Sr. Proposal Lead

The Senior Proposal Lead is a key player in securing business from our largest and most strategic prospects, directly contributing to Rightway’s revenue growth. In this high-impact role, you’ll own complex, high-stakes proposals end to end—shaping strategy, driving quality, and ensuring every submission reflects Rightway’s differentiated value.

Senior Proposal Leads operate within pods, serving as trusted experts within the proposal function. You’ll take primary ownership of complex bids and partner closely with Pod Leaders to provide coaching and quality oversight for Proposal Leads, helping elevate proposal standards across content, process, and execution.

As an in-house expert on Rightway’s solutions, you’ll bring deep knowledge of our products, services, and value propositions to every bid. You’ll collaborate closely with Sales and Subject Matter Experts (SMEs) to navigate complexity, refine messaging, and deliver clear, compelling, and compliant proposals that win.

WHAT YOU’LL DO:

• Own complex, high-risk proposals end to end, with full accountability for strategy, quality, and delivery.
• Analyze RFP/RFI requirements to understand client needs, evaluation criteria, and risk areas.
• Lead proposal strategy and messaging in partnership with Sales and SMEs to clearly articulate Rightway’s value and differentiation.
• Create, write, edit, and format proposal responses using cloud-based tools (Responsive).
• Drive timelines, coordinate inputs, and ensure proposals are compliant, accurate, and professionally produced.
• Partner with Pod Leaders to provide coaching and quality oversight for Proposal Leads, strengthening writing quality, structure, and overall proposal consistency across the pod.
• Drive continuous improvement within your pod, identifying and implementing enhancements to proposal content, workflows, and quality standards to improve efficiency and outcomes.

WHO YOU ARE:

• An experienced proposal professional with deep PBM proposal expertise
• Bachelor’s degree required
• 5+ years of experience in proposal and project management within a highly regulated environment
• A sharp, persuasive writer who delivers clarity and impact
• Technically proficient (Google Workspace, Responsive, Salesforce, and similar tools)
• A strategic thinker who balances speed, quality, and risk
• Comfortable owning complex work independently while coaching and supporting peers
• Highly organized, adaptable, and confident managing competing priorities
• A collaborative partner who elevates both the work and the team around them

EXTRA CREDIT: 

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

SALARY:  $100,000-118,000

Offer amounts for both remote and in office roles are influenced by geographic location.

CYBERSECURITY AWARENESS NOTICE

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 @rightwayhealthcare.com email domain. We will never ask for bank details or deposits of any kind as a condition of employment. 

ABOUT RIGHTWAY:

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 $205mm from investors including Khosla Ventures, Thrive Capital, and Tiger Global. We’re headquartered in New York City, with satellite offices in Denver and Dallas. Our clients rely on us to transform the healthcare experience, improve outcomes for their teams, and decrease their healthcare costs.

HOW WE LIVE OUR VALUES TO OUR TEAMMATES:

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 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.