Squarespace has crossed $700,000,000 ARR selling just to SMBs, still growing 30% (!)

Enterprise is < 1% of their business

But without the commerce boom, growth would have been much slower

5 Interesting Learnings: ⬇️⬇️⬇️⬇️⬇️
#1. Over $500,000 revenue per employee

Squarespace has 1,200 employees and $700m in ARR. That’s pretty darn efficient

As a result, it’s quite profitable, with $150m in free cash flow in 2020

When your CAC is low, it can be done
#2. Monetizing ecommerce via subscriptions, but not payment processing

Squarespace rapidly expanded into ecommerce, with $3.9 Billion in GMV, up a stunning 91% from 2019. But in contrast to Wix & Shopify, it doesn’t keep much of the revenue from merchant services itself
Rather, it charges for software subscriptions to take payments on its websites.

This ecommerce revenue was $143m in 2020, about 22% of total revenue. But it doesn’t monetize the payments themselves directly very much, unlike Wix

As a result, its margins are higher Image
#3. 85% NRR. Common for self-service & SMBs, but pretty low for public SaaS company

Most higher-churn SaaS & self-serv companies seem to obscure, or at least, not highlight any NRR below 100%.

Wix doesn’t disclose its churn, but it’s likely similar. Image
#4. 70% annual, 30% monthly subscriptions.

Helpful to see, and not inconsistent with other similar self-serve webservices that offer discounts to go annual.
#5. Seasonality: Q1 and Q3 are their strongest quarters.

Squarespace still sees seasonality even at $700m ARR, with Q1 benefitting from new marketing spend at the start of the year, and Q3 benefitting from a holiday rush.

So seasonality is real here at scale.
And a few bonus learnings:

#6. Growth would be mediocre without ecommerce.

Websites revenue (so-called “presence” revenue) only grew 18% -- while ecommerce revenue grew 78%.

Blended together, that worked out to 28% growth
Both Squarespace and Wix would be >much< less interesting companies without their strong ecommerce components.

You have to add a second product to really scale beyond $1B in ARR
#7. Less than 1% of revenue from enterprise customers.

A potential growth path after $1B ARR for Squarespace, but they'll have waited until after $1B+ ARR to truly go upmarket!

Contrast that with Shopify in ecommerce where Plus is a big part of growth story
#8. Founder-CEO Anthony Casalena started Squarespace in his dorm room, controls 68% of the voting rights, and still owns 36% of the company!!

Woah. Casalena maintained such a large share by mostly bootstrapping until growth stage.

Not easy, but it can be done.
A deeper dive here:

saastr.com/5-interesting-…

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More from @jasonlk

3 Apr
So a little more on UiPath

It took UiPath 10 years to go from $0 to $1m in revenue. Yes, 10 years!

Then, it went from $1m to $600m the following 5 years

5+ Interesting Learnings: ⬇️⬇️⬇️⬇️⬇️
First, note UiPath isn't >really< SaaS. Only a small fraction of its customers run in the Cloud

In fact, it might be first IPO in some time where a significant % of customers run the software on Windows!

But, it's priced & sold like SaaS

The definition of "SaaS" has broadened
#1. NPS of 71 and 145% NRR

Yes, NPS can be a bit subjective. And yes, it seems like everyone has a high NPS these days

But having 145% NRR and 71 NPS go together like milk and cookies. They build on each other, into something powerful.

We'll see just how powerful shortly
Read 12 tweets
21 Mar
So Smartsheet is the quiet giant in the productivity space

Asana, Trello, Monday, Airtable, etc. perhaps get more attention

But Smartsheet is at $400m ARR (!) growing a stunning 42% year-over-year!!

5 Interesting Learnings: ⬇️⬇️⬇️⬇️⬇️
#1. Very High NRR from SMBs. Smartsheet has a very impressive 123% NRR from SMBs.

They also nicely segment NRR by deal size, so you can see NRR grows to 140% from their largest enterprise customers:
#2. Driving deal size up accounts for a >lot< of their growth at scale.

Smartsheet has aggressively driven its ACV up from $3,643 in 2020 to $5,103 today. That’s a lot — 40% higher average deal sizes. This just about equals their ARR growth.
Read 7 tweets
19 Mar
I hear lots of new VC Emerging Managers saying they are "going to do an 8x fund" with proud confidence

That's great and something to shoot for

But boy it's hard for a fund of any size
Let's look quickly at the math

If you can put together a $2m-$4m fund, doing 8x is still hard, but doable

Say you own 2% on average, and have 1 Unicorn. That gets you to $20m

That ~8x a $7m fund
Ok great. Now let's say you use your track record to raise a $50m fund.

Now, after dilution, you end up with 5% of each core investment. You try for more, but most seed investments end up w/50% dilution by exit

Now that 1 unicorn nets you $50m. Hooray!

But that's just 1x
Read 6 tweets
18 Mar
Should you pay the same comp to folks, no matter where they work now? A complex topic.

But one thing is clear: the vast majority of sales leaders I've talked to are continuing to localize comp

Why? They always have. It's not new.

What is new is where the top AEs work
The common pattern pre-Covid was to build up your core, expensive AE team first in SF Bay Area

And then move at least SMB sales, SDRs, etc. to a lower cost center like Phoenix, Portland, Atlanta, Florida, etc.

But now, top AEs are scattered across U.S.
The short-term effect is that an AE in the Bay Area often makes more than an AE hitting the exact same quota in say Denver (to adjust for COL and competition)

But what will 2021/2022 bring?

There will be more pressure not to pay Bay Area AEs 20%+ more vs. closers anywhere else
Read 5 tweets
6 Mar
VC Humblebrags

They’re insufferable, omnipresent and hubristic

But >why< do VCs do so much humblebragging?

It’s not just arrogance:
1/ First, understand this is how VCs are taught and raised. The average Monday VC partner meeting is a bunch of subtle and not-too-subtle flexing around who has the hot companies. That’s where the power is. So you sort of learn to do this from Mom and Dad.
2/ As a VC, you yourself are just a number.

Your LPs know the numbers — and view you as a number. Many firms say “we don’t do attribution”, but everyone knows who sourced & closed the top deal(s)

And LPs figure it out and do their attribution analyses

You are just a number
Read 7 tweets
5 Mar
The #1 thing that will stop you after $4m-$5m is burn-out

It’s not competition
It’s not market change
It’s not VC funding

Almost any founder who’s crossed it will tell you that
It’s not enough to “take care of yourself”, although of course that matters.

Take your vacations. Unwind as much as you can on the weekends, etc. Join peer groups.

But the only answer to burn-out is hiring a great management team

This is job #1, #2, and #3 after $1m ARR
A truly great management team solves for all other problems once you have Initial Traction, just a few million in ARR:

- they out innovate the competition
- they outsell the competition
- they close the feature gaps that matter
- they get your NPS up, and churn down
Read 6 tweets

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