VP of Marketing

Sidecar Health is redefining health insurance. Our mission is to make excellent healthcare affordable and accessible for everyone. We know that to accomplish this lofty mission, we need driven people who will make things happen.

The passionate people who make up Sidecar Health’s team come from all over, with backgrounds as tech leaders, policy makers, healthcare professionals, and beyond. And they all have one thing in common—the desire to fix a broken system and make it more personalized, affordable, and transparent.

If you want to use your talents to transform healthcare in the United States, come join us!

About the Role

We're looking for a Vice President of Marketing to lead the engine that drives our B2B growth. This is a senior leadership role for someone who has done this before — built demand gen infrastructure from scratch, managed multimillion-dollar budgets, run ABM programs at scale, and knows what a modern B2B marketing stack looks like.

Sidecar Health sells to employers, but our go-to-market is more complex than that. Brokers and benefits consultants are often the primary buying influence. Key employees shape internal decisions. And our members — the people actually using the product — are a constituency that a great VP of Marketing will understand deeply, even if they're not the primary audience for this role.

You'll be energized by the combination of creative strategy and operational rigor, and comfortable in a fast-moving environment where infrastructure still needs to be built, not just maintained.

What You'll Do

Demand Generation

• Own end-to-end B2B demand generation strategy — from awareness through pipeline creation — across broker, consultant, and employer segments

• Design and operate a content-driven ABM engine that targets high-value accounts with precision and scale

• Build and manage a full ABM tech stack including intent data, account scoring, personalization, and orchestration tools

• Partner closely with Sales and SDR leadership to ensure marketing programs translate directly into pipeline and revenue Paid Media & Digital Programs

• Lead paid media strategy and execution across digital display, SEM, CTV, LinkedIn, and programmatic

• Manage multimillion-dollar media budgets with a focus on measurable pipeline contribution and CAC efficiency

• Continuously optimize channel mix and creative based on performance data Content & Nurture

• Develop a content strategy that supports every stage of the buyer journey — from first touch to close — with assets built for broker, Regional Sales Manager (RSM), and employer audiences

• Build and own SDR sequences and marketing nurture programs that keep prospects engaged across long sales cycles

• Own website strategy and optimization, including conversion rate improvement and intent-signal activation AI & Marketing Technology

• Champion the use of modern AI tools across the function — from content production to campaign optimization to intent signal analysis

• Maintain and evolve the marketing tech stack to ensure the team is operating with best-in-class tools and workflows Team Leadership

• Lead and develop a high-performing marketing team that executes across channels with speed and accountability

• Define team structure, role scope, and future hiring needs as the company scales

• Report to the CMO; partner closely with Sales, Product, and Operations leadership What You'll Bring

• 10+ years of B2B marketing experience, with at least 5 years in a senior leadership role

• Deep expertise in demand generation and ABM

• Proven track record managing multimillion-dollar paid media budgets

• Experience working alongside SDR/BDR teams

• Fluency with modern AI tools and a clear point of view on how to apply them across a B2B marketing function

• A builder's mentality — you thrive where infrastructure still needs to be created

• Strong analytical skills and comfort using data to make decisions and report on performance

• Executive presence — you can represent marketing credibly to C-level stakeholders and board audiences

• Bachelor's degree required What You'll Get

• Competitive salary, uncapped incentive bonus, and equity package

• Comprehensive Medical, Dental, and Vision benefits

• A 401k retirement plan

• Paid vacation and company holidays

• Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. Sidecar Health is an Equal Opportunity employer committed to building a diverse team. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status or disability status.