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VP of Marketing

May 29, 2026

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 <ul class="[li_&]:mb-0 [li_&]:mt-1 [li_&]:gap-1 [&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc flex flex-col gap-1 pl-8 mb-3"> <li class="font-claude-response-body whitespace-normal break-words pl-2">Own end-to-end B2B demand generation strategy — from awareness through pipeline creation — across broker, consultant, and employer segments</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Design and operate a content-driven ABM engine that targets high-value accounts with precision and scale</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Build and manage a full ABM tech stack including intent data, account scoring, personalization, and orchestration tools</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Partner closely with Sales and SDR leadership to ensure marketing programs translate directly into pipeline and revenue</li> </ul> Paid Media & Digital Programs <ul class="[li_&]:mb-0 [li_&]:mt-1 [li_&]:gap-1 [&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc flex flex-col gap-1 pl-8 mb-3"> <li class="font-claude-response-body whitespace-normal break-words pl-2">Lead paid media strategy and execution across digital display, SEM, CTV, LinkedIn, and programmatic</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Manage multimillion-dollar media budgets with a focus on measurable pipeline contribution and CAC efficiency</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Continuously optimize channel mix and creative based on performance data</li> </ul> Content & Nurture <ul class="[li_&]:mb-0 [li_&]:mt-1 [li_&]:gap-1 [&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc flex flex-col gap-1 pl-8 mb-3"> <li class="font-claude-response-body whitespace-normal break-words pl-2">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</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Build and own SDR sequences and marketing nurture programs that keep prospects engaged across long sales cycles</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Own website strategy and optimization, including conversion rate improvement and intent-signal activation</li> </ul> AI & Marketing Technology <ul class="[li_&]:mb-0 [li_&]:mt-1 [li_&]:gap-1 [&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc flex flex-col gap-1 pl-8 mb-3"> <li class="font-claude-response-body whitespace-normal break-words pl-2">Champion the use of modern AI tools across the function — from content production to campaign optimization to intent signal analysis</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Maintain and evolve the marketing tech stack to ensure the team is operating with best-in-class tools and workflows</li> </ul> Team Leadership <ul class="[li_&]:mb-0 [li_&]:mt-1 [li_&]:gap-1 [&:not(:last-child)_ul]:pb-1 [&:not(:last-child)_ol]:pb-1 list-disc flex flex-col gap-1 pl-8 mb-3"> <li class="font-claude-response-body whitespace-normal break-words pl-2">Lead and develop a high-performing marketing team that executes across channels with speed and accountability</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Define team structure, role scope, and future hiring needs as the company scales</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Report to the CMO; partner closely with Sales, Product, and Operations leadership</li> </ul> What You'll Bring <ul> <li class="font-claude-response-body whitespace-normal break-words pl-2">10+ years of B2B marketing experience, with at least 5 years in a senior leadership role</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Deep expertise in demand generation and ABM</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Proven track record managing multimillion-dollar paid media budgets</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Experience working alongside SDR/BDR teams</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Fluency with modern AI tools and a clear point of view on how to apply them across a B2B marketing function</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">A builder's mentality — you thrive where infrastructure still needs to be created</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Strong analytical skills and comfort using data to make decisions and report on performance</li> <li class="font-claude-response-body whitespace-normal break-words pl-2">Executive presence — you can represent marketing credibly to C-level stakeholders and board audiences</li> <li class="whitespace-normal break-words pl-2">Bachelor's degree required</li> </ul> What You'll Get <ul> <li>Competitive salary, uncapped incentive bonus, and equity package </li> <li>Comprehensive Medical, Dental, and Vision benefits </li> <li>A 401k retirement plan </li> <li>Paid vacation and company holidays </li> <li>Opportunity to make an impact at a rapidly growing mission-driven company transforming healthcare in the U.S. </li> </ul><div class="content-conclusion">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.</div>

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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...