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.

What You'll Do

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.

What You Bring

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.

Who You Are

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.

Benefits + Perks

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