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.

What you will do:

• 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.

What you will bring:

• 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 offsite locations.

Other Skills:

• 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, NotebookLM) 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.

Location:

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. Your recruiter will share more details about our hybrid model. 

Pay & Benefits:

The anticipated new hire base salary range for this full-time position is $81,000-$100,000 + equity + benefits. 

Our salary ranges are based on the job, level, and location, and reflect the lowest to highest geographic markets where we are hiring for this role within the United States. Within this range, individual compensation is determined by a candidate’s location as well as a range of factors including but not limited to: unique relevant experience, job-related skills, and education or training. 
Your recruiter will provide more details on the specific salary range for your location during the hiring process.

At Headspace, base salary is but one component of our Total Rewards package. We’re proud of our robust package inclusive of: base salary, stock awards, comprehensive healthcare coverage, monthly wellness stipend, retirement savings match, lifetime Headspace membership, generous parental leave, and more. Additional details about our Total Rewards package will be provided during the recruitment process. 

About Headspace

Headspace exists to provide every person access to lifelong mental health support. We combine evidence-based content, clinical care, and innovative technology to help millions of members around the world get support that’s effective, personalized, and truly accessible whenever and wherever they need it.

At Headspace, our values aren’t just what we believe, they’re how we work, grow, and make an impact together. We live them daily: Make the Mission Matter, Iterate to Great, Own the Outcome, and Connect with Courage. These values shape our decisions, guide our collaborations, and define our culture. They’re our shared commitment to building a more connected, human-centered team—one that’s redefining how mental health care supports people today and for generations to come.

Why You’ll Love Working Here:

• A mission that matters—with impact you can see and feel
• A culture that’s collaborative, inclusive, and grounded in our values
• The chance to shape what mental health care looks like next
• Competitive pay and benefits that support your whole self

How we feel about Diversity, Equity, Inclusion and Belonging:

Headspace is committed to bringing together humans from different backgrounds and perspectives, providing employees with a safe and welcoming work environment free of discrimination and harassment. We strive to create a diverse & inclusive environment where everyone can thrive, feel a sense of belonging, and do impactful work together. 

As an equal opportunity employer, we prohibit any unlawful discrimination against a job applicant on the basis of their race, color, religion, gender, gender identity, gender expression, sexual orientation, national origin, family or parental status, disability*, age, veteran status, or any other status protected by the laws or regulations in the locations where we operate. We respect the laws enforced by the EEOC and are dedicated to going above and beyond in fostering diversity across our workplace. 

*Applicants with disabilities may be entitled to reasonable accommodation under the terms of the Americans with Disabilities Act and certain state or local laws. A reasonable accommodation is a change in the way things are normally done which will ensure an equal employment opportunity without imposing undue hardship on Headspace. Please inform our Talent team by filling out this form if you need any assistance completing any forms or to otherwise participate in the application or interview process.

Headspace participates in the E-Verify Program.

Privacy Statement

All member records are protected according to our Privacy Policy. Further, while employees of Headspace (formerly Ginger) cannot access Headspace products/services, they will be offered benefits according to the company's benefit plan. To ensure we are adhering to best practice and ethical guidelines in the field of mental health, we take care to avoid dual relationships. A dual relationship occurs when a mental health care provider has a second, significantly different relationship with their client in addition to the traditional client-therapist relationship—including, for example, a managerial relationship.  

As such, Headspace requests that individuals who have received coaching or clinical services at Headspace wait until their care with Headspace is complete before applying for a position. If someone with a Headspace account is hired for a position, please note their account will be deactivated and they will not be able to use Headspace services for the duration of their employment. 

Further, if Headspace cannot find a role that fails to resolve an ethical issue associated with a dual relationship, Headspace may need to take steps to ensure ethical obligations are being adhered to, including a delayed start date or a potential leave of absence. Such steps would be taken to protect both the former member, as well as any relevant individuals from their care team, from impairment, risk of exploitation, or harm.

For how how we will use the personal information you provide as part of the application process, please see: https://www.headspace.com/applicant-notice