The new era of work fuels the next era of health benefits.
Smirk breaks through the outdated benefits maze — unlocking access to portable, affordable, modular coverage that moves with you. One wallet connects your insurance, care management, transparent pricing, and personalized AI guidance so you can get the right care for your needs — easily, clearly, and confidently.
Not another flimsy card lost in a drawer. Smirk removes the friction, putting everything in one place and powered by your AI personal concierge — built to match your needs, guide your choices, and keep your care moving forward. This is healthcare the way it should be: simple, personal, and built around you.
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Underwritten and insured by
Helping you cut through the healthcare benefits chaos.
Smirk is putting people and access to healthcare first.
Traditional benefits were built around outdated insurance models created almost a hundred years ago — leaving employers overspending and employees juggling plans that don’t fit the realities of today's workforce.
For employers, Smirk delivers actionable insight into utilization, boosts engagement, reduces churn, and turns benefit waste into value. With rolling enrollment, AI-powered employer dashboards (utilization, adoption, churn), and low-lift HCM integrations, you cut complexity without adding vendors or admin lift.
For employees, we make care simple: portable coverage in the Smirk Wallet and your AI personal health concierge that gets to know you and helps manage everything from appointments to prescriptions.
Underwritten and insured by Chubb, a partner known for high-quality and excellent service, Smirk is unlocking benefits that are accessible, flexible, transparent, and designed for today's workforce.
The only system that manages your health, not just your insurance benefits.
Smirk unlocks access to affordable, portable benefits — with clear pricing, predictive guidance, and AI driven, smart personalization — transforming healthcare into a transparent, seamless experience. Part-time, gig, seasonal, retired or gap—Smirk goes where you go.
Portable coverage that moves with you.
Nationwide access.
Affordable protection.
Smirk Wallet + Health Concierge.
Transparent costs.
Fast, flexible enrollment.
Superior coverage for the workers traditional benefits leave behind.
One wallet. Total clarity. Complete portability.
The Smirk Wallet™ enables access and true portability for the workers traditional benefits have forgotten — protection that moves with you from job to job, gig to gig, and stage to stage. All your healthcare benefits. One trusted place.
Easily schedule appointments, find a provider near you, and manage care visits all in one place.
Get friendly reminders and updates that help you keep up with your care — so nothing slips through the cracks.
See estimated costs before your visit and get helpful reminders to stay on top of your personalized care.
Your coverage moves with you, across employers, platforms, and life changes.
Pay, track, and manage benefits — zero friction, no confusion.
Say hello to Ailene™, your personal AI care concierge.
Support that's customized just for you. Ailene™, your personal AI health concierge lives in your Smirk Wallet™, guiding you through care and keeping you on track. Book appointments, refill prescriptions, get reminders, and stay ahead on next steps — so healthcare isn’t another thing on your to-do list.
Book care in seconds
From dental cleanings to doctor visits, Ailene™ makes it easy to find providers, schedule visits, and stay on top of your care — no portals or long wait times.
Stay ahead of your care
Ailene™ surfaces next-best steps, appointment nudges, and follow-ups tailored to each member — keeping care simple and connected.
See cost estimates upfront
Ailene™ surfaces estimated costs and coverage details before you book, helping you plan ahead with confidence.
Cut through the healthcare chaos.
Enroll through your employer or directly on our dental plan page. Your benefits kick in as soon as your coverage is active.
Smirk Wallet™ + Ailene™ help you personalize your benefits — dental now, with medical coming soon — recommending plans, surfacing savings, and making setup effortless.
Your Smirk Wallet™ keeps coverage continuous across your personal journey — with AI-powered guidance, clear costs, and smart insurance that works for you.
Coverage that keeps you grinning
Get covered in minutes. Smirk is blowing up outdated dental plans. No flimsy cards. No fine print. No confusion.
From cleanings to big fixes — Smirk brings clarity, simplicity, and real support, all managed in your personal Smirk Wallet™.
