Yousuf Khan has bought enterprise software as CIO at companies including Pure Storage, Moveworks, and Qualys. He funded enterprise startups as a partner at Ridge Ventures. And now, as founder and CEO of Clario, he’s building one himself.

He joins Shuly Galili on Runtime to unpack what he learned from each seat: why a CIO decides in the first five minutes whether a startup is building something of consequence, why the security team belongs in the second meeting, and why he became an early Zoom customer in 2015—even when people laughed at the idea.

For years, Yousuf was, in his words, “the weirdo in the Bay Area.” Now he’s the one pitching.

Clario—which he calls “the Marie Kondo of enterprise data”—raised a $6 million seed round, and Yousuf is now selling to the same CIOs he still brings together for “group therapy” dinners three times a month.

A candid conversation about enterprise buying, selling, investing, and what founders often misunderstand about the CIO on the other side of the table.

New episodes every other Wednesday.

Produced by POLDHU.

CHAPTERS

00:00 - Meet Yousuf Khan of Clario

04:17 - Why CIOs Need Group Therapy

05:17 - What AI Changed About the CIO's Job

10:03 - Build or Buy

12:56 - Buying Zoom Before Anyone Else

18:24 - The First Five Minutes

22:06 - A Rollback, and the Apology That Followed

24:46 - From Operator to Investor

34:42 - Leaving Venture to Build Clario

39:53 - Is Silicon Valley Detached?

Eyal Feldman, co-founder and CEO of Stampli, joins Gil Ben-Artzy to talk about the decisions behind building a company: when a founder should hand over sales, why giving everyone AI tools is only part of the work, and the difficult conversations worth having before going into business with your brother.

To most people, an invoice is paperwork. To Eyal, it’s a story waiting to be understood. He left a comfortable corporate career to build a company around a problem he knew well: enterprise software that took months to implement and still left people frustrated.

He started with the questions behind every invoice. Did we order this? Did it arrive? Who needs to approve it? Bringing those conversations together became the starting point for Stampli, the company he built with his brother Ofer. Today, it uses AI to help finance teams manage purchasing, invoices and payments.

New episodes every other Wednesday.
Produced by POLDHU.

CHAPTERS
00:00 - Meet Eyal Feldman of Stampli
03:00 - Leaving Corporate Life to Build Stampli
09:21 - Starting a Company with Your Brother
12:20 - Building the First Sales Playbook
18:09 - Making AI Work Across the Company
24:31 - Looking Past the AI Demo
27:49 - The Future of Finance Work

Michael Bargury on building Zenity and securing the agentic AI frontier.

Zenity just raised $125 million to secure the era of agentic AI in the enterprise.

The rapid adoption of AI agents brings a new set of security challenges for organizations eager to innovate but concerned about how these new systems and AI tools might act inside the enterprise.

Three years ago, Zenity co-founders Ben Kliger (CEO) and Michael Bargury (CTO) were already working with some of the largest Fortune 50 companies on securing low-code and citizen development when generative AI changed the trajectory of the industry—and the company.

They made a bold decision: to follow what they were seeing with customers and refocus Zenity's mission on securing agentic AI.

That decision required immense conviction in their instincts. It also came down to a moment of clarity. During a visit to Microsoft, while Microsoft was shipping its first AI agent product, Michael flew to New York and spent the day walking around Central Park with Ben—five times. By the end of the day, they had decided to leave the old product behind and build for the future they were seeing.

UpWest co-led Zenity's seed round. Today, the company has more than 230 employees and protects Fortune 500 banks, hospitals, and pharmaceutical companies.

In this episode of Runtime, Shuly Galili sits down with Michael to unpack how Zenity went from that pivotal reset to securing what AI agents actually do inside the enterprise.

They discuss where conviction comes from, why "security of AI" is the wrong frame—and "security from AI" is the right one, how sharing a document can plant a false memory in someone's ChatGPT, why agent identity is table stakes and intent is the real problem, how enterprises can roll out new AI tools across an entire fleet in seven days, and why the security stack needs to move from build time to… runtime.

New episodes every other Wednesday.

Produced by POLDHU.

CHAPTERS

00:00   Intro: securing AI agents in the enterprise
03:26   SQL injection at 15, and the years at Microsoft
06:26   Starting Zenity on the unpaved road
07:39   2023: burning what they built
11:10   Security from AI, not security of AI
15:31   The Black Hat demo that hijacks ChatGPT
17:02   What CISOs are measuring wrong
20:58   How fast enterprises are actually moving
27:12   The hacker community, culture, and the team
36:34   Runtime, not build time
40:58   Advice to founders

What happens when the obviously right idea is also the one nobody believes?

Gil Ben-Artzy sits down with Lavi Kwiatkowsky, founder and CEO of Canopy, the company building enterprise AI for oncology. Canopy helps cancer centers care for patients between visits, from monitoring symptoms and flagging emergencies to fielding millions of patient calls and messages, and today works with about 10 percent of oncology patients and providers in the US.

Lavi did not come from healthcare. A bad accident at 23, a missed infection, and years in and out of hospitals showed him how much of care still runs on paper and archaic software. In 2018, he founded Canopy.

They talk about why investors and oncologists alike refused to believe very sick patients would engage with an app, what a satirical BMJ study about parachutes reveals about evidence and medicine, how a flagged headache gave a young patient her remission back, why a finite market means hiring deep experience instead of big sales teams, and how cutting a few years off the decade it takes new therapies to reach patients could mean thousands, maybe tens of thousands of lives.

New episodes every other Wednesday.

Produced by POLDHU.

00:00 Intro: Canopy and enterprise AI for oncology
02:38 The accident that started everything
07:07 Meeting the US market
10:26 The truth no one believed about cancer care
12:58 The parachute problem
16:15 The first customer and the patient who got more time
22:01 Adopting AI without going zero to hero
24:49 Hiring deep, staying lean
31:47 Cutting years off adoption
37:00 Advice to founders and the road ahead

What does it take to build AI for governments—and why is trust the real product?

Shuly Galili sits down with Noam Maital, co-founder and CEO of Darwin AI, the company building the AI guardrails that help governments adopt artificial intelligence safely and at scale.

Noam is a second-time founder. His first company, Waycare, brought AI to traffic management and achieved a successful exit after five years in one of the toughest enterprise markets. Instead of taking a break, he went back to building.

They discuss why government isn't just another vertical but a horizontal market, why trust—not dollars—is the public sector's real currency, how the wave of AI regulation created the opportunity behind Darwin AI, what Noam is doing differently the second time around, and why Israeli founders should build a U.S. go-to-market infrastructure much earlier than they think.

New episodes every other Wednesday.

Produced by POLDHU.

CHAPTERS

00:00   Intro: Darwin AI and guardrails for government

04:37   Selling to government: a different conversation

09:26   Timing the market: the regulation wedge

14:00   Eating your own dog food: going AI-native

18:00   Hiring for the AI era

20:45   What governments actually want from AI

25:38   Where the money is

29:09   Second time around: what changes

36:42   Fundraising: beggar or chooser

44:01   Israel R&D, US go-to-market