People Matter

Sr. RFP Proposal Lead



New York, NY, USA · Remote
Posted on Wednesday, April 10, 2024


The Sr. Proposal Lead will prepare high-quality, strategic client-focused questionnaires in compliance with prospect instructions and deadlines, sales strategies, and business needs. You will collaborate with Subject Matter Experts (SMEs) to ensure accurate answers and use SME feedback to respond in a unified voice to our most complicated bids. You will partner with the Director of Proposal Responses on improved process changes and a library content overhaul. The Sr. Proposal Lead should be a detail-oriented team player who possesses strong organizational and decision-making skills. Strong interpersonal skills are essential.


  • Proposal Writing

    • Collaborate with sales, marketing, and subject matter experts to develop winning proposal strategies for key prospects.
    • Analyze RFP/RFQ requirements and develop a clear understanding of client needs and evaluation criteria.
    • Format proposals, gather assets, and write and edit responses for RFPs, RFIs, and prospect questions to support the Commercial Sales Team and other internal clients.
    • Utilize cloud-based proposal automation software to complete RFPs (Responsive).
    • Ensure draft responses to RFPs, RFIs, and prospect questions are compliant and professionally produced within customer-defined requirements and timeframes.
    • Manage each RFP/RFI/Proposal project from start to finish, ensuring all internal and external deadlines are met.
    • Develop executive summaries, cover letters, and other sections to effectively communicate key messages and value propositions.
    • Craft a standardized response booklet to leverage for certain qualified opportunities.
    • Collaborate with other proposal team members as needed during proposal development initiatives.

    Proposal Process Maintenance

    • Help identify opportunities to streamline and improve the proposal development process including best practices, tools, and templates to enhance efficiency and effectiveness.
    • Assist in maintaining our cloud-based proposal automation software by working closely with internal SMEs and staying informed of changing messaging, new product launches, company policies, and content.
    • Work with the proposal team to run regular duplicate reports and maintain tagging, collections, and sectioning systems within the Responsive library.
    • Ensure RFPs, RFIs, and proposals are stored and filed in our Google Drive.


  • Must be an experienced proposal writer for care navigation or PBM solution
  • Bachelor’s Degree
  • Minimum five years of relevant work experience in a highly regulated business climate with proposal management, project management, and analytical skills
  • An exceptional writer who succinctly delivers a punch with prose
  • Technically savvy (Google Workspace, Responsive, Salesforce, etc.)
  • Strategic thinker with excellent prioritization and time management skills
  • Demonstrated professionalism and flexibility required to interact independently with the diverse and growing internal and external customer base
  • Ability to work independently with minimal guidance
  • Exceptional time management skills


  • Knowledge of AP style guidelines
  • Professional certifications such as APMP (Association of Proposal Management Professionals).

SALARY: $100,000-$115,000


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.