Proposal Manager


SKYGEN is the trusted partner to deliver confidence and peace of mind to specialty benefit payers and government agencies responsible for the delivery and administration of specialty benefits. With cutting-edge technology solutions and expertly-driven third-party administration services, SKYGEN transforms benefits management and administration to reduce costs, increase healthcare value and elevate experiences and satisfaction for all stakeholders.

Position Details

Proposal Manager
Southeast Wisconsin
Menomonee Falls, WI

What are important things that YOU need to know about this role?

  • Position can be remote in the U.S. or based out of our Menomonee Falls, WI office (near Milwaukee)
  • Reports to the Chief Strategic Initiatives Officer and has one direct report
  • Visible role within the organization which provides exposure to our executive team
  • Manages the messaging to help secure additional business

What will YOU be doing for us?

The Proposal Manager leads the overall process for creating and managing proposals for new sales opportunities, including but not limited to, Request for Proposal (RFP), Request for Information (RFI), and proposals to extend our offerings with current customers. The Proposal Manager oversees a proposal response team; plans, directs, and coordinates activities for proposals; writes and edits proposal content; and submits responses within the required timeframes. With an in-depth knowledge of the specialty benefits industry and a deep understanding of customer business needs, the Proposal Manager collaborates with the Growth/Innovation team and SKYGEN senior executives to develop creative solutions to sales opportunities, and then translates those solutions into compelling, informed, tailored proposals that win new business.

What will YOU be working on?

  • Manage multiple proposals simultaneously while effectively managing scope, schedule, response quality, and internal and external resources.
  • Contribute to executive-level discussions to define the bid strategy and “win themes” for proposals and sales opportunities.
  • Set deliverable priorities, estimate work effort and resource requirements, coordinate efforts between the proposal team and subject matter experts, and guide and direct activities of participants throughout the proposal development process.
  • Develop and communicate content delivery schedules to meet proposal timelines, and follow up as needed, to ensure all proposal participants and subject matter experts deliver content and deliverables on time throughout the proposal lifecycle.
  • Lead the development, packaging, and delivery of proposals, including interviewing stakeholders; writing and editing responses to ensure readability, technical accuracy, and consistent tone and voice; assembling content, cost proposals, and other required documents and deliverables from subject matter experts; and delivering a polished, professional proposal that wins customers or opens the door to new opportunities.
  • Track proposal progress against deliverable timelines and provide regular status updates to stakeholders.
  • Manage proposal team department staffing, including FTE planning, hiring, and training.
  • Evaluate the performance of proposal team staff members and provide regular feedback on the quality, timeliness, and effectiveness of proposal development activities and interaction with other proposal participants and stakeholders.
  • Collaborate with individual proposal team staff members to design and implement personalized development plans designed to help recognize and retain high achievers, encourage and support the development of new skills, help guide progress toward career goals, and improve overall performance and job satisfaction.
  • Continuously improve the efficiency of the proposal process by researching and implementing best practices, and by building and maintaining a comprehensive resource library.
  • Continuously improve the company’s effectiveness in developing compelling proposals that result in winning new business by remaining informed about competitors and trends in the specialty benefits industry, and by analyzing the characteristics of winning – and losing – proposals to gain new insights.
  • Foster a work environment built on integrity, respect, accountability, and superior service.

Required Level of Education, Licenses, and/or Certificates:

  • Bachelor’s degree in Marketing, Journalism, Communications, Business or similar discipline or equivalent years of experience

Required Level of Experience:

  • 5+ years of professional experience in proposal writing or corporate communications.
  • 2 years of managing project teams, resources and multiple resources

Required Knowledge, Skills, and Abilities:

  • Expert skills with Microsoft Office Suite
  • Excellent verbal and written communication skills.
  • Strong proof reading skills.
  • Ability to translate broad, complex concepts from subject matter experts into clear, compelling and concise communication.
  • Ability to prioritize workload and balance multiple priorities 
  • Demonstrated project management skills.

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