Finally.Health Benefits Built for the Modern Worker.
Every American deserves affordable health benefits that provide access to high-quality care, whether they work full-time, part-time, independently or across multiple jobs.
Underwritten and insured by Federal Insurance Company and ACE American Insurance Company, both companies.
Health benefits were built for a different way of working.
By 2027 90 million Americans will work across part-time roles, changing schedules, 1099 careers, freelance projects, seasonal work, multiple employers and gig platforms.
The old system was built around jobs, eligibility rules and employment status, not the individual, leaving millions without health benefits they can afford, understand or use. That’s why Smirk exists.
Our vision.
Our vision is an America where every person can access affordable, high-quality care, no matter how they earn a living.
Healthcare should move with people, not disappear when their job changes.
Our mission.
Our mission is to build the next generation of health benefits around the individual, designed for how people work and live today.
We use AI for good to make health benefits more personalized and transparent, helping people understand what their benefits pay and what care may cost so they can make confident decisions with greater ownership, clarity, control and personal agency.
Our values.
Your health benefits should be built around your life and move with you as your job, hours or how you work changes.
Individuals should have greater agency over the benefits they choose and how they use them.
People deserve to understand what their benefits provide and what to expect before they receive care.
Benefits, care navigation, diagnostics and payments should work together, with AI-powered guidance helping people understand their benefits, navigate care and determine their next best action.
Built from our founder’s personal healthcare experience.
Healthcare became personal for Felix long before Smirk existed. Watching his family care for his brother through a serious heart condition showed him how an already difficult experience can be made even harder by navigating care, benefits and costs.
My brother has relied on a pacemaker since childhood. That’s when benefits stopped being abstract, and became personal.
Felix W. Ortiz III · Co-Founder, CEO & Chairman
Finally.Mobile Health Benefits by Smirk.
A new benefits model and the infrastructure for delivering it.
Smirk re-engineered the fixed-benefit health plan and combined it with an agentic technology layer to make affordable, high-quality care more accessible.
Personalized benefits, a personal AI patient advocate, pricing transparency and patient-to-provider payments work together in one connected experience, giving people greater clarity, control and personal agency over their healthcare.
Smirk was built around the individual, giving people greater freedom, control and ownership over their health benefits as work and life change.
Built by people who have lived the problem.
“Healthcare became personal for me long before Smirk existed. Growing up in Brooklyn, New York, my family had to navigate the complexity of care, benefits, and costs surrounding my brother’s serious heart condition. That experience stayed with me. I founded Smirk with a simple belief: healthcare should be built around people. By bringing benefits, payments, care navigation, and AI-powered guidance into one experience, we’re giving individuals greater clarity, control, and agency over their health.”
“I’ve spent my career inside healthcare, seeing firsthand how frustrating and unnecessarily complicated the system can be for both patients and providers. Too much time and energy gets wasted trying to understand what something costs, what’s covered, who owes what, and why getting paid or getting care has to be so difficult. The longer I’ve worked in it, the less willing I’ve become to accept ‘this is just how healthcare works’ as an answer. We can do better, and I want to be part of proving that.”
“Healthcare should be a commodity. You should be able to get care the way you get anything else that works: know what it costs, know it’s covered, move on with your day. Instead it’s a second job - one that arrives at the exact moment you have the least capacity for it. I joined Smirk because we’re building the opposite of that: an AI concierge that actually knows your plan and your situation, so instead of decoding a system, you just ask and get an answer. That’s the rare kind of problem where the hardest engineering and the most obvious good point in the same direction, and there’s no better time to go after it.”
“Healthcare should be built around people, not a system they have to fight their way through. I know what it feels like to need care and be left navigating the financial consequences on your own. No one should have to choose between getting the care they need and protecting their financial future. That’s why Smirk’s mission is so personal to me. We’re building a simpler, more accessible and affordable healthcare experience that gives people the clarity, control and agency I wish I’d had when I needed it most.”
“I love building products that help people make decisions that truly matter. In those moments, people deserve to feel clear about their choices, supported through the process, and confident about what comes next. At Instacart, designing products for more than 300,000 shoppers opened my eyes to how many freelancers, gig workers, and other independent workers can’t count on healthcare through their jobs. That stayed with me. I joined Smirk because reliable access to healthcare shouldn’t depend on fitting into a traditional employment model. We have the chance to build something genuinely new: coverage people can understand, trust, and rely on - no matter how they make a living.”
“Access and affordability of care is a generational problem that is being exacerbated by changes in how people work and policy gridlock in Washington. I’ve also personally experienced the challenges navigating the system when you sit outside of the traditional employer-dependent group health insurance ecosystem. I joined Smirk because it gives me an opportunity to help build the solution from the ground up, and make a real difference in the lives of our customers.”
