There's a moment in time in every SaaS company where money doesn't really matter anymore. You have enough to hit your goals.

And there's a much earlier moment in time where every single dollar matters.

Between the two is the art of investing your balance sheet as a SaaS CEO
Invest too little in this phase, and you waste time. Sometimes a lot of it.

You don't hire real VPs. You don't build that integration.

You'll look back and deeply regret wasting this time.
Invest too much in this phase, and you probably don't go bankrupt, but you overspend and have to painfully hit the brakes

This is equally brutal and can set you back a year or more
A few simple thoughts:

1/ Find a way to make every accretive hire after $2m ARR. Just find a way.

After $2m ARR, every great engineer, every great AE, every great CSM will pay for themselves

Just not in a day
2/ Remember the Balance Sheet Rule

You want to have at least 50% of your ARR on your balance sheet. If you don't, you will underinvest. Always.

So at $4m ARR, you need at least $2m inbank to invest

At $10m ARR, you need at least $5m in bank to invest

As CEO, get it done
3/ Don't underhire in this phase ($2m-$10m ARR, usually)

This also subtly sets you back months and often even a year

After $2m ARR, it's OK to make a stretch hire

But a stretch hire that is a real VP. Not a manager.

This doesn't save money. It costs money.
A related post here:

saastr.com/from-initial-t…

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More from @jasonlk

24 Jul
So Avalara is a Quiet Giant in SaaS -- that you don't know enough about

At $600m ARR, growing 38%+, it does something both boring AND hard

It sells tax compliance software to SMEs

5 Interesting Learnings: ⬇️⬇️⬇️⬇️⬇️
#1. 15,580 customers, up 20% year-over-year — or $40,000 per customer per year on average.

NRR is 107%, fairly consistently over the past 4 quarters. Good but not great for a $40k deal.

What they do is mission critical, so ACVs from SMEs are pretty high
#2. 1000 partners are key to their GTM strategy. And “in 950 of the partners, Avalara has no competition”.

Like HubSpot, Shopify and other leaders that sell sophisticated, $10k+ solutions to SMEs, partners are key to implementation.

They invest >heavily< here
Read 11 tweets
19 Apr
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
Read 12 tweets
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

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