Sr. RFP and Proposal Writer (Remote)

Join Us!
Take the next step in your journey at Inspira Financial. You will help businesses and individuals thrive today, tomorrow, and into retirement. Become part of a company that is people centric and client obsessed in every interaction; a community of forward-thinking individuals focused on driving results to deliver our mission with an unwavering commitment to integrity. Join us as we strengthen and simplify the health and wealth journey -- relentlessly pursuing better outcomes for all. We believe in finding the best talent! While some roles are based at one of our office locations, remote roles can sit in any of the following states: AL, AZ, FL, GA, IA, IL, IN, MI, MN, MO, NC, NE, PA, SC, TN, TX, UT, VA and WV. Remote status and role locations are subject to change. Relocation is not provided.
Employees within a 90-minute radius of our Oak Brook, IL headquarters are required to adhere to the company in-office work guidelines of 4 days per month minimum from 10 am to 2 pm (1 of the 4 days must be a Monday or Friday).
This requirement does not apply to support specialist positions.
Don't meet every single requirement? Here at Inspira Financial, we believe there is no "perfect" candidate and want to encourage applying even if all the requirements listed aren't met. Our goal is to build an authentic workplace by valuing diversity in our candidates. We work to ensure that our team reflects the diversity of the businesses and clients we serve. We are always looking to expand our growing team with dynamic and enthusiastic individuals. If you enjoy a collaborative, fun environment that champions career development, Inspira Financial is the place for you! We look forward to receiving your application! Check out this Inspira Financial video to learn more about our company!
Inspira Financial provides health, wealth, retirement, and benefits solutions that strengthen and simplify the health and wealth journey. With more than 7 million clients, representing over $62 billion in assets, Inspira works with thousands of employers, plan sponsors, recordkeepers, TPAs, and other institutional partners -- helping the people they care about plan, save, and invest for a brighter future. Inspira relentlessly pursues better outcomes for all with our automatic rollover services, health savings accounts, emergency savings funds, custody services, and more. Learn more at inspirafinancial.com .
We have been recognized for our remarkable growth on lists such as Crain's Fast 50 and Inc. 5000, and for our outstanding workplace culture and benefits with Built In's 2025 Best Places to Work and Gallagher's 2022 Best-In-Class Employer awards.
Job Summary & Responsibilities
The Sr. RFP and Proposal Writer will report to the Sr. Manager, Sales Operations in Health & Benefits Sales. This role provides advanced support to our sales and client management teams by driving initiatives aligned with enterprise goals while ensuring a consistent, collaborative and positive overall experience. The Sr. RFP and Proposal Writer is accountable for managing the request for proposal (RFP) process on high-profile, complex opportunities through cross-functional collaboration. Additional responsibilities include, but are not limited to: completing request for quote (RFQ), request for information (RFI), identifying gaps in information, resolving proposal-related issues through research in collaboration with business partners, and managing follow-up requests. Success in this role demands exceptional multitasking abilities, the ability to consistently meet or exceed deadlines, and a commitment to delivering excellence in a fast-paced, dynamic setting.
Additional project work to support the overall sales organization and its members will be required, as needed. This additional work may include product and process training, Salesforce entry and reporting assistance, leading advanced opportunity meetings, and handling internal and external deadline escalations.

• Own the end-to-end management of assigned RFPs, ensuring accountability throughout the process, meeting deadlines 100% of the time
• Provide advanced support to sales and client management teams on high-profile, complex opportunities, with a focus on winning new business and client retention
• Manage high-volume and deliver high-value RFP support ensuring Inspira becomes an RFP finalist
• Effectively manage job responsibilities in a dynamic work environment as both an individual and team contributor
• Cultivate and maintain relationships across the enterprise
• Use various templates to produce standardized documents (pricing proposals, questionnaire responses)
• Collaborate with internal SMEs and business partners in product development, legal, IT security, implementation and client management
• Effectively use technologies such as Salesforce and Loopio
• Ensure all RFP responses follow brand, style, and tone guidelines
• Review and edit responses provided by SMEs and business partners as necessary
• Ensure responses effectively address key requirements, hot buttons, and established win theme
• Proactively seeks opportunities to share expertise, lessons learned, and best practices to support team development and collaboration
• Assist in maintenance of Loopio content library as the source of truth for RFP/RFI question/answer sets
• Support proposal content management by identifying and sharing new content for potential inclusion in the Loopio content library
• Motivated to discover ways to optimize workflows
• Support and mentor other colleagues with various facets of the job tasks and skillsets
• Additional project work to support the overall sales organization. Work may include: product and process training, leading advanced opportunity meetings, and handling internal and external and deadline escalations.
• Actively participate in weekly and monthly team meetings
• Support other team initiatives and processes as directed which may include advanced knowledge of responsibilities and needs of sales and client management teams

Preferred Qualifications
Education & Experience:

• Bachelor's Degree in business, health care, or a related field
• 3-5 three years managing proposals
• Experience with federal, state, or labor group RFPs (bonus)

Skills & Abilities:

• Advanced knowledge of internal systems, organizational structure and appropriate enterprise contacts required to carry out job functions
• Exceptional understanding of products, and enterprise and team processes
• Advanced organizational skills with strong attention to detail and drive to adhere to challenging deadlines
• Ability to prioritize multiple projects running concurrently with overlapping deadlines
• Strong aptitude for prioritization and multitasking, with the ability to effectively manage changing priorities
• A drive to learn and apply new concepts quickly
• Foster strong relationships with internal subject matter experts with particular attention to developing product knowledge
• An affinity for accuracy and efficiency
• Ability to maintain sound judgement, critical thinking skills and maintain professionalism under pressure
• Proficient with Adobe and Microsoft applications (Outlook, Excel, Word, PowerPoint)
• Advanced verbal and written communication skills, including grammar proficiency
• Must write and review for accuracy, grammar, readability, style, terminology and more.
• Experience with Loopio and Salesforce CRM preferred

Other Requirements:

• Infrequent travel
• Ability to work overtime
• Prolonged periods of sitting at a desk and working on a computer

Compensation & Benefits
$70,000-$80,000 per year