For weeks Raaz sat on every customer call and still didn't understand what Wiz was building, assuming she was the only confused one. When she finally admitted it, it turned out no one fully understood, and that admission opened the five-hour discussion that led to the pivot. She credits Wiz's flat, ego-free culture for making it safe to say 'I don't understand.'

It takes real courage to admit you don't understand, especially as the expert in the room
Everyone assumed clarity existed; nobody actually had it
Saying 'I don't understand' became her favorite question over her career
A flat culture where voices are heard regardless of title makes this possible

“it's hard to get the courage to say actually I don't understand but I think by now in my care it's like my favorite question”
Raaz Herzberg · 15:30

#leadership#culture#communication

Hot Take21:00

If the Founding Team Can't Do It, Don't Expect a Hire To

Wiz sold several million in ARR before hiring its first salesperson, with the founders closing contracts themselves. Raaz argues that if the core team can't do something end-to-end, hiring an outsider to solve it is usually wishful thinking. Doing it yourself first also gives you the confidence and proof to hand a new hire.

The founders closed a couple million in ARR before their first sales hire
Doing sales themselves taught them the process end-to-end
If the core team can't do it once, an outside hire rarely fixes it
Selling it yourself first gives your first salesperson proof and confidence

“if you can't do it one time and to end then you like the core core Core Group the chances of just bringing somebody from…”
Raaz Herzberg · 22:30

#startups#hiring#b2b-sales#founders

Hot Take34:00

Why CMOs Fail: Marketing Is Visible and Trust Breaks Easily

Raaz argues the CMO role is uniquely hard because everything marketing does is public and touches something founders care about deeply. Trust with the founding team is hard to build and easy to break, one off-brand ad can do it. She also thinks a CMO needs deep, native understanding of the product and market, which is hard to gain from outside.

Everything in marketing is highly visible to founders and the world
One bad ad the founders reject can break hard-won trust instantly
A CMO needs deep connection to both the product and the market
Coming from outside the founding team and outside a technical market is a double challenge

“like one bad ad or something that one of the founding team will say like oh this is not us this is like not what…”
Raaz Herzberg · 34:30

#marketing#leadership#trust#cmo

Hot Take53:30

Embrace Imposter Syndrome Instead of Trying to Build Confidence

Raaz's contrarian take on the standard 'build your confidence' advice given to women in tech: she can't manufacture confidence and does feel like an imposter, so she just embraces it. Rather than letting the feeling stop a decision, she lets people 'find her out' if they will, and applies for the role or takes the shot anyway. You never learn your limit if you don't try.

She rejects the standard advice to fight imposter syndrome by building confidence
Everyone feels like an imposter, so embrace it instead
Don't let the feeling stop you from making a decision or taking the shot
You'll never know your limit if you don't try

“maybe embrace it but don't let that um stop you from from making a decision like maybe they will find out your random poster maybe…”
Raaz Herzberg · 54:30

#mindset#career#confidence#women-in-tech

Explainer· 2

Explainer28:00

The 'Heat' Metaphor: Where the Pressure Moves as a Company Grows

Raaz describes company-building as heat moving through the org over time. It starts in the product kitchen (figure out what to build), shifts to engineering (build it), then to sales (go sell it), then to marketing (nobody's heard of us, give us pipeline). She sees the best people naturally getting placed wherever the heat and the biggest bottleneck currently are.

Early on the heat is in product: figuring out what people want
It moves to engineering to build, then to sales to sell the first deals
Then heat moves to marketing when sales demands more pipeline and awareness
Leadership puts the best people where the company needs the most help

“in the early early days when we just started whiz I remember I felt like the heat was in the product kitchen”
Raaz Herzberg · 28:00

#scaling#leadership#org-design#marketing

Explainer45:00

The Bubble and the 'Dummy Explanation': Stop Assuming Customers Know Your Jargon

Raaz warns that living inside your own company creates a bubble where you assume the market knows your terminology. Wiz's team called the category 'CNAP,' but customers were Googling 'cloud security solution.' Her fix is the 'dummy explanation': write everything so any outsider understands it, and remember you're the only one sick of your own website copy, customers are just now learning it.

