Coupa is a $16B SaaS success story anyone selling mid-market and enterprise should know more about

They dominated their Web 1.0 predecessor (SAP Ariba) and grew the TAM of their space, Spend Management, 20x

5 Interesting Learnings: ⬇️⬇️⬇️⬇️⬇️
#1. Network effects are real in many spaces in SaaS, like Spend Management

Coupa now manages $2.5T in spend management over 7 million suppliers. Could you switch to another vendor? Yes. Would you want to? No. Imagine how many vendor relationships that would be to switch over
#2. 80% of implementations led by partners, with 5,000 trained partner consultants

The really big deals & even smaller ones are deployed by partners. 80% of deals. The “biggies” are Accenture, KPMG, and Deloitte. But Coupa has implementation partners across all segments
3. Even at $700m in ARR, Coupa has only closed 2,000 of 100,000 target customers. 2%.

There’s just so much room to run in SaaS now. Even at $700m ARR, they’ve just scratched surface. Cloud is huge. This is why all the SaaS leaders seem to have almost unlimited room for growth
4. Serves both mid-market >and< enterprise at the same time. ARR per deal has gone up every quarter.

Coupa shows you can do both even in a complex offering, and has driven up ACVs in the mid-market in particular. You don't have to only go enterprise with a rich solution.
5. Slowly becoming a fintech.

Coupa isn’t as much a fintech as SMB players like Bill.com, but it’s getting there with Coupa Pay. Coupa plans the majority of its customers to be running payments through their platform in 10 years. Today, about 12% do.
A deeper dive here on Coupa at $700m ARR, growing a stunning 40% (!), here:

saastr.com/5-interesting-…
And a look back at how Coupa won here:

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More from @jasonlk

14 Sep
We're not grateful enough in venture -- including as founders:

- VCs are not grateful enough to those that source deals for them

- Founders are not grateful enough to early-stage VC that take real, big risks on them. Especially the ones they say No to.
- VCs are not grateful enough to co-investors that bail them out

- Founders are not grateful enough to VCs that bridge them and bail them out. They forget
- VCs are not grateful enough for the hard work that goes into each board meeting

- Founders are not grateful enough to that one VC that actually has their back at the board meeting. It's almost always just 1.
Read 7 tweets
10 Sep
I had a chance to catch up with René Lacerte, CEO of $27B+ @billcom this week

Bill has managed to build a $27B business selling to 120k SMBs

With an epic 125% NRR

My 10 learnings and our convo here: 🔽🔽🔽
#1. You can’t rush a network

Bill.com had to develop a network that today has millions on vendors processing bills and payments on it. But they couldn’t rush it. So they let folks use the platform the way they wanted, from paper checks to fax and more.
#2. You can’t always rush a fintech product.

It took a decade to come together. Rene cautioned folks to understand the regulatory & fraud elements of doing payments are significant. But it paid off.

Since IPO, payments have grown to a stunning 50% of Bill’s revenues
Read 12 tweets
7 Sep
When you start to hire your first sales reps, you'll hire some >good< people that still just fail and don't work out

That's on you to spot -- before you hire them:

Here are 9 reasons good salespeople fail: 🔽🔽🔽
#1. You hire sales reps that need lots of training, systems, and process in the early days

Big Companies, at least some of them, are generally very good at this. Larger, fast-growing start-ups often become excellent at it. Small start-ups are almost always terrible at it
#2. You hire a rep that hasn't sold at your price point before

Sales reps that are great at $20k deals join a start-up with tons of leads but at a $2k price point and fail again and again.

And vice-versa

Each price point has its own playbook
Read 11 tweets
6 Sep
Freshworks has just filed to IPO at $400,000,000 in ARR, growing an incredible 49% (!)

It's one of the first of a wave of India-U.S. global hybrid SaaS companies to IPO

5 Interesting Learnings: ⬇️⬇️⬇️⬇️⬇️
#1. A steady march above $5k in ACV

25% pay >$5k a year, but they represent 84% of ARR. That has gone up from 78% in 2019. Even with SMBs, it's bigger ones that are driving growth at scale

Going a smidge upmarket is key to Freshworks’ putting up the big numbers
#2. NRR of 118%.

This is pretty impressive for a mid-to-high ACV SMB sale, although pretty consistent with where Zendesk is today as well at 120%.
Read 9 tweets
28 Aug
It seems like everyone just explodes these days

But it's not really true

UiPath is worth $35B today and went from $1m to $30m ARR in just 24 months. Woah.

But ...

It took UiPath 10 years to get to the first $1m ARR

#latebloomers
More on UiPath here:

saastr.com/5-interesting-…
Similarly, Procore is worth $16B today but had a slow start

A slow first 10 years in fact until mobile really exploded

More here:

saastr.com/5-interesting-…
Read 4 tweets
17 Aug
I’ve interviewed 100s of VP of marketing candidates over years and I can tell you one thing — it’s >easy< to spot the ones that won’t work out

And yet, CEOs hire them again and again

Here are my Top 10 Interview Questions to make sure you don't hire the wrong VPM: ⬇️⬇️⬇️⬇️⬇️
1. What are the top 3 things you think we should upgrade in marketing?

This question tells you everything they will actually do

If demand gen isn’t in top 2 things to upgrade= — you don’t have a demand-gen focused VPM
2. What “commit” did you hold in your last roles? How much of it did you meet?

Great catch-all to see if have someone that can do demand gen. If they didn’t hold a real commit — in Opportunities, in Pipeline, Leads — they didn’t own anything that matters in revenue cycle
Read 13 tweets

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