“My wife and I have owned a small business for over 20 years and have employed hundreds of local women. During this period many of them have had challenges understanding their health insurance and affording healthcare. My passion lies with utilizing my health insurance experience to create meaningful solutions for this underserved workforce in America. Solutions which provide plans customized to meet their needs, cost transparency of the benefits, provider costs and member cost, and create unmeasurable consumer confidence to help people take better care of themselves. I joined Smirk to make a difference!”
“As a father of three under three, I spend practically every week at the pediatrician dealing with something unexpected, so I know how overwhelming healthcare friction can be when you’re just trying to take care of your family. Coming from Lemonade, I’ve seen how insurance can be redesigned to be delightfully simple, transparent, and empathetic. I joined Smirk to bring that same seamless experience to healthcare, so parents and patients can focus on getting better rather than deciphering the system.”
“Growing up, conversations around healthcare access is what guided almost every career decision for my friends and family. The fear of what would be covered, and catastrophic stories of when it wasn’t. I’m passionate about finding ways to broaden access. Healthcare should feel simple and painless.”
“Growing up in a family of physicians, healthcare was never abstract to me. I saw the compassion, judgment, and commitment providers bring to caring for people—and how often the system surrounding that care makes their work, and their patients’ lives, harder than it needs to be. The experience around healthcare should reflect the care itself: personal, trustworthy, and focused on helping people feel better, not leaving them confused about coverage, costs, or what to do next. I joined Smirk because we have the opportunity to remove that friction and build a simpler, more transparent healthcare experience that works better for both patients and providers.”
“I’ve been the person without coverage - laid off, then in an accident, sitting there doing math in my head about whether I could afford to be seen. What I remember isn’t the injury, it’s the calculation. You start weighing whether something is bad enough to justify the bill, and that’s a terrible position to put anyone in. Nobody should have to decide whether they can afford to take care of themselves. Getting to work on something that takes even a little of that dread off someone’s plate is why I’m here.”
“I’ve seen how quickly healthcare can go from something you barely think about to something that takes up way too much mental space, especially when you don’t know what something will cost or what’s actually covered. I love the idea that your health benefits can actually give you more freedom to work how you want, live how you want, and make choices without healthcare holding you back - and that’s what I hope Smirk can give more people.”
“I grew up in England. I never thought about what it cost to see a doctor, and I didn’t know what a deductible was. If I needed an x-ray, it was just there for my next doctor to pull up. It all connected. Then I moved to the US and had to figure the system out cold, as an adult, with none of the instincts most people here grow up with. I said yes to a few extra tests thinking they were covered. A surprise bill showed up weeks later, and once I paid it, another one followed. The whole thing felt built to keep you guessing. That’s why I joined Smirk. Benefits you actually own, where you know what you’ll pay and what you’re covered for, so you can do the quick math and get on with your life.”
“Healthcare shouldn’t require a manual. I joined Smirk because I love the idea of taking something unnecessarily complicated and making it simple, transparent, and genuinely useful for people when they need it most.”
“Going through different situations in my life where I’ve had to deal with health insurance, coverage, expenses, reimbursements, and the complexity of the whole system has made me truly appreciate when insurance is intuitive, transparent, accessible, and simply easy to navigate. Especially when you’re dealing with a real-life situation and need to make decisions quickly, the last thing you want is to spend time trying to understand how the system works. I joined Smirk because I believe we can bring that kind of seamless experience into people’s lives when they might need it most.”
“I’ve experienced how quickly healthcare can become overwhelming when you’re trying to understand what’s covered, what something will cost, and what you’re actually supposed to do next. As a designer, I love the challenge of taking that kind of complexity and making it feel simple, intuitive, and even a little fun. I joined Smirk because I want to help create an experience where people feel supported and in control, especially when the last thing they need is more complexity.”
“Growing up in Croatia, I never had to think about what a doctor’s visit cost. Coming to the US system as an engineer, what stands out is how much of the complexity people navigate is accumulated rather than designed — layers that built up over decades and were never worth anyone’s time to untangle. That’s the kind of problem I like working on: rebuilding something so the person using it doesn’t have to understand the mess underneath.”
“We’ve all had those moments when life throws a challenge your way, and healthcare only adds paperwork, bureaucracy, and uncertainty at the worst possible time. Having been there far too often - as both a daughter and a mom - I firmly believe healthcare should lighten the load, not add to it. I’ve always been passionate about simplifying complex systems through thoughtful design and continuous improvement. At Smirk, those efforts come together to build something truly unique: a healthcare experience unlike anything traditional insurance has offered before.”
Backed by Fortune 100 CEOs, CHROs, directors, regulators and policymakers.
