20VC: How Wiz Built a $30BN Brand in Enterprise: Lessons Learned, Mega Failures, and Why Marketers Make the Worst CMOs (with Raaz Herzberg, 12 Dec 2025)

Episode Overview

In this deeply candid and practical episode, Harry Stebbings sits down with Raaz Herzberg—Chief Marketing Officer and VP of Product Strategy at Wiz, the fastest-growing cloud security company ever valued at $30B. Raaz, who joined as one of Wiz’s first 10 employees, shares how she navigated building an iconic enterprise brand, why non-traditional marketers and creativity trump classic approaches, the critical role of product-market fit, and why most marketers make terrible CMOs. Packed with vivid examples, humility, and actionable insights, this episode is a masterclass for B2B founders, marketers, and product leaders destined for enterprise greatness.

Key Discussion Points and Insights

Imposter Syndrome & Relentless Drive

(03:47)

• Raaz normalizes and embraces impostor syndrome:

  “I always feel like an imposter. …It’s part of the motivation. …I’m always paranoid about everything. …Never complacent about anything.” — Raaz Herzberg (04:00)

• This constant self-doubt, she says, fuels her edge and relentless preparation, even after “thousands” of customer meetings.

Product-Market Fit & the Birth of Wiz

(05:27)

• Raaz attributes Wiz’s unprecedented enterprise growth to a trifecta:
  • Clear, urgent problem: “For security teams, there’s a before Wiz and after Wiz moment.”
  • Incredible time-to-value: “With Wiz…you get value in 15 minutes.”
  • COVID acceleration: “Everyone was moving faster to the cloud; it made the problem huge.”
• Early team did everything—from sales to legal—to keep up with demand.

On Not Losing a Deal

(07:21)

• When asked about her track record:

  “I’m just very, very afraid of failing…Every deal, I feel like my life depends on it.” — Raaz (07:37)

• She once spent two years closing a customer after an early rejection, driven by the need to “prove herself wrong.”

The Non-Traditional Marketer & Why ‘Marketers Make the Worst CMOs’

(09:53, 57:14)

• Raaz insists deep product and customer understanding matter more than classic marketing training:

  "I'm not a marketing expert…I don't think I could do marketing at any other company." "I hire people who don’t want to be marketers." — Raaz (09:53)

• Non-traditional creativity is essential:

  “Marketing…is about people who can be creative, think of a solution, and be amazing at execution. If it doesn’t work, don’t do it again.” (11:30)

• Traditional CMOs, she says, are often “too careful,” lacking the creative license required to truly stand out; external CMOs rarely have the trust or risk appetite to do what’s needed.

High-Impact Brand Moves: The ‘Wiz of Oz’ Booth

(12:32)

• Her first marketing act: Turn Wiz’s RSA booth into a full “Wizard of Oz” experience—with balloon props and actors.
• Outcome: 4x more leads vs. traditional designs.

  “It brought in 4x more leads…because everybody came to see what is that company?” — Raaz (13:00)

• Lesson: “Doing something yellow and weird doesn’t cost more than doing it black and boring.” (13:10)

Learning from Failures: Pivoting Early & Misunderstanding Product Marketing

(14:58, 16:11)

• Biggest mistake: Not understanding or valuing product marketing—originally thought it was just “the team that writes the blogs.”
• Humbling, critical lesson about building go-to-market muscle.
• Early product was misdirected (in network security):

  “We were convincing ourselves…there was interest, but we couldn’t get to the next step…huge learning.” (16:11)

The Underrated Power of Brand (vs. Pipeline Metrics)

(17:29-19:04)

• Brand is the most underappreciated growth vector in enterprise:

  “Sometimes things that are very hard to quantify, like brand, are actually the things that matter most." — Raaz (17:44)

  • “You can build a team obsessed with pipeline numbers, but at the end, brand warmth matters more.”
• Metric that matters: “How warm is the room when you walk in?”

