enhancements throughout the organization, while actively driving our strategic planning endeavors.


  • Serve as the chief liaison between the CEO and various departments, ensuring seamless communication and coordination.
  • Manage the CEO's schedule and travel arrangements efficiently and effectively.
  • Prepare and review reports, presentations, and other materials for the CEO.
  • Oversee the CEO’s commercial activities, including partnerships, commercial advisors, and client relationships, to drive revenue growth.
  • Collaborate with senior leadership to develop and implement long-term strategic plans including facilitating our annual and quarterly strategic planning processes.
  • Conduct thorough research and analysis to support strategic decision-making processes.
  • Lead cross-functional teams on strategic projects, ensuring alignment with organizational objectives.
  • Develop and maintain operational processes to optimize workflow and enhance organizational efficiency.
  • Coordinate board management activities, including scheduling meetings, preparing agendas and decks, and facilitating communication between the CEO and board members.


  • You’re excited about healthcare innovation and want to make a positive impact.
  • You’re a top-notch communicator and are able to naturally connect with people in order to quickly build trust and rapport.
  • You have proven success working with all levels of management.
  • You have an ability to juggle multiple tasks at once and prioritize those with the highest impact.
  • You are able to be autonomous and agile in changing environments, with a sense of initiative and proactivity.
  • You have a proven track record in strategic planning and execution.
  • You are a student of healthcare with knowledge of healthcare regulations and industry trends.
  • You understand how to leverage data in informed decision-making.
  • You have knowledge of Microsoft Office applications such as Word and Excel; Google applications; and other project management tools.
  • You are comfortable with file management, transcription, and other administrative procedures.
  • You have 4-8 years of experience in healthcare or technology industry with at minimum a Bachelor's degree in relevant field, though bonus points for Masters (e.g., business administration, healthcare management, technology).


  • You have experience in the Navigation, PBM, and/or benefits industry.
  • You have consulting experience.
  • You have project management certifications.
  • You have data analysis skills and are able to leverage insights in your storytelling.

SALARY: $125,000.00 to $150,000.00


In response to ongoing and industry-wide fraudulent recruitment activities (i.e., job scams), Rightway wants to inform potential candidates that we will only contact them from the email domain. We will never ask for bank details or deposits of any kind as a condition of employment. If you have any questions about a suspicious interaction with Rightway, please feel free to reach out to us at


Rightway is on a mission to harmonize healthcare for everyone, everywhere. Our products guide patients to the best care and medications by inserting clinicians and pharmacists into a patient’s care journey through a modern, mobile app. Rightway is a front door to healthcare, giving patients the tools they need along with on-demand access to Rightway health guides, human experts that answer their questions and manage the frustrating parts of healthcare for them.

Since its founding in 2017, Rightway has raised over $130mm from investors including Khosla Ventures, Thrive Capital, and Tiger Global at a valuation of $1 billion. We’re headquartered in New York City, with a satellite office in Denver. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs.


We’re seeking those with passion for healthcare and relentless devotion to our goal. We need team members that embody our following core values:

1) We are human, first
Our humanity binds us together. We bring the same empathetic approach to every individual we engage with, whether it be our members, our clients, or each other. We are all worthy of respect and understanding and we engage in our interactions with care and intention. We honor our stories. We listen to—and hear—each other, we celebrate our differences and similarities, we are present for each other, and we strive for mutual understanding.

2) We redefine what is possible
We always look beyond the obstacles in front of us to imagine new solutions. We approach our work with inspiration from other industries, other leaders, and other challenges. We use ingenuity and resourcefulness when faced with tough problems.

3) We debate then commit
We believe that a spirit of open discourse is part of a healthy culture. We understand and appreciate different perspectives and we challenge our assumptions. When working toward a decision or a new solution, we actively listen to one another, approach it with a “yes, and” mentality, and assume positive intent. Once a decision is made, we align and champion it as one team.

4) We cultivate grit
Changing healthcare doesn’t happen overnight. We reflect and learn from challenges and approach the future with a determination to strive for better. In the face of daunting situations, we value persistence. We embrace failure as a stepping stone to future success. On this journey, we seek to act with guts, resilience, initiative, and tenacity.

5) We seek to delight
Healthcare is complicated and personal. We work tirelessly to meet the goals of our clients while also delivering the best experience to our members. We recognize that no matter the role or team, we each play a crucial part in our members’ care and take that responsibility seriously. When faced with an obstacle, we are kind, respectful, and solution-oriented in our approach. We hold ourselves accountable to our clients and our members’ success.

Rightway is a healthcare company looking to improve healthcare outcomes for everyone, everywhere. With that in mind, we have to consider what is good for the health of our team, the company, and the communities we operate in. As such, Rightway has determined a mandatory COVID-19 vaccination policy for all employees, in combination with other safety precautions, is the best way forward.

Rightway is PROUDLY an Equal Opportunity Employer that believes in strength in the diversity of thought processes, beliefs, background and education and fosters an inclusive culture where differences are celebrated to drive the best business decisions possible. We do not discriminate on any basis covered by appropriate law. All employment is decided on the consideration of merit, qualifications, need and performance.