Director, Proposal Development & Underwriting

The Director of Proposal Development & Underwriting is a strategic leader responsible for managing the development of winning PBM proposals while also overseeing the underwriting process that supports competitive, risk-adjusted pricing strategies. This dual-role position ensures that proposals are not only responsive and compelling but also financially sound and aligned with the organization’s revenue and margin goals. This leader collaborates across departments to drive growth through high-quality RFP responses, strategic deal structuring, and risk-based pricing models.

The essential functions include, but are not limited to the following:

• Lead a high-performing team of proposal managers, writers, and coordinators.
• Oversee customized, compliant, and compelling responses to RFPs, RFIs, and procurement opportunities.
• Align proposal strategy with sales goals, market positioning, and client-specific needs.
• Manage proposal schedules, kickoff meetings, response workflows, and content libraries.
• Oversee underwriting of PBM deals.
• Collaborate with Finance, Clinical, and Sales teams on risk evaluation, pricing integrity, and client profitability.
• Provide final review and sign-off on underwriting recommendations in RFP responses.
• Integrate underwriting insights into compelling proposal narratives.
• Work closely with Sales, Finance, Legal, Clinical, and Operations to ensure aligned proposal and pricing deliverables.
• Advise Sales leadership strategically on deal structure, contract terms, and risk tolerance.
• Partner with subject matter experts to refine reusable content.
• Ensure proposals meet formatting, accuracy, and compliance standards.
• Maintain documentation for underwriting and pricing assumptions.
• Track and analyze win/loss metrics, pricing competitiveness, and underwriting accuracy for continuous improvement.

Other job duties include, but are not limited to the following:

• Bachelor’s degree required; degree in Finance, Business, Healthcare Administration, or related field preferred.
• 8+ years of experience in healthcare, PBM, or health plan industry with a focus on proposals and underwriting.
• Minimum 3 years in a leadership role managing both proposal and pricing/underwriting functions.
• Deep understanding of PBM pricing strategies, plan design, rebate structures, and risk modeling.
• Strong project management skills with the ability to manage multiple complex proposals simultaneously.
• Proficiency in Microsoft Office, proposal software (e.g., Loopio, RFPIO/Responsive), and financial modeling tools.

Preferred Attributes

• Strategic thinker with strong business acumen and attention to detail.
• Confident communicator with the ability to influence senior leaders and cross-functional teams.
• Experience in value-based contract structures or alternate funding models is a plus.
• Thrives in a fast-paced, deadline-driven environment with high growth potential.

Supervisory Responsibilities

Manages the work of other managers and individual contributors.

Work Environment

The noise level in the work environment is usually low to moderate.

Physical Demands

The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this position. Reasonable accommodations may be made to enable individuals with disabilities to perform the functions. While performing the duties of this position, the employee is regularly required to talk or hear. The employee frequently is required to use hands or fingers, handle or feel objects, tools, or controls. The employee is occasionally required to stand; walk; sit; and reach with hands and arms. The employee must occasionally lift and/or move up to 25 pounds. Specific vision abilities required by this position include close vision, distance vision, and the ability to adjust focus.

Travel Requirements

Up to 15% travel may be required.

This job description in no way states or implies that these are the only duties to be performed by the employee(s) incumbent in this position. Employees will be required to follow any other job-related instructions and to perform any other job-related duties requested by any person authorized to give instructions or assignments. All duties and responsibilities are essential functions and requirements and are subject to possible modification to reasonably accommodate individuals with disabilities. To perform this job successfully, the incumbents will possess the skills, aptitudes, and abilities to perform each duty proficiently. Some requirements may exclude individuals who pose a direct threat or significant risk to the health or safety of themselves or others. The requirements listed in this document are the minimum levels of knowledge, skills, or abilities. This document does not create an employment contract, implied or otherwise.

The Company complies with employment regulations as they apply to the location of service.