The Risk (and Reward) of Standing Out: Why Your Story Shouldn't Fit a Mold
2/2/25 Benchmarks for Operators
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When Monday.com was preparing to go public, the typical IPO playbook was laid out in front of them. The banks, the analysts, the advisors—everyone had an opinion on how to tell their story in a way that would resonate with investors. But instead of conforming, Monday’s leadership did something counterintuitive: they insisted on telling their OWN story, even if it meant standing out.
Eliran Glazer, CFO of Monday.com, shared with me how their team resisted the pressure to conform to the “cookie-cutter” approach of an IPO roadshow. Instead, they doubled down on the unique DNA of their company—one built on flexibility, authenticity, and the idea that they weren’t just selling software, but something bigger.
And guess what? Investors took notice.
And four years later, Monday.com trades at a premium revenue multiple.
The Pressure to Fit a Narrative
If you’ve ever been through an IPO, a fundraising round, or even a high-stakes investor presentation, you know the drill. There’s a formula:
Define your TAM (Total Addressable Market).
Position yourself within a well-established category.
Draw clear comparisons to competitors.
Tell a story that makes you easy to analyze.
This makes sense on paper. If you’re easy to categorize, you’re easier to invest in. Analysts want to slot you into an existing mental model because it helps them make quick decisions. It’s an understandable, yet selfish, ask in many ways. But the danger is if you blend in too much, you become just another company in a sea of similar-looking options.
That’s exactly what Monday.com wanted to avoid.
“You have to make sure that you differentiate yourself because you come to this audience of analysts and investors, and they can say in their heart, ‘Okay, what's in it for me? Why should I listen to this? I'm already looking at 15 IPOs, how is Monday unique?’”
-Eliran Glazer, CFO of Monday.com
Conviction in Your Own Story
Monday’s co-founders, Roy Mann and Eran Zinman, didn’t just want to optimize for the perfect IPO price. They wanted to be true to what made the company different. “They had strong conviction in their story,” Eliran explained. “This is how we want to tell our story. This is what we believe in.”
The company had a message that was different from other productivity and collaboration tools like Asana and Smartsheet. Instead of positioning Monday as just another software company, they leaned into something unexpected: Monday.com wasn’t selling software, it was selling building blocks.
Instead of telling customers, “Here’s our project management tool,” they told them, “Take these blocks and build the software of your dreams.”
That framing changed everything. It positioned Monday not as a point solution, but as a platform with infinite flexibility. The company made the bold claim that they could serve any industry in any geography for any size of business—from a two-person startup to a 25,000-person enterprise.
That approach didn’t fit into a predefined box. And that was the point.
When you do that, it also shows authenticity, which helps you build lines, rather than dots, with investors.
The Power of Authentic Story Telling
Eliran shared a story about an investor who reflected on his time holding Monday. One of the things that stuck with him about Monday’s leadership? Their authenticity.
“When we spoke with you,” the investor told Eliran, “we felt like you were seeing the person behind the conversation. You weren’t just selling something—you actually believed in it.”
That’s a rare compliment in a world where CFOs are often seen as number-crunchers first, storytellers second. But the best finance leaders know that numbers alone don’t move markets—stories do. Stories that have an authentic human element to complement the numbers.
Being Bold in Your Storytelling
As the roadshow progressed, they leaned harder into these differentiators.
This required boldness.
Eliran’s advice to other companies: stick with your story, even if it’s not the “safe” one.
“Even if people tell you your story is not the playbook investors are used to, if you believe in it—if you have conviction—stick with your truth,” he said. “The founders know best why they built the company. They know the pain point they’re solving. Make sure you know how to tell that story.”
That’s a refreshing take in a world where founders often feel pressured to shape their story to fit what they think investors want to hear.
Differentiation Wins
At the end of the day, differentiation isn’t just a marketing tactic—it’s an economic moat.
Monday.com succeeded because they didn’t let investors or bankers dilute their message. They leaned into their unique vision, even when it would have been easier to conform.
And investors liked that.
Your company’s story isn’t just a pitch—it’s the reason customers buy, employees join, and investors bet on you. If you try too hard to fit in, you’ll be forgotten. But if you’re bold enough to stand out, you’ll be impossible to ignore.
Apple | Spotify | YouTube
TL;DR: Multiples are DOWN week-over-week.
