Felix W. Ortiz III is a serial entrepreneur passionate about expanding access and opportunity through innovation. A U.S. Army veteran who served in the JAG Corps and 18th Airborne Corps, Felix combines disciplined leadership with a deep commitment to creating solutions that improve people’s lives at scale. As the CEO of Smirk Health, his mission is deeply personal. Watching his parents navigate the complexities of insurance while caring for his brother’s heart condition showed him how broken and inaccessible the healthcare system can be for families. That experience continues to drive his work to make healthcare more affordable, transparent, and human-centered for everyone. Outside of work, Felix is an avid runner who has completed four of the seven World Marathon Majors and continues to train for the remaining three.
The healthcare ecosystem is broken — we’re building the one the workforce and employers deserve.
Smirk Health is creating a new category in healthcare benefits — the Benefits Infrastructure Layer that powers the Smirk Wallet™. A modern, AI-powered platform that removes the friction and hassle of healthcare while unlocking access through portable, modular coverage that follows the worker — breaking through outdated, employer-tied systems to give people real control over their care.
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Developing the future of health benefits together.
The health benefits system wasn’t built for today’s workforce — or the employers striving to support them. At Smirk, we’re creating the first Benefits Infrastructure Layer, a smarter, portable platform that meets workers where they are and helps organizations lead with confidence.
Designed with F100 CHROs and top medical experts who share our vision, Smirk sets a new standard where transparency, flexibility, and support are a right—not a perk. Coverage is underwritten and insured by Chubb, a trusted global carrier.
Today's health benefits are stuck in the last century.
The U.S. benefits infrastructure was designed in 1929, almost 100 years ago, for full-time employees. In today’s new era of work, millions of contractors, part-timers, retirees and gig workers are left exposed to rising premiums, shrinking Affordable Care Act subsidies and trapped in costly one-size-fits-none plans while employers absorb higher costs and constant turnover trying to compete for talent in a fractured market.
Smirk designed a new path:
The benefits infrastructure layer for the modern workforce
Benefits that move, predict, guide and care.
Traditional brokers and marketplaces tinker at the edges of a system built for another era. Smirk is carving out a new category: The Benefits Infrastructure Layer — accessible, adaptable, portable, and truly human-centered.
We put people back at the heart of care and retire the rigid, one-size-fits-none model.
Dan
Dan Hunter is an accomplished healthcare and technology operator with over two decades of leadership experience. He co-founded Smirk Health and is pioneering a digital-first approach to dental insurance. Previously, he was an early executive at SmileDirectClub, leading revenue cycle operations and international back-office expansion through its $8.9B IPO. Dan has also held leadership roles at DaVita and Simplex Healthcare.
Elad Shaham is a seasoned technology leader with more than 20 years of experience scaling engineering organizations. He has held leadership roles at Lemonade, PayPal, and BillGuard, specializing in FinTech and consumer platforms. At Lemonade, he helped grow the engineering team tenfold and modernized its architecture. Today, he applies his expertise in early-stage growth to build and scale Smirk Health’s technology foundation.
Micah
Micah Alpern is a design and product leader based in Mountain View, CA. He’s led design at Instacart and Venmo, guiding product vision and execution while growing strong design teams. Earlier at Facebook, LinkedIn, and eBay, he worked on products that reach people around the world every day. His work combines design craft, clear strategy, and practical execution to create products that work well and feel right to use.
Alex Carstens is a two-time VC-backed founder and angel investorwith expertise in finance, technology, and social enterprise. He began his career in investment banking and private equity before co-founding ventures like Viridis and KarmaBox. A Columbia Business School MBA, he has also led social impact investments at the LEO Impact Fund. At Smirk Health, Alex oversees strategy and finance, driving innovation and growth.
Melissa Stefani-Bolin is a brand strategist and marketing leader who drives growth across healthcare, technology, and culture-powered brands. At Smirk Health, she leads brand and marketing, championing its category-defining mission to put the patient back at the centerof the healthcare ecosystem and make benefits truly human and accessible. She’s fueled growth and transformation for health systems, AI/AR startups, deep tech, and Fortune 500 giants. Melissa partners with executives to spark brand evolution, craft new categories, and ignite audience engagement with fearless creativity and measurable impact.
Sam joined Lemonade in 2018, driving strategic partnerships and holding multiple growth roles through their IPO and beyond. She worked across all of Lemonade’s insurance products—from home to life, pet and car—leading initiatives in partnerships, paid media, and new product launches. Sam built, executed, and owned the P&L for Lemonade Car, taking it from zero to multi-million ARR. Since then, she’s brought her insurtech expertise to Assured Allies and Fairmatic, advising on growth strategy and performance marketing across longevity and commercial auto insurance.
Backed by visionary enterprises, operators and regulatory advisors
“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.”
Guided by the best minds in benefits and care.
Smirk is built in collaboration with leaders who understand every layer of the benefits puzzle — from plan design and employee experience to modern, intelligent technology.
F100 CHROs and the top medical advisors bring deep expertise to shape a platform that’s practical for employers, builds workforce confidence and evolves with the future of healthcare.
Endorsed by world-class medical advisors.
Ezekiel J. Emanuel, MD, PhD, is the Vice Provost for Global Initiatives and the Diane v.S. & Robert M. Levy University Professor at the University of Pennsylvania.
An oncologist and one of the world’s most cited scholars in health policy and bioethics, he founded and chaired the Department of Bioethics at the National Institutes of Health and was a principal architect of the Affordable Care Act while serving as Special Advisor on Health Policy to the White House. Dr. Emanuel advises the Director-General of the World Health Organization, is a Senior Fellow at the Center for American Progress, and serves on the Council on Foreign Relations.
He is the author or editor of 15 books and 350+ publications, a Guggenheim Fellow, and an elected member of the National Academy of Medicine and the American Academy of Arts & Sciences.
Dr. Emanuel brings unmatched experience and insight to Smirk’s mission to modernize health benefits and put workers and employers at the center of care.
Dr. Roy Beveridge is a medical oncologist who has been in practice for more than 25 years. He served as Humana’s Chief Medical Officer for seven years where he led clinical policy, population health, clinical compliance and clinical quality initiatives for both medicine and dentistry. He has held similar roles for US Oncology and McKesson specialty. Much of his recent work has focused on value based medicine and improving the health of underserved populations. “My excitement to help Smirk Health resides with helping people struggling with the affordability and quality of health and dental care.”
Underwritten and insured by
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.