Leaders who have seen the challenges of the traditional benefits system firsthand and believe there’s a better way.
After leading HR across 100+ markets, it’s clear that portable, personalized benefits are no longer optional, they’re essential for attracting and retaining today’s workforce. Smirk’s infrastructure gives CHROs the tools to help them win the talent war.
Lucien AlziariFormer CHRO, PrudentialI joined Smirk’s board because I believed the health benefits system needed to be rebuilt from the ground up, not patched. For decades, the playbook barely changed, leaving millions of part-time, independent and gig workers without benefits designed for how they actually work. Smirk is building the successor system: portable benefits that follow the person, layered with an AI-powered experience that helps guide people to the right care. That is not an incremental improvement, this is what a new category looks like.
F. Thaddeus ArroyoBoard Director, Smirk Health and Former AT&T Chief Strategy and Development OfficerMy excitement to help Smirk Health resides with helping people struggling with the affordability and quality of health and care.
Dr. Roy Beveridge, MDOncologist, Chief Medical Officer, HumanaSmirk is redefining what economic empowerment looks like for America’s gig and independent workers. By giving people the tools, transparency, and financial access they deserve, Smirk is helping build a stronger, fairer workforce for the next generation of entrepreneurs and creators.
Hon. George P. BushManaging Partner, Pine Cove CapitalData-driven, portable benefits are the next step in total rewards. Smirk’s approach fits global, tech-enabled workforces, clear options, lower friction, and real guidance for employees, with better transparency for employers. By modernizing benefits in this way, organizations can improve retention while giving employees confidence in their choices.
John ClevelandFormer CHRO, Seagate TechnologyAcross my career, I’ve seen how hourly and part-time employees are too often left with benefits systems that don’t meet their needs, and how providers struggle to deliver quality care inside those same constraints. That’s why I’m excited about an unmatched solution that makes access and understanding simple, helps providers schedule and deliver care with ease, and builds highly cost-effective benefits while raising the quality of care. When we design with people in mind and focus on clarity and value, everyone wins.
Michael D’AmbroseFormer CHRO, BoeingWhile health care and drug costs continue to skyrocket, employee benefits have not evolved. Simultaneously gig work and part-time work has become more the norm than the exception. Smirk is creating a novel platform to create affordable solutions for employers and employees. I am excited to partner with Felix and his team to help lower costs and improve outcomes for workers and their employers.
John DriscollFormer EVP and President, Walgreens US HealthcareGetting every American health coverage that is affordable is an undeniable goal. Smirk is achieving this goal for those workers left out of health insurance because of employment and income. Smirk is filling a critical void in our current health care system and has the potential to help millions of uninsured Americans.
Ezekiel J. Emanuel, MD, PhDVice Provost for Global Initiatives, University of PennsylvaniaToday’s organizations with sizable hourly and part-time employees are seeking benefits that are affordable and easy to communicate. Smirk’s benefits programs can fill that need while offering portability to the employees. As workforces continue to evolve, offering contemporary and practical new benefits solutions will further differentiate your value proposition.
Rich FloerschFormer VP and CHRO, McDonald’s, Inc.Health is the most valuable asset we have, and Smirk makes it accessible, flexible, and portable. For companies serious about retention, resilience, and long-term value creation, Smirk offers a future-proof solution that aligns worker wellbeing with enterprise performance.
Daniella FosterSVP & Global Head, Public Affairs, Market Access & Sustainability, BayerThe advent of solutions like Smirk provides a strategic advantage for organizations seeking to offer comprehensive health benefits to their part-time staff. It represents a significant step forward in meeting employee demand while streamlining the administrative burden often associated with traditional plans, a valuable consideration for the right use case.
Michael FraccaroFormer Chief People Officer, MastercardAs a Board Director, Former Chief Human Resource Officer and CPA, I evaluate solutions through strategic, human capital and financial lenses. Smirk’s benefits infrastructure delivers measurable ROI while solving one of corporate America’s most pressing challenges, how to support today’s dynamic workforce.
Harriet HartyFormer CHRO, AllstateCompanies with large numbers of part-time and seasonal employees are consistently searching for solutions to attract the best quality candidates and extend their tenure with the company. Winning demands solutions that are simple to use and easy to deploy. Smirk’s unique platform and portable benefits offering provide employees real value while reducing administrative lift for the business. This drives both efficiency and strengthens workforce stability.
Tim HouriganFormer CHRO, Home DepotSmirk is reimagining health benefits around the realities of today’s workforce, making them more accessible, personalized, and easier for people to understand and use. I’m excited to help advance a model that empowers people to make more confident healthcare decisions.
