Kaiza Molina is the Co-Founder and Chief Operating Officer (COO) of StretchDollar, a San Francisco-based, venture-backed health technology company transforming how small and medium-sized businesses deliver modern, affordable health benefits.
Recognized as a “Female Disruptor” in health tech and one of the most knowledgeable voices on Individual Coverage Health Reimbursement Arrangements (ICHRAs), Kaiza is expanding access to healthcare through bold thinking, real-world execution, and principled leadership. Today, she has been named an honoree of Inc.’s Female Founders 500, a prestigious list recognizing the most creative and inspiring female leaders in America.
Her work has been featured in leading national publications including TechCrunch, Fierce Healthcare, Business Insider, Bold Journey, and WomLEAD, and on prominent podcasts such as InsHER and Latinas in Tech. She has also been invited to speak at the Stanford Graduate School of Business, sharing insights on entrepreneurship and the future of health benefits.
Backed by top-tier investors including Oscar Health, StretchDollar has been recognized as one of the Top 50 Global Insurtechs in the Health & Benefits category, reflecting the company’s rapid momentum and Kaiza’s strategic vision.
With an operational foundation shaped by her work at Gusto, a leading payroll and benefits technology company, and Decent, an innovative health insurance startup, Kaiza brings a rare combination of intellectual rigor, operational excellence, and founder-level grit to building and scaling companies in complex, highly regulated industries.
Born and raised in San Francisco, California, Kaiza is a proud graduate of Chapman University, where she earned a Bachelor of Science in Business Administration. Today, she stands among the defining leaders of the insurtech movement as one of the few Latina co-founders in an industry where fewer than 12% of venture dollars go to women—and even fewer to Latinas. Kaiza has proven to be the exception, not the rule.
Through fearless leadership, she is breaking barriers across healthcare and technology, setting a new standard for what is possible while serving as a powerful role model for the next generation of women and underrepresented founders.
Kaiza Molina is not only building a company—she is helping reshape the U.S. healthcare system by delivering scalable, human-centered benefits solutions for the small and mid-sized businesses that have long been underserved.
Her presence is commanding.
Her leadership, unapologetic.
Her mission, unwavering.
Her execution? Relentless.
“I believe every business, no matter the size, deserves access to better care and smarter benefits.”
— Kaiza Molina
Kaiza Molina
Co-Founder & COO, StretchDollar
Inc. Female Founders 500 Honoree
Fearless leader redefining access to smarter, human-centered health benefits.
Press & Media
Featured in top business and healthcare publications highlighting Kaiza Molina’s leadership in insurtech, innovative startup growth, and her work as co-founder and COO at StretchDollar.
Named among the Top 50 Global Insurtechs in the Health & Benefits category.
Co-funder and COO of StretchDollar, redefining how SMBs deliver health benefits.
Profiled for transforming SMB access to modern, human-centered health benefits.
Recognized as a female disruptor and advocate for inclusive entrepreneurship.
Featured for her leadership in redefining how SMBs deliver health benefits through ICHRA innovation.
Interviewed on leadership, resilience, and the future of women in tech.
Podcasts
Kaiza Molina, Co-founder and COO of StretchDollar, shares how accessible health care starts with simplicity, empathy, and systems designed around how people actually make decisions.
Let’s Work Together
Kaiza Molina is a people-first leader who believes confidence sparks possibility and uniqueness creates advantage.
Her philosophy is simple: “If you’re even thinking about starting a business—do it. Failure isn’t the enemy; regret is. Every setback is a lesson, every “no” a new path forward, and every stumble a step closer to your full potential.”
She helps founders, executives, and teams navigate inflection points, lead through complexity, embrace failure as fuel and shift their mindset to unlock their next level of growth and success.
As one of the few Latina co-founders in insurtech, Kaiza is deeply committed to helping women and underrepresented leaders claim their voice, own their power, and lead with unapologetic purpose.
Founders don’t need more noise, they need someone who’s been in the seat. Kaiza’s years of experience and proven track record make her a trusted advisor. Her fearless leadership challenges others to lead boldly.
Ready to think bigger? Work with Kaiza:
Executive and founder consultations
Keynotes, panels, and fireside chats
Strategic and operational advising
Leadership coaching and mentorship for women and Latina founders