Building Authenticity: Humor, Humanity, and Warmth in Enterprise

(21:02, 22:29)

• Fear-based security marketing (“scaring people”) is passé at Wiz:

  “I don’t think people are looking for more scariness, formalness…Humor connects people more than fear.” (21:02)

  • Reminds us that buyers are people first—even in Fortune 500s.

Enterprise Go-to-Market: Starting Upmarket & Leveraging Prior Knowledge

(24:58, 25:09, 27:12)

• Wiz started upmarket; first customer was a Fortune 10 company.
  • Key enabler: Founders' Microsoft/Azure Security experience, which embedded a “scale mindset” from day one.

  “If you can help the most complex…regulated organizations adopt you, your way downmarket becomes easier.” — Raaz (25:09)

• But it wasn’t their “name,” but their deep understanding of enterprise that opened the doors.

Lessons from Microsoft: Build for Infinite Scale

(28:21-31:56)

• Microsoft drilled two golden rules:
  1. Build for infinite scale—if it breaks at scale, don’t build it.
  2. Sales to the world’s largest organizations requires an impeccable machine.
• Building with refactoring in mind kills velocity; bake scale in from the start.

Handling Custom Feature Requests & Maintaining the North Star

(31:24-34:58)

• Stay true to your domain:

  “If it doesn’t align to the North Star—securing cloud apps for security/dev teams—it’s out of scope.” (34:39)

• Major product metrics: Customers achieving "Zero Criticals" (no unresolved critical risk) & share of non-security (developer) users in the platform.

What Not to Do in Enterprise Sales

(37:30-39:02)

• Breaking into massive accounts has little to do with classic marketing channels:
  • “It’s about finding your first ‘one’ champion, doing an amazing job, and letting referrals snowball.”
• Optimize for true value, not short-term revenue (“I made the worst deals ever—didn’t matter”).

POVs/Pilots: Time to Value is Value

(39:02)

• Wiz focused on reducing time-to-value in pilots (“less than an hour”)—a huge enterprise GTM advantage.

Prioritizing Customer Interests & the Power of Sizable Funding

(40:36-44:36)

• “What’s best for the customer is always best for the company”—even if short-term tradeoffs arise.
• Acknowledges that selling to enterprise often requires larger seed rounds:

  “It’s hard to be successful at building an enterprise company without having…long pockets." (44:00)

Winning, Culture, and Adaptability

(49:50-52:59)

• Execution speed (“winning") shapes culture at Wiz.
• But people/culture do matter: “You need people from a specific type. …That’s what culture is about." (50:10)
• Success at startups requires adaptable people who reinvent themselves every 3–4 months.

The Impact of Starting Remotely & Not being a Silicon Valley Company

(53:23-54:59)

• COVID allowed Wiz to outcompete US-headquartered businesses without being in Silicon Valley.

  “All we did was work for a year…nobody knew we were sitting at our home in Tel Aviv.” (53:34)

Lessons in Leadership & Hiring

(57:14, 59:08)

• “Most CMOs aren’t good”—too careful, too wrapped in traditional thinking.
• You don't need to be “a marketer” to be a great CMO—must be grounded in the product, customer, and creativity.
• Marketing is not that complicated:

  “People overly complexify it…You can look at what Wiz does and know if it’s good or bad because you’re a human being.” (58:00)

The Role of AI Today & Tomorrow

(62:02–64:32)

• Every day, AI’s capabilities are transforming Wiz’s teams—brand/design, product, etc.—at breakneck speed.
• “Definition of ‘engineer’ will broaden. If an engineer is someone who builds things, that’s becoming a bigger category.”
• On code: Fundamentals/principles matter more than language, even as LLMs change how coding is done.
• Internally, built “Marilyn,” a custom internal AI agent that turbocharges go-to-market execution and enables scaling across languages/regions.

The Real Future of SaaS

(70:23–73:18)

• Building your own tools (like Marilyn) is possible if you have engineering access; otherwise, most sales/marketing teams remain dependent on third-party SaaS due to complexity and lack of developer resources.