Sandi KarrmannFormer SVP, CHRO, Kimberly-ClarkThroughout my career, I’ve focused on driving transformation through progressive people strategies, and benefits are a critical part of that equation. Workforces today are more diverse, and fluid than ever before, and benefits must keep pace. Smirk is delivering forward-looking solutions that make benefits more inclusive, portable, and aligned with the way people actually live and work, creating a real competitive advantage for organizations.
Tracy LayneyFormer VP and CHRO, Levi Strauss & Co.Today’s workforce expects flexibility, transparency, and value from their rewards experience. Smirk’s AI-powered wallet delivers on all three, empowering employees with smart, personalized choices while giving employers the insights they need to lead with confidence. It’s a modern solution for a modern Total Rewards strategy.
Kim LupoFormer SVP Total Rewards, GM and WalmartSmirk Health’s AI-powered platform delivers portable benefits to gig workers, part-time employees, and the underemployed, helping employers reduce costs while extending coverage to workforce populations essential for growth and retention.
Suzan Morno-WadeFormer CHRO, XeroxFrom leading HR on the continent of Africa to providing access to education and creating jobs for the homeless and justice impacted, being a solutions-focused and purpose-driven HR leader has been my life’s calling. I linked up with Smirk Health, first as a partner through my company, the R6 Collective, because the alignment was immediate. At R6, we help small businesses, civic organizations, and nonprofits access enterprise-level capabilities without the cost and complexity. Smirk is doing the same in the benefits space: providing access. The need is clear. The timing is right. And the solution is aligned with how the workforce is evolving, so I am honored to support the team in bringing it to market.
Tamla Oates-ForneyFormer EVP, CHRO, USAAThe workforce has seen evolutionary change over the last 100 years. AI will create revolutionary change in just the next few years. Yet the cornerstone of employee benefits, health and wellness, are built on a century’s old model. In order to meet the demands of the future workforce, and the needs of the future employee, there must be a step function change in benefits. Smirk Health is here to address that challenge head on by creating portable and affordable health, dental and vision care for all. Powered by AI and curated to the individual, Smirk Health’s vision will change the landscape of benefits for good.
Kalen PieperFormer EVP, Partner Resources, StarbucksThe gig economy is a cornerstone of the modern workforce, yet the benefit needs of these workers remain largely unmet. Smirk addresses this gap by providing tailored benefit solutions for this tech-enabled workforce. Utilizing AI guidance and transparent pricing, they offer next-generation solutions for the next-generation workforce.
Susan PodlogarFormer CHRO, MetLifeSmirk is forward-thinking in the way it addresses the challenges of today’s workforce and the future of benefits, building a model that is more human, personalized, and aligned to how people actually live and work.
Gisel RuizFormer COO/EVP, Walmart U.S. & Sam’s ClubWe are in the midst of an extraordinary movement redefining both how work gets done and how people work. Smirk Health is poised to be an integral part of this transformation, enabling individuals to access quality, affordable healthcare benefits that are truly portable. At the same time, Smirk empowers companies to rapidly evolve their approach to benefits, meeting significant cost pressures head-on while responding to the evolving needs and expectations of a modern, dynamic workforce.
Ellyn ShookFormer CHRO, AccentureSmirk is solving one of the biggest challenges in healthcare, providing affordable coverage for medical, dental and other benefits for working people who do not qualify for traditional, employer sponsored insurance and can’t afford ACA plan premiums. And Smirk is building these affordable benefits to deliver real value for their enrollees, by helping enrollees find and access affordable care, and providing flexible benefit options that enable enrollees to tailor their benefits to their needs and take them with them even if they change employers.
Dr. Glen Stettin, MDFormer Chief Innovation Officer, EvernorthThe workforce is evolving faster than traditional systems can keep up, and Smirk is building the new infrastructure layer for health benefits; bespoke, portable, preventive-first, and designed for how people actually live and work today.
Harit TalwarFormer Chairman, Goldman Sachs Consumer Business GroupThe benefits system in this country was built for a workforce that barely exists anymore. Most startups in this industry get stopped before they can even start because of the regulatory complexity. We’re proud to have invested in Smirk and to work alongside Felix and his team as they disrupt the status quo and get people the care they need.
Bradley TuskFounder & CEO, Tusk HoldingsAs work shifts toward independent and gig-based models, traditional employer-sponsored benefits are becoming obsolete. Companies are moving to flexible, packaged platforms that match how people work today. Smirk leads this shift with a scalable, AI-driven platform that delivers choice, portability, and affordability, redefining access and value for the modern workforce.
Brent WilliamsFormer Founder and CEO, Dental SelectBuild your benefits. Own your benefits. Use your benefits.
Finally.Mobile Health Benefits built for today’s workforce.