employee-benefits
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Tammy Sun and the Business of Getting to Yes
Before Tammy Sun built Carrot into a global benefits platform, she learned to read institutions from the inside. Her career is a study in what happens when a founder trusts the customer’s yes more than the market’s no.
Mathew Augustine Has Spent a Career Making Small Employers Feel Bigger
From the outsourcing boom to construction payroll, Augustine keeps returning to one stubborn problem: how can a smaller employer offer the care, clarity and infrastructure of a much larger one?
Jonathan Asmis Is Turning the Down Payment Into a Talent Strategy
The Landed co-founder spent a decade testing a stubborn idea: when capable workers cannot afford to live near their jobs, better financial plumbing can do more than another perk.
Laurel Taylor Is Turning Student Debt Into a Workplace Design Problem
She borrowed her way from a small Texas town to MIT and Google. Then she spent a decade redesigning the benefit she and her mother needed: a way to pay down debt while life keeps compounding.
Joseph Kitonga Put a Healthcare Idea in a Mall Kiosk - Then Took It Nationwide
A family business exposed the gap. A $10,000 student prize funded the first attempt. Joseph Kitonga built Vitable by meeting workers face to face, then kept widening the map.
Quan Nguyen Is Building a Payday That Arrives When the Work Does
The former banker left a comfortable finance career to rethink the long wait between earning money and receiving it. At Gimo, his wager is that a fairer payday can become the front door to wider financial access for Vietnam’s workers.
Amr Yussif Turned a Missing Paycheck Into a Fintech Thesis
A withheld gratuity sent the Dubai finance executive to a government queue before breakfast. What he saw there became FinFlx - and a practical lesson in building from the liability nobody wants to discuss.
Mahima Chawla Turned Leave’s Paper Chase Into a Product People Could Trust
A colleague’s laptop-at-the-hospital story sent Mahima Chawla into the unlovely machinery of employee leave. Six years, 25,000-plus leaves and one acquisition later, her career offers a quiet lesson in building software for the moments when paperwork feels most personal.
Carey Cook Took the Long Road to the High Road
After 28 years shaping student life, an Idaho educator traded the campus office for payroll, benefits and workers' comp - then merged his young company into a larger regional platform without giving up its local brief.
The Backup Plan That Became the Business
Sharon Lurtsema spent decades learning what happens when care falls apart. Then she built a company around making the backup plan feel less like a scramble - and more like infrastructure.
Alok Deshpande Built a Money Classroom for the Middle Class
He left Bain, invited six Atlantans into a room, and taught the least glamorous lesson in money: spend less than you make. Fifteen years later, that stubbornly simple idea is becoming software without losing the teacher inside it.
Cesar Carvalho Kept the Problem and Fired the Product
He left Harvard with a gym-pass idea. Fourteen years, several pivots and one abandoned brand later, Cesar Carvalho has built his career around a rarer discipline: loyalty to the problem, not the first answer.
Seif Saghri Built a Perks Company Before Perks Became a Strategy
In 1999, employee perks were often a homemade list of deals. Seif Saghri turned that neglected HR chore into an online marketplace, spent 25 years widening its reach, then learned the founder’s last operating lesson: how to hand over the keys.
Priyang Shah Found a $10,000 Hole in Employee Benefits
After helping scale two Columbus startups, Priyang Shah returned to a stubborn piece of household math. His answer became Healia - and a case study in building ambitious software from Ohio.
Joli Kindler Built a Brand Inside the Quietest Corner of Finance
A marketing coordinator who never left, and spent fifteen years turning insurance brokerage into a brand people could actually feel.
Amy Spurling
After three tours as a CFO, Amy Spurling stopped treating employee perks as a shopping list. Compt is her attempt to turn a stubborn budget line into a system built on choice, evidence, and trust.
Guy Benjamin
Guy Benjamin is the CEO and co-founder of Healthee, a New York-based company that uses AI to help employees understand and use their health benefits. A former Israeli Air Force fighter pilot with a Yale MBA and a McKinsey background, he started Healthee in 2021 after struggling to navigate his own employer benefits in the US. The company has grown past 15,000 customers, counts Instacart, SiriusXM, and Celonis among its clients, and has raised $111 million in total funding, including a $50 million Series B in 2025.
Guy Ezekiel
Guy Ezekiel is the co-founder and CEO of Zorro, an AI-powered ICHRA benefits platform that helps employers replace one-size-fits-all group health plans with personalized, individual coverage. A 25-year healthcare operator turned venture investor, he spent much of his career building medical device and pharmaceutical companies before becoming a managing partner at Pitango, Israel's largest VC fund. He left investing to co-found Zorro in 2022 with Maya Perl, betting that Individual Coverage Health Reimbursement Arrangements will do for health benefits what the 401(k) did for retirement. Zorro has raised $31.5 million to date, including a $20 million Series A in June 2025.
Matt Watson
Matt Watson is the co-founder and CEO of Origin, a Boston-based fintech that in September 2025 launched what it calls the first SEC-regulated AI financial advisor. A former Citigroup high-yield credit trader who previously co-founded Indio Technologies (acquired by Applied Systems in 2019), Watson has raised more than $75 million for Origin from Founders Fund, Felicis, General Catalyst and 01A to make certified-financial-planner-quality advice available to people who normally can't afford it.
Nick Abramovich
Nick Abramovich is the CEO of Workers Benefit Fund, a New York-based benefits platform that builds the plumbing between gig workers, freelancers, independent contractors and the government, union and private benefits they are eligible for but almost never enroll in. He has been running the company since 2019, when WBF acquired BeneStream, the Medicaid-for-the-workplace outfit he ran as President. Under him, WBF added Upward Finance in December 2024, extending the platform from healthcare enrollment into tax and earnings tools for gig workers. Before benefits, he was CEO of Synaptic Digital and CMO of Ditech Holding Corporation, with earlier stops at MetLife, MoveOnIn.com, and BizSlate. Columbia MBA, Tulane BS.