Top 10 Medians:
EV / NTM Revenue = 16.9x (DOWN 0.7x w/w)
CAC Payback = 27 months
Rule of 40 = 53%
Revenue per Employee = $386K
Data Source: Koyfin
Figures for each index are measured at the Median
Median and Top 10 Median are measured across the entire data set, where n = 110
Population Sizes:
Security: 17
Database and Infra: 14
Backoffice: 16
Marcom: 16
Marketplace: 15
Fintech: 16
Vertical SaaS: 16
Revenue Multiples
Revenue multiples are a shortcut to compare valuations across the technology landscape, where companies may not yet be profitable. The most standard timeframe for revenue multiple comparison is on a “Next Twelve Months” (NTM Revenue) basis.
NTM is a generous cut, as it gives a company “credit” for a full “rolling” future year. It also puts all companies on equal footing, regardless of their fiscal year end and quarterly seasonality.
However, not all technology sectors or monetization strategies receive the same “credit” on their forward revenue, which operators should be aware of when they create comp sets for their own companies. That is why I break them out as separate “indexes”.
Reasons may include:
Recurring mix of revenue
Stickiness of revenue
Average contract size
Cost of revenue delivery
Criticality of solution
Total Addressable Market potential
From a macro perspective, multiples trend higher in low interest environments, and vice versa.
Multiples shown are calculated by taking the Enterprise Value / NTM revenue.
Enterprise Value is calculated as: Market Capitalization + Total Debt - Cash
Market Cap fluctuates with share price day to day, while Total Debt and Cash are taken from the most recent quarterly financial statements available. That’s why we share this report each week - to keep up with changes in the stock market, and to update for quarterly earnings reports when they drop.
Historically, a 10x NTM Revenue multiple has been viewed as a “premium” valuation reserved for the best of the best companies.
Efficiency Benchmarks
Companies that can do more with less tend to earn higher valuations.
Three of the most common and consistently publicly available metrics to measure efficiency include:
CAC Payback Period: How many months does it take to recoup the cost of acquiring a customer?
CAC Payback Period is measured as Sales and Marketing costs divided by Revenue Additions, and adjusted by Gross Margin.
Here’s how I do it:
Sales and Marketing costs are measured on a TTM basis, but lagged by one quarter (so you skip a quarter, then sum the trailing four quarters of costs). This timeframe smooths for seasonality and recognizes the lead time required to generate pipeline.
Revenue is measured as the year-on-year change in the most recent quarter’s sales (so for Q2 of 2024 you’d subtract out Q2 of 2023’s revenue to get the increase), and then multiplied by four to arrive at an annualized revenue increase (e.g., ARR Additions).
Gross margin is taken as a % from the most recent quarter (e.g., 82%) to represent the current cost to serve a customer
Revenue per Employee: On a per head basis, how much in sales does the company generate each year? The rule of thumb is public companies should be doing north of $450k per employee at scale. This is simple division. And I believe it cuts through all the noise - there’s nowhere to hide.
Revenue per Employee is calculated as: (TTM Revenue / Total Current Employees)
Rule of 40: How does a company balance topline growth with bottom line efficiency? It’s the sum of the company’s revenue growth rate and EBITDA Margin. Netting the two should get you above 40 to pass the test.
Rule of 40 is calculated as: TTM Revenue Growth % + TTM Adjusted EBITDA Margin %
A few other notes on efficiency metrics:
Net Dollar Retention is another great measure of efficiency, but many companies have stopped quoting it as an exact number, choosing instead to disclose if it’s above or below a threshold once a year. It’s also uncommon for some types of companies, like marketplaces, to report it at all.
Most public companies don’t report net new ARR, and not all revenue is “recurring”, so I’m doing my best to approximate using changes in reported GAAP revenue. I admit this is a “stricter” view, as it is measuring change in net revenue.
Operating Expenditures
Decreasing your OPEX relative to revenue demonstrates Operating Leverage, and leaves more dollars to drop to the bottom line, as companies strive to achieve +25% profitability at scale.
The most common buckets companies put their operating costs into are:
Cost of Goods Sold: Customer Support employees, infrastructure to host your business in the cloud, API tolls, and banking fees if you are a FinTech.
Sales & Marketing: Sales and Marketing employees, advertising spend, demand gen spend, events, conferences, tools.
Research & Development: Product and Engineering employees, development expenses, tools.
General & Administrative: Finance, HR, and IT employees… and everything else. Or as I like to call myself “Strategic Backoffice Overhead.”
All of these are taken on a Gaap basis and therefore INCLUDE stock based comp, a non cash expense.
Really enjoyed the content around Monday.com here - my org is a fan and we're a customer.
I think we'll see more of these calculated bets as many software platforms hit that "commodity" stage. Otherwise it's a race to the bottom of the margin barrels.
Balancing not fitting a mold while not inducing too much risk is such a fine balance.