Head of Marketing

About the Role

Goal for this Role

We’re hiring a Head of Marketing to build and execute Truemed’s marketing strategy from the ground up across both B2C and B2B2C channels. This role will be responsible for driving consumer growth by activating demand from HSA/FSA cardholders, while also enabling our brand partners to effectively communicate and market Truemed to their customers. Success in this role requires deep experience in direct-to-consumer marketing, strong partner enablement instincts, and the ability to scale performance-driven campaigns that unlock net-new revenue for both Truemed and our partner ecosystem.

Outcomes for this Role

1. Drive direct growth through paid and performance channels. Own the strategy and execution of full-funnel acquisition across mediums like Google Ads, Meta, TikTok, YouTube, and other platforms. This includes optimizing SEM and paid social to convert high-intent shoppers, managing affiliate relationships to scale partner-sourced traffic, and building influencer programs that educate consumers and boost brand credibility around HSA/FSA eligibility. You will design experiments to improve CAC, funnel conversion, LTV, and GMV.

2. Equip merchant partners with powerful, scalable marketing support. Collaborate closely with Truemed brand partners to maximize visibility and performance. This includes hands-on support in co-developing campaigns and messaging (1:1), as well as delivering easy-to-use, plug-and-play assets, toolkits, and educational content that enable partners to promote HSA/FSA offerings at scale across their own marketing channels (1:many).

3. Unlock new distribution channels via ecosystem partnerships. Build and execute marketing strategies that amplify Truemed’s reach through partnerships with Third Party Administrators (TPAs), benefits platforms, and large employers. This involves creating tailored campaigns, internal comms collateral, onboarding flows, and go-to-market playbooks that help institutional partners drive HSA/FSA consumer adoption from within their networks.

4. Steward the Truemed brand and consumer trust. Own the tone, messaging, and market presence of the Truemed brand, ensuring consistency, clarity, and authority in everything from paid ads to educational content. You will position Truemed as a trusted advisor in the health and wellness space, helping consumers make informed decisions about how to use HSA/FSA funds to support healthier lives.

What We’re Looking For in a Marketing Leader

Relentless Experimentation & Growth Mindset

Demonstrated ability to rapidly test, learn, and iterate. You know how to design smart experiments to improve CAC, funnel conversion, LTV, and GMV and aren’t afraid to fail fast in pursuit of efficient scale.

Cross-Functional Collaboration with Product

Partner closely with our Product and Engineering teams to continuously optimize the user journey, identify and reduce drop-off points, and improve conversion through UX/UI refinements, messaging, and A/B testing.

AI-Native Marketing Thinking

Use AI as an accelerator across workflows, from creative testing and content generation to campaign optimization, insight extraction, and performance analysis. You see AI not as a tool, but as an enabler for velocity and scale.

Data-Driven Decision Making

Build dashboards and real-time reporting frameworks that surface actionable insights and align the team around measurable goals. You balance instinct with analysis and use data to drive both strategic and tactical decisions.

Full-Funnel Ownership

Think holistically from first impression to repeat purchase. You understand how acquisition, conversion, retention, and reactivation work together and you’re excited to own and optimize across the entire funnel.

Customer-Centric Mentality

You think from the user’s point of view and understand how to communicate the value of HSA/FSA in a way that inspires action and builds long-term trust across both consumers and brand partners.

What You Bring

• 5–8 years of full-funnel growth marketing experience, with a proven track record of driving measurable results across performance channels (SEM, paid social, affiliate, influencer).
  

• Deep hands-on expertise in campaign management across platforms like Google Ads, Meta, TikTok, and YouTube - comfortable leading strategy, execution, and optimization.
  

• Strong analytical acumen, with the ability to build and interpret CAC, LTV, and GMV models to inform investment decisions and performance benchmarks.
  

• Experience supporting B2B2C or marketplace ecosystems, particularly in collaborating with external partners to drive co-marketing, asset development, and performance enablement at scale.
  

• Comfort working cross-functionally, especially with Product, Engineering, and external partners to align marketing goals with product UX and revenue outcomes.
  

• Creative, resourceful, and fast-moving, with a growth mindset and an eagerness to experiment, learn, and refine strategies quickly.
  

• Bonus: Familiarity with health, wellness, or benefits-driven platforms, or past work in regulated environments (e.g. healthcare, fintech, insurance).

Compensation Range: $175k - $260k