No waiting periods once you’re effective. And with coverage underwritten and insured by Chubb — a name trusted for quality and service — you get benefits you can actually rely on. The old way is over. This is personalized healthcare without the chaos.
Plan start at less than $1.60/day for dental insurance.
That's less than a cup of coffee.
Coverage that keeps you grinning
Get covered in minutes. Smirk’s proprietary dental plans, designed with Chubb, offer transparent pricing and a broad network for everything from cleanings to major procedures — all managed in your Smirk Wallet. Insurance coverage begins on the first of the following month.
Plans start at less than $1.60/day for dental insurance. That’s less than your daily matcha.
Future-ready, frictionless benefits for the modern workforce.
Smirk builds benefits around people — blending insurance, AI-powered insights, and intuitive tech to boost retention, attract talent, and give employers visibility and ROI, while employees get personalized care that fits real life.
Traditional benefits
Smirk unlock
Expand health benefits. Strengthen retention.
Smirk gives employers a turnkey way to unlock affordable, portable coverage for non-traditional workers — part-time, 1099, gig, gap periods and seasonal — without friction. AI-powered insights help reduce spend, boost retention and acquisition, and free HR from admin work.
Backed by world-renowned F100 CHROs and top medical experts.
“The gig economy drives today’s workforce, yet workers’ benefit needs remain unmet. Smirk fills the gap with tailored, AI-guided, transparent solutions—next-gen benefits for the next-gen workforce.”
“Companies 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.”
“Today’s workforce expects flexibility, transparency, and value. Smirk’s AI-powered wallet delivers personalized choices for employees and actionable insights for employers—a modern solution for Total Rewards.”
“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.”
“As a Board Director, former CHRO, and CPA, I assess solutions through strategic, human capital, and financial lenses. Smirk delivers measurable ROI while solving one of corporate America’s biggest challenges, supporting today’s dynamic workforce.”
“Across 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.”
“Smirk 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.”
As a former CHRO with a strength in employee Total Rewards I encountered many underserved team members that were key to our growth and success who were not eligible for company benefits. Smirk provides the solution. Whether the team member is a Contractor, GIG Employee, Part Time or a Retiree Smirk is there to support them in their health and welfare needs that they can take with them!
“Getting 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. What a noble and important goal.”
“My excitement to help Smirk Health resides with helping people struggling with the affordability and quality of health and dental care.”
“Smirk gives organizations a strategic edge by offering comprehensive benefits for part-time staff, meeting employee demand while easing the admin burden of traditional plans.”
“Today’s diverse, fluid workforce demands benefits that keep pace. Smirk delivers inclusive, portable, forward-looking solutions that align with how people live and work—giving organizations a true competitive edge.”
“Today’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.”
“Health is our most valuable asset, and Smirk makes it accessible, flexible, and portable. For companies focused on retention and long-term value, Smirk aligns worker wellbeing with enterprise performance.”
“While 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.”
“As 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.”
A game changer for employers.
Set cohorts, define coverage levels, and get enrollment ready in weeks — no new systems or heavy lifts required. Smirk integrates with your existing HCM to make setup simple and seamless.
Flip the switch and go live fast. Automated compliance, plug-and-play workflows, and zero extra headcount mean no vendor sprawl and no long ramp-up. Just benefits that work from day one.
Smirk’s Employer Dashboard delivers real-time, AI-powered insights on utilization, engagement, and retention — giving you the clarity to prove impact, control spend, and make informed decisions, fast.
The hassle-free way to next-gen healthcare benefits.
Lead the new era of workforce benefits.
Traditional benefits weren’t built for today’s workforce. Smirk fuses insurance, AI, and hands-on guidance into one simple system — cutting admin time for employers and giving employees flexible, personalized coverage and clarity.
A system that works for today's non-traditional workforce.
Smirk helps companies cut spend and keep talent — while giving every worker clear, portable coverage. Join employers rethinking how health benefits are delivered today.