Castlight Health

Proposals Director

United States full-time Executive $131,243 - $196,865
full-time Executive level Technology & IT Salary listed Curated
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About the role

Job Description Summary
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Serves as a leader within the organization's proposals function, with primary focus on proposal content strategy, development, and infrastructure. Acts as a leading expert on content strategy, response quality, and content management, partnering closely with proposals leadership and contributing hands-on to select high-priority pursuits. Helps shape the function's content strategy and operating model to elevate the organization's ability to win through superior proposal execution.

The Proposals Director drives short- to mid-term strategy for proposal content and infrastructure and exercises independent judgment on novel, cross-functional problems. This job operates as a subject-matter expert across multiple functional areas, designing content strategies and response frameworks where no established precedent exists within the function, and influences both functional and cross-functional strategy in partnership with proposals leadership.‎
How will you make an impact & Requirements
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KEY RESPONSIBILITIES
Partner across proposals leadership to define proposals function strategy, including intake prioritization and quality standards, with primary ownership of the content management architecture and technology roadmap.
Contribute hands-on content strategy, narrative development, and quality assurance support on the organization's most strategically important proposals, partnering with pursuit leads as needed.
Own the design, architecture, and continuous improvement of a scalable content management system that gives the sales organization rapid access to accurate, compelling response content.
Lead the development of enterprise proposal standards, style guides, and review processes that raise the quality and consistency of all client-facing submissions.
Partner with sales, clinical, and marketing leadership to align proposal content and messaging with commercial strategy and value priorities.
Mentor proposals team professionals in function & content strategy, writing craft, and content library practices, partnering with proposals leadership on broader team expectations and development.

QUALIFICATIONS
Bachelor's degree required; 10+ years of experience in proposal management or sales support strategy in healthcare, managed care, or health technology.
Demonstrated track record of building and scaling proposal content strategy, libraries, or knowledge management infrastructure, with accountability for response quality and win rates.
Expert writing and editorial skills with the ability to craft and evaluate executive-level proposal narratives.
Deep knowledge of healthcare procurement processes, RFP structures, and payer buying dynamics.
Experience with proposal management platforms and content management infrastructure at scale.
MBA or advanced degree preferred.
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Compensation Range:
$131,243.00to
$196,865.00The anticipated base salary range represents the Company's good-faith estimate of the compensation it reasonably expects to pay for this position at the time of posting. Actual compensation will be determined based on factors including experience, skills, qualifications, geographic location, internal equity, and business needs.
Originally posted on Himalayas

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Executive
Technology & IT Sales Writing Proposals Director Technology Executive level

Likely questions

  1. Tell us about work you have done that is close to the Proposals Director role.
  2. How would you approach your first 30 days at Castlight Health?
  3. Which of Sales, Writing and Proposals have you used recently, and what did it help you achieve?
  4. How have you led people, improved a process, or made a hard decision in a previous role?
  5. How do you handle busy days, changing priorities, or pressure at work?

Prepare before the call

  • A recent example that proves your experience with Sales, Writing and Proposals.
  • One short story with a problem, your action, and the result.
  • Two examples that show the strengths listed on your CV.
  • A clear reason why this role and company interest you.
  • Your availability, preferred work style, and salary expectations.

Ask them

  • What would success look like in the first 90 days?
  • What are the main problems this hire should help solve?
  • How does the team give feedback and measure good work?
  • What does a normal working week look like for this role?
Practice line

I am interested in the Proposals Director role because I can bring practical experience in Sales, Writing and Proposals, learn the team quickly, and contribute to the outcomes Castlight Health needs from this hire.

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