Head of Brand and Marketing

The role

Reports to the Chief Growth Officer. Seed-stage: post-product, post-traction, accelerating.

• You will establish Smirk as the category-defining brand for Mobile Health Benefits—the one finally built for the modern worker.
• This is not a role for someone who wants a playbook handed to them. The playbook does not exist yet. You will help write it.
• You will own everything from brand positioning to ROAS, from Smirkhealth.com to earned media, from the creator strategy to the first breakthrough campaign.
• You will lead a small team, build new capabilities from the ground up, and set the standard for creative excellence and commercial impact.
• You will roll up your sleeves and get into the details, inspire the team to play to win, and implement creative ideas that fuel rapid growth and drive low-cost, viral customer acquisition.
• Seed-stage means: small team, real ambiguity, no roster of agencies waiting. Outcomes over optics. If that energizes you, keep reading.

What you'll own

Brand stewardship

• Own positioning, brand strategy, brand management, and the brand playbooks that scale as we grow.
• Establish Smirk as the category creator of Mobile Health Benefits—a genuine alternative to traditional health insurance, not another competitor within it.
• Get people talking about Smirk organically on social as the brand that finally built health benefits for the modern worker.

Marketing-led growth

• Drive marketing-led growth across paid, partner, social, owned, and earned channels.
• Own brand awareness, engagement, acquisition, retention, and advocacy end to end.
• Own ROI and ROAS, and optimize mix across channels and funnel stage. Set ambitious targets and hit them.

Integrated marketing programs

• Develop and execute end-to-end integrated marketing programs across upper, middle, and lower funnel.
• Lead the strategy and execution for Smirkhealth.com as a positioning surface, an engagement surface, an activation surface, and a growth surface.
• Ship on a cyclical, iterative basis with clear hypotheses, disciplined testing, and a clear path to scale.

Creative strategy and production

• Build the strategy, development, and evolution of a durable, compelling, and differentiated creative platform for the Smirk brand.
• Manage internal and external resources to drive high-quality creative production at scale across B2C and partner marketing assets.

Team and capability building

• Lead a small team of expert marketers today; build new marketing capabilities as the business scales.
• Set high standards of excellence in execution and elevate everyone around you.
• Bring a clear roadmap for building agency partnerships and internal capability over time.

Consumer insight

• Drive consumer insights that unlock growth for the total business.
• Bring an outside-in perspective to the leadership table. Always lead with the customer.

Who we're looking for

We're looking for a senior marketing leader who has built the brand and the engine at the same time.

• 15+ years in marketing with a track record of driving growth for a B2C brand.
• Proven commercial track record. You have led marketing-driven growth and can point to the number, the tactics, and the insights that changed the growth trajectory of a brand and business.
• This is a builder's seat. We want someone with the résumé and, more importantly, the operator instincts to build the campaigns and the business result—ideally within insurance or other subscription-based services.
• Strong brand credentials. Brand strategy, brand positioning, and brand management are core disciplines you have practiced at depth.
• Deep experience in social and earned. You have developed breakthrough ideas that moved culture and metrics, not just impressions.
• Demonstrated success building and executing integrated marketing campaigns that moved the needle on full-funnel consumer metrics.
• Commercial fluency. You connect marketing plans to business strategy and financial outcomes.
• Full-funnel channel depth across paid, partner, owned, and earned, from media to creative; deep experience in paid social and search a plus.
• Growth mindset. Hypothesis-driven, disciplined about test, learn, and scale.
• Customer-first. You build plans starting with the customer and refine them based on customer signals.
• Creative instincts. You are an engine room of ideas and you know what great creative looks like.
• A leader who inspires. You motivate, manage, and elevate the people around you.

Key attributes

• Lead from the front. Small team, real ambiguity, capabilities to be built from the ground up. You will be in the work.
• Play to win. Set ambitious goals. Create belief. Inspire the team to be better every cycle.
• Creative to the core. You think creatively, you push for creative excellence, and you are the engine room of ideas for the business.
• Builder's mindset. Seed-stage means no roster of agencies handed to you and no playbook waiting on the shelf. You are strategic and scrappy in equal measure, with a clear roadmap to build as the business scales.

Why this role, why now

• The American healthcare benefits system was built for a workforce that no longer exists—one job, one employer, full-time, forever. Ninety million workers today are independent 1099 professionals, gig, part-time, multi-income, or micro-shifting. The system wasn't built for them.
• Smirk is building the infrastructure that fixes this. We have the carriers, the payment rail, the employer pipeline, and a C-suite advisory council of former CHROs from some of the largest workforces in the country. What we don't have yet is a brand that Americans recognize as the answer. That is what you will build.
• This is a seed-stage seat with the upside, the ambiguity, and the responsibility that comes with one. If you have spent 15+ years getting sharp on brand and growth and you are ready to point those skills at something that actually matters, this is the role.

Compensation and benefits

• Competitive base, calibrated to seed-stage and your experience.
• Meaningful early-stage equity with standard vesting.
• Health coverage (Smirk) and flexible PTO.
• Austin, NYC, or San Francisco. Hybrid.

About Smirk

• Smirk is building the AI health benefits infrastructure for the modern workforce: mobile, personalized coverage delivered with radical clarity. One in three adults today earns income from multiple sources, and traditional employer-tied benefits have failed the 90M+ workers who are independent 1099, flexible, gig-based, part-time, or between jobs.
• Our platform—the Smirk Wallet™ and Ailene™ AI care concierge—unifies coverage, payments, and care navigation into one intelligent system. We are carrier-backed (Chubb), Mastercard-partnered, live with Freelancers Union, and in active pilot design with Fortune 500 employers.
• We are seed-stage, post-product, post-traction, and accelerating. The brand and marketing engine is being built right now. Not tuned, not scaled. Built. We want a builder in the room while we do it.