Senior Proposal Manager

Want to be a bswifter? 

At bswift we’ve been transforming benefits administration since 1996, making it simpler, smarter, and more human. Our state-of-the-art, cloud-based technology and services empower employees to understand, manage, and love their benefits. From downtown Chicago, and remotely across the country, we serve thousands of companies and millions of people nationwide, reducing administrative burdens and freeing HR teams to focus on creating thriving, people-first workplaces. 

 We’re looking for motivated and goal-driven individuals who share our passion for delivering excellence and creating solutions that make a difference. The reward is a fun, flexible and creative environment with ample opportunity for professional and personal growth. If you love the bswift values of pursue excellence, embrace accountability, deliver superior service, and be a great place to work, we want to hear from you! 

The Senior Proposal Manager is an integral part of the Sales Operations team, specializing in proposal writing, project management, and content management. This role supports new business and renewal revenue by delivering high-quality responses for Benefits Administration proposals. Key responsibilities include managing RFP projects, collaborating with internal stakeholders to meet proposal requirements, maintaining the proposal database, and providing general Sales Operations support.

You will directly help develop proposal and sales enablement materials including:
• Collaborate with Sales, Operations, and Subject Matter Experts to develop proposals that meet client needs and align with our business objectives.
• Analyze RFP/RFI requirements to ensure compliance and develop proposal outlines, schedules, and content matrices.
• Conduct research and work with internal teams to gather information to support the proposal.
• Write, edit, and proofread proposal content to ensure clarity, accuracy, and consistency including executive summaries.
• Coordinate the proposal review process and incorporate feedback from internal stakeholders.
• Ensure proposal documents are formatted and branded correctly.
• Manage multiple proposals simultaneously while meeting strict deadlines.
• Track proposal metrics and incorporate feedback to improve future proposals.
• Support sales operations processes and initiatives.

Required Education and Experience:
• Bachelor’s degree or equivalent combination of education and experience may be considered
• Strong project management skills and ability to manage multiple projects simultaneously.
• Familiarity with complex proposal processes and RFP/RFI requirements.
• Excellent writing, editing, and proofreading skills.
• Ability to work independently and in a team environment.
• Strong interpersonal and communication skills.
• Proficiency in business software like Microsoft Office and PowerPoint
• Experience with Responsive or content management database
• At minimum 5 years or equivalent experience with proposal writing
• Benefits Administration industry experience
• 5+ years of project management experience
• Experience developing content in healthcare, financial, technical, or other complex industry is required
• Minimal travel may be required.

Why Join bswift?

At bswift, we empower our employees to make a meaningful impact, innovate, and grow. Joining our team means stepping into a collaborative and dynamic environment that values creativity, initiative, and a passion for client success. We are dedicated to fostering an inclusive workplace that celebrates diversity and values each team member’s unique contributions.

Benefits of Working at bswift:

• Comprehensive Health Benefits: Access to health, dental, and vision plans to support your wellness and that of your family.
• Competitive Compensation: A compensation package that recognizes your skills, experience, and contributions, including performance-based incentives for most roles.
• Remote first, Office friendly environment! No time to commute?  No problem!
• Retirement Savings Plans: Options to help you plan for a secure financial future with employer-sponsored retirement savings programs.
• Professional Development: Opportunities for career growth, including training and access to resources to support your career progression.
• Supportive Culture: A work environment that encourages collaboration, open communication, and creative problem-solving, where your voice and ideas are valued.
• Employee Wellbeing Initiatives: Programs focus