Notable Quotes & Memorable Moments (w/ Timestamps)

• “I always feel like an imposter. …It’s never left me throughout my career, and I embrace it.” — Raaz (03:47)
• “Wiz had an incredible product-market fit early on. …We believed that time to value is value.” — Raaz (05:27)
• “I’ve never lost a deal at Wiz, but I’m always afraid of that happening.” — Raaz (04:33)
• “Marketing is not that complicated. …I think people overly complexify it.” — Raaz (58:00)
• “Doing something yellow and weird doesn’t cost more than doing it black and boring.” — Raaz (13:10)
• “Brand is underrated…Brand matters more than pipeline numbers. The warmth of the room is what matters.” — Raaz (17:44)
• “Find the one [enterprise] champion you can win over, deliver value, and let referrals snowball.” — Raaz (37:30)
• “If it doesn’t align to the North Star, it’s out of my scope.” — Raaz (34:39)
• “Winning generates a team of people of a specific type. That’s what culture is about.” — Raaz (50:10)
• “Most CMOs aren’t very good…It’s a hard job. Also, marketing is not that complicated.” — Raaz (57:14; 58:00)
• “The ability to wake up every morning and change your mind is mandatory in the current AI era.” — Raaz (62:02)
• “I think the best leaders—and investors—are always deeply thoughtful, never on autopilot.” — Raaz on Shardul Shah (60:08)

Timestamps for Key Segments

| Time | Segment Title | |---------------|------------------------------------------------------| | 03:47 | Embracing Impostor Syndrome & How It Drives Raaz | | 05:27 | What Created Wiz’s Early, Explosive Product-Market Fit| | 07:21 | Never Losing a Deal: Obsession & Paranoia | | 09:53 | Why Product Knowledge Beats Traditional Marketing | | 12:32 | The ‘Wiz of Oz’ RSA Booth (Creative Brand Bets) | | 14:58 | Early Failure: Misunderstanding Product Marketing | | 17:29 | Brand > Pipeline Metrics: Making the Room Warm | | 21:02 | Humor, Not Fear—How Wiz Connects w/ Serious Buyers | | 24:58 | Starting Upmarket: Why (and How) It Worked | | 28:21 | Lessons from Microsoft on Infinite Scale | | 31:24 | Handling Custom Feature Requests | | 34:39 | Defining and Measuring the North Star | | 37:30 | Enterprise Sales Mistakes: Forget Classic Marketing | | 39:02 | POVs and Cutting Time-to-Value in Enterprise | | 40:36 | Is “What’s Best for Customer” Always Best for You? | | 44:00 | Raising Big Seeds for Enterprise Startups | | 49:50 | Culture, Winning, and Type of Teammates | | 57:14/58:00 | Why Most Marketers Make Bad CMOs | | 62:02 | AI Changes Everything—Daily | | 68:02 | Internal AI Tools (‘Marilyn’) | | 70:23 | Will Custom Tools Replace SaaS? |

Actionable Lessons for Founders & Marketers

• Build for unambiguous value and instant time-to-value—even in complex enterprise products.
• Brand matters for enterprise: warmth in the buyer’s room trumps “green” pipeline dashboards.
• The best marketers deeply understand the product, customers, and domain pain points.
• Creativity and humor are underutilized differentiation levers, even in conservative industries.
• Large enterprise GTM boils down to attaining a small set of influential referrals—don’t concentrate on mass marketing.
• Hire for adaptability and a ‘doer’ mindset; company context evolves every 3–6 months.
• Don’t be afraid to break tradition: non-traditional marketers can often outperform the classic hires if they have trust, context, and creative carte blanche.

This summary captures the key insights, stories, and philosophy from Raaz Herzberg’s journey scaling Wiz. Essential listening (or reading!) for B2B founders, marketers, and product executives aiming to disrupt long-standing enterprise markets with boldness, clarity, and authenticity.