Director of Product Marketing and Proposals

The Role

​​TimelyCare is seeking a strategic and collaborative Director of Product Marketing and Proposals to lead and scale the product marketing function, ensuring strong go-to-market execution, compelling positioning, and high-impact proposals that fuel both customer acquisition and retention. 

The ideal candidate is a cross-functional leader who thrives at the intersection of product, sales, marketing, and strategy.

• Go-to-Market Leadership
• Own the end-to-end GTM process for new product launches and key feature enhancements.
• Guide customer segmentation, persona development, and campaign targeting strategies.
• Develop frameworks and tools that elevate the sales enablement function (e.g., messaging guides, battlecards, pitch decks).
• Support customer lifecycle strategies and contribute to retention-focused campaigns.
• Proposal & RFP Oversight
• Oversee the proposal management process (RFPs, RFIs, RFQs), ensuring timely, strategic, and winning responses.
• Align proposal content with broader product marketing messaging and strategic positioning.
• Maintain up-to-date content libraries and collaborate across departments to gather key inputs.
• Market Intelligence & Insights
• Lead competitive analysis and synthesize insights to inform product positioning and differentiation.
• Champion the voice of the customer and surface market trends that inform roadmap and campaign planning.
• Leadership & Team Development
• Lead and mentor a team of product marketers.
• Define and refine our product marketing strategy, aligning with GTM goals across new logo acquisition, expansion, and customer retention.
• Oversee proposal strategy and execution, ensuring quality, accuracy, and strategic fit of responses.
• Serve as a champion for leveraging AI-powered tools to  streamline workflows, personalize communications, and accelerate content development.
• Partner closely with Product, Growth, Sales, and Customer Success to define value propositions, develop competitive positioning, and ensure strong internal alignment.
• Performs additional tasks and projects as needed to support the evolving needs of team objectives and company goals. 

• At least 10 years of experience in product marketing, marketing strategy, or proposals, including 3–5 years in a leadership role.
• Bachelor’s Degree in Marketing, Business, Communications or related field. Masters preferred. 
• Experience working in higher education, K-12, edtech SaaS, or digital health strongly preferred.
• Proven ability to lead and scale high-performing teams.
• Experience working cross-functionally with Sales, Product, and Customer Success teams to execute strategic initiatives.
• Strong communicator with demonstrated success in messaging, positioning, and go-to-market planning.
• Exceptional organizational and project management skills; comfortable leading through ambiguity and shifting priorities.
• Strong understanding of proposal development and public-sector procurement processes is a plus.
• Data-driven mindset, with strong analytical skills.

• Passionate about health and wellbeing more accessible for students and institutions.
• A team builder who mentors and uplifts others.
• Highly collaborative, with excellent communication skills and the ability to build strong relationships and trust across teams and levels.
• Strategic thinker with the ability to balance vision with execution. Highly accountable.
• Comfortable navigating a fast-paced, remote first organization with evolving priorities, bringing creative, data-driven solutions to complex problems.
• Committed to diversity, equity, and inclusion, ensuring that marketing efforts reflect and support diverse student populations.

• Paid Company Holidays + No work on your birthday!
• Flexible PTO + Volunteer Time Off (VTO) as an organization to give back to the community
• Variable bonus eligibility on a quarterly basis
• Company-sponsored Health Insurance (Medical, Dental, Vision) + Pet Insurance 
• Company-paid group Life Insurance + Company-paid Short Term Disability
• Concierge benefit support services
• 401(k) with employer match 
• Free access to TimelyCare virtual medical and mental health support 
• Mission-Driven Purpose with a Supportive Team Culture

The salary range for this opportunity is $155,000 – $165,000 per year, depending on education and experience. This is the base pay. You will be eligible for a discretionary bonus in addition to the base pay, to be discussed during the interview process.