Insiders use internal terms like CNAP while buyers search 'cloud security solution'
The 'dummy explanation' means assuming no knowledge of your company, product, or market
Drop internal jargon like 'the Wiz graph database' that a common person wouldn't know
You're the only one tired of your messaging; customers are still just grasping it

“if you go over and you like look at Google like people are not Googling that word they're Googling like Cloud security solution”
Raaz Herzberg · 48:00

“you the only one that is sick of it right your customers are just learning what you put there like 10 months ago”
Raaz Herzberg · 50:30

#marketing#messaging#positioning#communication

Story· 3

Story11:30

Why Founding Wiz During the COVID Lockdown Was a Hidden Advantage

Wiz was founded in March 2020 just as the world shut down, and even Raaz's mom told her it was a bad time to join a startup. But because everyone was suddenly home with no meetings or travel, normally-busy CISOs were available for back-to-back calls. The team ran 10-15 discovery calls a day, which is how they rapidly learned what wasn't working.

Wiz was founded the same month the world locked down for COVID
Lockdown meant busy security buyers were home and available for calls
The team ran 10-15 back-to-back customer calls per day
High call volume is how you quickly find what isn't working and what is

“even my mom was like calling me and telling me this is not a good time to join a startup but it ended up being…”
Raaz Herzberg · 12:00

#customer-discovery#startups#founding-story

Story19:00

The Scary Questionnaire That Proved a Customer Actually Wanted It

Facing an early POV with a Fortune 10 company before the product was ready, Raaz sent a long list of technical questions partly to buy time, terrified it would scare the customer off. It came back fully filled out a day later. The lesson: friction filters for real commitment, and you should look for pull from the customer rather than pushing.

A long, annoying prerequisite questionnaire tests whether the buyer is truly committed
The Fortune 10 prospect returned the filled-out list the next day
You want the customer's pull, not to push someone into a POV
Commitment from the buyer matters because early adoption is a shared journey

“I want to make sure they're committed right I don't want to push somebody into a POV if he is not committed to me at…”
Raaz Herzberg · 20:00

“don't be too afraid to um get the pull from the customer like it's okay like you need that pull from the other end as…”
Raaz Herzberg · 20:30

#b2b-sales#product-market-fit#customer-discovery

Story38:00

The Wizard of Oz Booth That Got 5x the Traffic at RSA

For Wiz's first RSA (the 'Super Bowl of security'), Raaz scrapped the standard dark, scary cyber booth and built a Wizard of Oz booth with actors like Dorothy, going bright, pink, optimistic and magic-themed. Terrified it would flop, she instead drew five times the foot traffic of the prior year in the same space, and themed booths became a Wiz signature others now copy.

RSA is the biggest security industry conference where all buyers gather
She replaced a classic cyber booth with a bright, optimistic Wizard of Oz theme
Same booth space and investment drew 5x the visitors of the previous year
Themed booths became a recurring Wiz tactic that competitors now imitate

“let's scrap our booth and do a whiz of Oz Booth which literally looked like a wiz of osoth”
Raaz Herzberg · 38:30

“the amount of people that stopped by your booth was like um five times the amount of people that stopped by the year before”
Raaz Herzberg · 40:00

#marketing#branding#events#differentiation

Tool· 1

Tool56:30

Raaz Herzberg's Book Recommendations: Setting the Table and No Rules Rules

Raaz recommends 'Setting the Table' by Danny Meyer (Shake Shack) for its customer-obsession and hospitality lessons that transfer well to tech and SaaS. Her second pick, read by the whole Wiz founding team, is 'No Rules Rules' by Netflix co-founder Reed Hastings, which she values for its lessons on building a strong culture capable of dramatic pivots.

'Setting the Table' by Danny Meyer: customer obsession and hospitality applied beyond restaurants
Shake Shack optimizes for you to sit down, unlike most chains
'No Rules Rules' by Reed Hastings, read by the whole Wiz founding team
Netflix's culture enabled radical pivots from mailing DVDs to production studios

“one of my most favorite business books in read like a lot of them is um probably setting the table by by Danny Mayer”
Raaz Herzberg · 56:30

#books#culture#leadership#recommendations

Takeaway· 5

Takeaway10:30

How Wiz Knew Its First Idea Wasn't Working: Politeness Isn't a Signal

Wiz started as a network-security company called Beyond Networks, running 10-15 customer calls a day where prospects kept saying 'sounds interesting, would love to hear more.' Raaz realized those warm-but-vague responses were affirmation, not enthusiasm, and that the team was listening for reinforcement instead of real demand. Recognizing the difference is what pushed them to pivot to cloud security.