Pauline Roteta
Pauline Roteta is the co-founder and CEO of Pasito, a New York based startup building AI agents for the insurance and employee benefits industry. A former Senior Investor and Portfolio Manager at BlackRock, Fulbright Scholar, CFA and CFP, she launched Pasito in 2021 to attack the roughly $200 billion Americans waste each year on poor benefits decisions. Pasito went through Y Combinator's Summer 2022 batch and in February 2026 raised a $21 million Series A led by Insight Partners, bringing total funding to about $24.4 million.
Justin Holland
Justin Holland is the co-founder and CEO of HealthJoy, a Chicago-based digital health company that turns the maze of employee benefits into a single AI-guided app. An MIT-trained engineer and serial entrepreneur with two prior exits (OpenInstall to AVG/Avast and FreeCause to Rakuten), he started HealthJoy in 2014 after a personal run-in with the American healthcare system left him unable to find out what his own care would cost. He has led the company for more than a decade, raised roughly $108M in venture financing through a Series D, and built a platform now used by hundreds of thousands of members to navigate care, cut costs, and reach a virtual assistant named JOY.
Jon Cooper
Jon Cooper is the Co-founder and CEO of Overalls, a New York-based insurtech startup that pairs AI-augmented human concierge specialists with employees to handle life's logistics - from childcare coordination to medical billing to passport renewals. A serial entrepreneur who previously built and sold Life.io to Zinnia, Cooper brings 15+ years of insurance and healthcare strategy experience to Overalls, which was named to Fast Company's World's Most Innovative Companies of 2026. The company has raised $15.8M in funding and serves employers seeking to reduce employee stress and boost productivity through its LifeConcierge product.
George Fatheree
George Fatheree is the founder and CEO of Oro, a Los Angeles public benefit corporation that brings housing support into the workplace as an employee benefit. A former Big Law real estate partner at Sidley Austin, Munger Tolles & Olson and Skadden, he is best known for engineering the historic return of Bruce's Beach to the Bruce family in 2022, the first time in U.S. history that land seized through racially motivated eminent domain was returned to a Black family. He now applies the same financial and legal machinery to closing the wealth gap at scale, raising $3 million in early 2026 to launch Oro's housing wellness platform.
Rachel Schneider
Rachel Schneider is the founder and CEO of Canary, a New York fintech that lets employers and donors give tax-free emergency cash grants to workers in crisis. Before building software, she spent years studying how American families actually handle money - co-authoring the acclaimed book The Financial Diaries with economist Jonathan Morduch - and held senior roles at Merrill Lynch, the Aspen Institute, and the Financial Health Network. Canary turned that research into a product: a confidential application that moves money to people at the moment they need it most.
Shannon Goggin
Shannon Goggin is the co-founder and CEO of Noyo, an API-first company building modern data infrastructure for the employee benefits industry. After watching benefits data break down behind the scenes at Zenefits, she and co-founder Dennis Lee launched Noyo in 2017 to fix the plumbing that connects insurance carriers, benefits platforms, and the people who depend on accurate coverage. She has raised more than $57 million for the company, was named to the Forbes 30 Under 30 list in 2020, and calls her approach 'collaborative disruption' - rebuilding an entrenched industry by understanding it rather than ignoring it.
Alison Richards
Alison Richards is the CEO of Surest, a UnitedHealthcare company (formerly Bind) that builds a health plan with no deductibles and upfront prices people can see before they book care. A UnitedHealthcare veteran since 2012, she has turned the company's most contrarian benefits idea - let members shop for care the way they shop for everything else - into its fastest-growing employer plan.
Vivek Shah
Vivek Shah is the co-founder and CEO of SimplyInsured, a San Francisco company that lets small businesses compare and buy employee health insurance entirely online - billed as 'Kayak for health insurance.' An MIT-trained engineer and former McKinsey healthcare analyst, he started the company in 2012 after a maddening personal experience trying to buy coverage. Backed by Y Combinator (W13), Bessemer, and Polaris, SimplyInsured has served roughly 25,000 small businesses and saved them more than $50 million.
Jeff Schneble
Jeff Schneble is the CEO of Human Interest, a San Francisco-based fintech company on a mission to close America's $28 trillion retirement savings gap by making 401(k) and 403(b) plans affordable and accessible for small and medium-sized businesses. A physicist turned venture capitalist turned operator, Schneble brought together a rare trifecta of academic rigor (PhD from Cambridge, MBA from Harvard), investment experience (Partner at Wing Venture Capital), and hands-on operational chops (Silver Lake Partners) before taking the helm at Human Interest in 2019. Under his leadership, the company has grown to serve over 45,000 companies, surpassed $200 million in ARR, raised over $1 billion in total funding at a $3 billion valuation, and is eyeing a public listing.
Matt Levin
Matt Levin is the CEO of Modern Health, a leading global workplace mental health platform. A serial CEO with two decades of leadership across HR technology, health care, and benefits, Levin has helmed Benefitfocus (sold to Voya Financial), People 2.0 (a 50-country HR platform), and held C-suite roles at ADP and Aon. He was part of the core team that engineered the landmark $4.9 billion Aon-Hewitt merger and was recognized as a World Economic Forum Young Global Leader in 2013. A Chicago-based operator and longtime lecturer at both Northwestern and the University of Chicago, he now leads Modern Health's mission to bring proactive, globally equitable mental health care to the world's workforce.