Sr. Proposal Lead

Rightway•Miami, FL

4h•$100,000 - $118,000

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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.

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