The Bakery Problem That Built a Company
There is a moment Samad Wahedi keeps coming back to. Not a pitch meeting, not a fundraise announcement, but a kitchen table conversation with a family member who runs a small business. The coverage was wrong. The price was too high. The broker didn't understand the business. The technology was so old it didn't even have a website worth using. Wahedi recognized the absurdity. He had spent years inside the machinery of early internet companies - helping build InsWeb as it went public, steering Velosel to a $40M raise before TIBCO acquired it, founding and selling DirectQuality. He knew software. He knew insurance. He knew the gap between them was colossal.
In 2018, he launched Glow. Not with a deck full of AI buzzwords, but with a specific conviction: small businesses - the bakeries, the cleaning crews, the contractors - were absorbing a disproportionate burden from an industry designed for corporate clients. They were overpaying. They were underprotected. And nobody with real technology talent was bothering to fix it.
Six years later, Glow has 280 employees, $41.5 million in total funding, and a platform that links directly to payroll to deliver workers' compensation insurance that adjusts in real time. When you hire someone, your coverage updates. When you let someone go, your premium moves accordingly. No forms. No lag. No end-of-year audit surprises.
If you're a small bakery, you want to know that your employees and your assets are safe - but your focus is baking. At the same time, insurance comes out of your margins. Overpaying can mean a lot of cupcakes.
- SAMAD WAHEDI, FOUNDER & CEO, GLOWThat particular sentence - "overpaying can mean a lot of cupcakes" - is Wahedi at his most precise. He doesn't talk about market disruption. He talks about a bakery owner whose focus should be on the bread. That shift in framing - from macro to granular, from industry to individual - is how Glow has been built from the inside out.
Led by Cota Capital, Nov. 2022
U.S. small business insurance
Software & insurance tech
Founded or led before Glow
Twenty-Five Years Before Glow
Wahedi's career reads like a training manual for building Glow. Each chapter added a layer: engineering rigor, quality discipline, executive experience at scale, the particular madness of founding something from scratch, twice.
The InsWeb chapter deserves a closer look. Working at a company bringing insurance to the web during the dot-com era - and watching it go public - gave Wahedi a front-row view of what digital distribution could do to an entrenched industry. It also gave him a preview of how resistant that industry could be. He spent the next 17 years in enterprise software, and came back to insurance in 2018 with both patience and precision.
What Glow Actually Does - and Why It's Harder Than It Sounds
Workers' compensation insurance is the entry point. Every business with employees needs it. Most businesses hate dealing with it. The traditional process involves an agent who may or may not understand your industry, a carrier who prices based on broad job categories rather than actual risk, and an annual audit that can hit you with a surprise bill months after the fact.
Glow replaces this with a data-driven pipeline. The platform connects to your payroll system - getting a real-time read on your workforce - and uses that data to match you with the carrier that fits your specific risk profile. Coverage updates automatically as your team changes. No audit surprises. No mid-year scrambles. And the savings from more accurate risk assessment, the company claims, average 20% or more versus traditional alternatives.
Our goal is to take care of all small business insurance needs, because insurance provides the peace of mind to pursue your dreams.
- SAMAD WAHEDIBeyond workers' comp, Glow has expanded into business interruption insurance, property and casualty, and other commercial lines. The long game is to become the single insurance relationship for a small business owner - not a price-comparison site, but a dedicated advisor that actually knows your business and adjusts coverage as it grows.
The platform also extends coverage to accidents outside work hours - what Glow calls "Accident Benefits" - without raising premiums. It's a detail that sounds incremental but signals something larger: Wahedi is building toward a version of small business insurance that actually cares about the people it covers, not just the employers writing the checks.
Key Moments
Be Unreasonable. Go All In. Trust Your Gut.
Wahedi does not talk like someone who has been through media training. His framework for operating - as shared with AV8 Ventures - is direct to the point of being almost blunt.
Three rules surface consistently. First: be unreasonable. Progress, in his view, belongs to people who refuse to adapt themselves to the world and instead insist on the reverse. Second: go all in. He uses the phrase "burn your boats" - the Cortez image of destroying the ships so retreat is impossible. Commitment without a safety net, by design. Third: trust your intuition. He is specific about this. Ignoring his gut has, in his experience, consistently led to poor decisions. The lesson has become operational.
On hiring, Wahedi is equally direct. Technical skills matter, but cultural fit comes first. He is looking for people who want to be in a demanding startup environment, not people who can tolerate it. The distinction is meaningful: one is a choice, the other is endurance.
What He Has Built
- Founded Glow in 2018 and grew it to 280 employees and $41.5M in total funding within six years
- Led Glow's $22.5M Series A in November 2022 - the largest single raise in the company's history
- Built a payroll-integrated insurance model that eliminates annual audit surprises for small businesses
- Previously helped build InsWeb, one of the first online auto-insurance marketplaces, through its IPO
- Founded and sold DirectQuality within three years
- Worked at Velosel through a $40M+ venture capital raise and subsequent sale to TIBCO
- Expanded Glow from a California workers' comp specialist into a multi-state, multi-line commercial insurance platform
- Backed by Cota Capital, AV8 Ventures, Maiden Re, Markd, and Startup Venture Capital
The Specifics
His LinkedIn handle is simply "wahedi" - no numbers, no underscores, no qualifiers. That's old Silicon Valley.
His first insurance experience was at InsWeb during the dot-com boom in 2000. He has spent 25 years circling back to finish the job.
Currently reading "Amp It Up" by Frank Slootman - a book about scaling companies through hypergrowth. A signal of what he expects to be doing soon.
Glow's payroll sync means insurance costs adjust automatically as businesses hire or lose workers. No monthly paperwork. No surprises at audit.
Glow's "Accident Benefits" extend coverage outside work hours without raising premiums - a structural choice that costs money but signals intent.
Before becoming a founder, Wahedi built his career in software quality assurance. He spent years ensuring things work before shipping. It shows in how he runs Glow.
How He Operates
Wahedi values systems thinking and complex problem-solving over isolated feature work. He chose insurance not because it was fashionable - insurtech had its moment and lost it - but because fixing it has real human consequences. His family members were affected. People he knows are affected. That's not a pitch. That's a constraint he built around.
On investors, he's particular: mutual respect and trust before term sheets. He describes the ideal investor relationship as a partnership, not a transaction. Given that Cota Capital, AV8 Ventures, and Maiden Re are among his backers, the approach appears to be working.