Prospects who say 'interesting, tell me more' are often just being polite to a smart-seeming team
Humans are biased toward seeking affirmation rather than hearing what they don't want to hear
The team was looking for positive reinforcement, not signs of deep enthusiasm
Reframing what a good signal looks like triggered the pivot to cloud security

“we were looking for like positive reinforcements but not really listening intently to like signs of deep enthusiasm”
Raaz Herzberg · 11:00

“I think naturally as human beings you want to get affirmation from the other side so you're actually you have a bias to look for…”
Raaz Herzberg · 13:30

#product-market-fit#customer-discovery#startups#pivot

Takeaway13:00

What Real Product-Market Fit Actually Sounds Like on a Call

Once Wiz landed on cloud security, the type of questions on calls changed. Instead of vague enthusiasm, prospects asked about pricing, when they could issue a purchase order, and who to connect the team to internally. Raaz learned to look for that active pull toward the next step as the true signal of demand.

Weak signal: 'sounds interesting, please update me'
Strong signal: 'how are you pricing this?' and 'when can we start a PO?'
A prospect volunteering to connect you to their internal team is a strong buy signal
Look for the customer pushing toward the next step, not just praise

“suddenly the call sounded like wait again how are you pricing this how much will this cost or wait like when can we start doing…”
Raaz Herzberg · 13:00

#product-market-fit#b2b-sales#customer-discovery

Takeaway24:30

Why Brand Matters Even for the Most Technical B2B Buyers

Two and a half years in, Wiz had clear product-market fit but kept losing deals to competitors customers had simply heard of first. Raaz took on marketing convinced that awareness and brand were the next scaling bottleneck. Her point: even technical B2B buyers are still people who buy on brand, the same way most people buy an iPhone without reading the specs.

Wiz would win any head-to-head POV but lost deals where buyers never heard of them
Awareness became the scaling bottleneck after product-market fit and sales
People buy an iPhone on brand, not by comparing specs to Android
Even the most complex B2B products are bought by people, so brand matters

“when I buy my iPhone I have no idea how it really is compared to an Android phone I did not look at the specs…”
Raaz Herzberg · 27:30

“B2B products even the most complex products people are still people they still buy it because brand matters a lot”
Raaz Herzberg · 27:30

#marketing#branding#b2b#scaling

Takeaway36:30

Marketing Is the Opposite of Product: There's No Cost to Trying

As a PM, Raaz believed less is more because every feature carries permanent engineering cost and complexity you can rarely take back. Marketing, she realized, is the opposite: a video that flops costs nothing and is forgotten by tomorrow. That freed her to try everything and make noise, treating low downside as an advantage.

In product, every added feature has huge permanent cost and can't be taken back
In marketing, a failed post has no maintenance and no lasting cost
Low downside means you can experiment aggressively
Her strategy was simply to try everything and make noise

“if tomorrow I post a video on Wizz LinkedIn page and I think that video is super funny and nobody likes that video nothing happened…”
Raaz Herzberg · 37:30

#marketing#product-management#experimentation

Takeaway40:30

Being Okay With Failing: Why Friction Is Good

Raaz says she's taken almost every role, including joining Wiz and moving to marketing, convinced she'd probably fail, and did it anyway. She traces the mindset to her mother, who pushed her into the areas she was weakest rather than doubling down on her strengths, believing friction and hard work beat talent. Giving yourself permission to fail is what she finds empowering.

She's attempted most of her career moves expecting to fail
Her mother pushed her toward weaknesses, not strengths
The 'friction is good' idea: like brushing where your gums bleed, push harder there
Hard work and courage beat talent, which only gets you so far

“I'm kind of okay with being pretty sure I'm going to fail at something and still attempting it”
Raaz Herzberg · 41:00

“if you brush your teeth and there's like a bit of blood somewhere then you need to brush harder there it's kind of like that…”
Raaz Herzberg · 43:30

#mindset#failure#career#personal-growth

Frameworks in this episode

Do It End-to-End Before You Hire For It

Embrace the Imposter: Act Despite Expecting to Fail

Follow the Heat

Marketing's Reversibility Advantage: Try Everything, Make Noise

Pull, Not Praise: Reading Real Product-Market Fit Signals

The Dummy Explanation (Escape Your Bubble)

The Friction Commitment Test

Insights & moments

◆Hot Take· 4

Why 'I Don't Understand' Became Raaz's Favorite Question