Proposal Specialist

At HSA Bank, we’re working toward a world where everyone is empowered to save for a healthy future. Our offerings in the healthcare savings space drive down healthcare costs, increase access, and assist with decision-making for consumers, health plans, partners, and advisors. Are you ready to join us? As part of the Growth Operations Team, the Proposal Team partners with Sales, Relationship Management, Business Development, Consultant Relations, the Strategic Partnership Group, and subject matter experts across the organization to deliver accurate, high-quality, and timely responses to HSA Bank’s RFPs and RFIs in a fast-paced, deadline-driven environment. The Proposal Specialist plays a critical role in managing multiple concurrent proposals at varying stages of completion, ensuring that each submission is complete, compliant, and tailored to client requirements. Primary responsibilities include evaluating RFP/RFI requirements; leading kick-off and strategy calls with business partners; developing and actively managing detailed project timelines; coordinating and synthesizing input from multiple internal stakeholders; and drafting, editing, and refining responses with a high degree of accuracy and consistency. The role also requires securing necessary approvals, tracking progress against deadlines, and packaging final deliverables for submission. This position demands exceptional organizational skills, prioritization, and the ability to seamlessly shift between competing priorities without compromising quality. A strong focus on detail-oriented review, version control, and adherence to requirements is essential to ensure proposals meet all client specifications and internal standards. In addition to core responsibilities, the Proposal Specialist will support ad hoc projects and initiatives as needed, often requiring rapid turnaround and adaptability. The team reports up through the Chief Revenue Officer and are recognized for their collaborative approach and reputation for delivering high-quality work. The ideal candidate thrives in a deadline-driven environment, demonstrates excellent multi-tasking abilities, maintains rigorous attention to detail, and effectively collaborates with individuals across diverse communication styles and functions. What you will do Thoroughly reads and evaluates assigned RFP/RFI submission requirements and due dates. Conducts kick-off/strategy calls with business partners for assigned high-profile RFPs/RFIs. Prepares, communicates, and manages project timelines for assigned RFPs/RFIs. Build responses for a wide range of questionnaires utilizing a database of questions and responses. Utilizes approved templates while following brand style guidelines. Obtains and retains approvals and final proposals. Package and deliver proposals for e-delivery or hard copy, as requested. Track and communicate proposal progress in Salesforce and during weekly status meetings. Ad hoc requests and assignments, such as reporting, quality control projects, template redesign, etc. Involved in strategy discussions to find opportunities for efficiencies or ways to elevate output. Other tasks, as assigned. Skills and Abilities Literate in all Microsoft products Superior organizational, problem-solving and attention-to-detail skills Strong interpersonal skills with colleagues at every level of the organization Excellent proofreading and writing skills BS degree in business-related field preferred. Proposal/RFP/RFI experience preferred. Salesforce experience preferred. Accurate and organized in presentation of materials and dissemination of information in communicating information to external and internal customers. Highly capable of managing tasks independently and collaborating with team members to achieve shared goals. Excellent interpersonal skills to work effectively as a member of a fast-paced team. Confident with working with individuals from all levels of the organization, including at the Executive and C-Suite levels. Self-directed motivation, innovation and accuracy within tasks assigned. Education Qualifications H.S. Diploma or General Education Degree (GED) required Candidates with advanced degrees (Associates, Bachelor's, and/or Master's) preferred Candidates with some combination of coursework and experience, or extensive related professional experience, are eligible for consideration. Experience Qualifications 3-4 years of business experience Proposal experience preferred The estimated salary range for this position is $70,000USD to $80,000USD. Actual salary may vary up or down depending on job-related factors which may include knowledge, skills, experience, and location. In addition, this position is eligible for incentive compensation. LI-EF1 Webster Financial Corporation and its subsidiaries (“Webster”) are equal opportunity employers that are committed to sustaining an inclusive environment. All qualified applicants will receive consideration for employment without regard to race, color, religion, age, marital status, national origin, ancestry, citizenship, sex, sexual orientation, gender identity and/or expression, physical or mental disability, protected veteran status, or any other characteristic protected by law. We partner with our clients to help them achieve meaningful health and wealth outcomes through and beyond lifecycle with personalized, data-rich digital experiences. We help over 3 million individuals and 30,000 employers of all-sized companies, nationwide, maximize their employee benefits. And we work with approximately 6,500 agents, brokers and consultants who serve employers. We continue to challenge the status quo and harness innovation to create value for our customers and clients. We constantly develop new products and services to ensure we meet and exceed evolving health and wealth needs. Not finding the right fit? Let us know you're interested in a future opportunity by clicking Get Started below or create an account by clicking 'Sign In' at the top of the page to set up email alerts as new job postings become available that meet your interest!