Proposal Manager

About the Proposal Manager at Headspace

Proposal Managers at Headspace are storytellers who sit at the intersection of strategy and execution. As key drivers of our growth, you will be responsible for delivering high-quality responses to RFPs and RFIs, serving as the bridge between sales goals and technical capabilities. In this role, you will also own sections of the proposal content database, ensuring our messaging remains sharp and aligned with our evolving product suite.

This is a critical position focused on achieving revenue targets in partnership with a broad cross‑functional team—including Sales, Product, Compliance, Leadership, and many others.

• Lead and project manage the end‑to‑end RFP/RFI process, from initial intake to final submission, in partnership with Sales leaders and Account Managers.
• Draft persuasive, clear, and differentiating content that aligns with Headspace’s brand voice and unique market positioning.
• Intake, assess, and triage RFPs from employers, consultants, and health plans, developing case‑specific “win strategies” alongside Sales leadership.
• Support the sales team with post‑proposal follow‑up questions and additional documentation.
• Own and maintain assigned sections of the proposal content database, ensuring all technical and product information is accurate and up to date.
• Refresh messaging to reflect ongoing product enhancements, outcomes, and evolving market trends.
• Build strong cross‑functional relationships with internal Subject Matter Experts (SMEs) and external business partners to streamline information gathering.
• Coordinate across departments—including Finance, Legal, Security, and Care teams—to ensure proposal content meets compliance and technical standards.
• Manage competing priorities to consistently meet all internal and external deadlines.
• Support ad‑hoc projects and take on additional responsibilities as the Proposal team evolves.

• 3+ years of experience responding to healthcare benefit RFPs, RFIs, or complex sales requests. (Required)
• Deep industry expertise in EAP, behavioral health, health insurance, or wellness, with a strong understanding of the employer and benefit consultant sales cycle. (Required)
• Proven track record as a Proposal Manager, Analyst, Writer, or Bid Manager. (Required)
• Mission‑aligned professional with prior experience in mental health, wellbeing, health plan, or broader employee benefit sectors.
• Bachelor’s degree in English, Communications, Journalism, Business, Marketing, or a related field.
• Ability to work effectively in a remote setting, with the flexibility for occasional travel (1–2 times per year) to Headspace’s California headquarters or other off‑site locations.

• Exceptional Communication:
  Superior writing, editing, and storytelling skills, with the ability to translate complex technical concepts into persuasive sales narratives.
• Advanced Project Management:
  Proven ability to work independently and collaboratively while navigating multiple, high‑priority, deadline‑driven projects.
• Tech‑Forward Mindset:
  High proficiency in GSuite, MS Office (Word, Excel, PowerPoint), and Adobe Acrobat Pro.
• Modern Tooling:
  Hands‑on experience with AI tools (e.g., ChatGPT, Gemini, Notebook
  
  LM) and proposal management software (e.g., Responsive, Loopio, Qvidian).
• Procurement Expertise:
  Familiarity with consultant, broker, and employer online procurement systems and portals.
• Agility & Adaptability:
  Experience thriving in dynamic, early‑stage, or high‑growth environments with a proactive approach to managing market shifts and organizational change.
• Stakeholder Management:
  Strong relationship‑building skills with the ability to influence and partner across various levels of an organization.

We are currently hiring this role remotely in the US and Hybrid for San Francisco (SF). Candidates must permanently reside in the US full‑time. For candidates with a primary residence in the greater SF area, this role will follow our hybrid model. You’ll work 3 days per week from our office, allowing for impactful in‑office collaboration and connection, while enjoying the flexibility of remote work for the rest of the week.

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