Jason ✨👾SaaStr.Ai✨ Lemkin Profile picture
Aug 21, 2021 8 tweets 3 min read Read on X
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

Jul 21
Vide Coding Day 11,

So today’s been a time of introspection and reflection. I have learned a lot becoming a ‘vibe coder’ and it has been addictive. For real.

My #1 learning is an old one, re-learned: Building Great Software is Still Hard.

Getting going is easier than ever. 🧵
On the dev tools side, I’ve asked all the best CTOs in my portfolio how much they really benefit from Cursor, Claude Code, et. al.

The consistent answer: net net, no one is giving back their Claude Code. No one. But net net, alone, it lets folks move about 20%-40% faster.

Why? These tools (all really Anthropic LLMs) help everyone do routine work faster, and in fact, some of the best devs I talk to can do 90% of most of their routine work in prompts.

But what about the hard stuff? The stuff that hasn’t been done before? The novel stuff?

What about the planning? The thinking?

What about code reviews and checking the work?

That all takes time.

So net net many are seeing a 20%-40% real productivity boost from Claude Code et. al. Much higher for routine stuff, but net net of all of the job — that’s where it seems to land today.
On the platform side, the B2C side, Replit+Loveable etc., this tools are magical. Magical. Maybe more than magical.

If you want to build a POC or prototype, it’s all magic, really.

But in the end, if you want to built true commercial grade apps, then they are … just tools.

Flawed tools, magical tools, but tools. At least today.

You can now think up an app and see it prototyped in < 20 minutes. Longer if you want all the buttons to work, but still.

But getting to >great< software? That’s in its own ways is hard as ever. Even if the tools are so much cooler, faster, and slicker.

No great engineers have been made obsolete here.
Read 6 tweets
Jul 18
Vibe Coding Day 9,

Yesterday was biggest roller coaster yet. I got out of bed early, excited to get back @Replit despite it constantly ignoring code freezes

By end of day, we rewrote core pages and made them much better

And then -- it deleted our production database. 🧵
You can read the thread here, and all the convos with @Replit. It went rogue again during a code freeze -- and deleted our >production< database.

Rule #00001 my CTO taught me: never, ever, never, ever touch the production database.

Even in 2005, when we launched the first version of EchoSign / Adobe Sign, everything broke. But the database was sacrosanct.

In 2025, 1 Billion+ contracts later, I think no contracts were ever lost in DB. A few corrupted, but none lost.

Yet, Replt went rogued and destroyed our production DB last night.

During a code freeze when it knew to touch nothing. And agreed to touch nothing.

x.com/jasonlk/status…
Now it gets a little crazier. Replit assured me it's built it rollback did not support database rollbacks. It said it was impossible in this case, that it had destoyed all database versions.

It turns out Replit was wrong, and the rollback did work. JFC.

Replit went rogue again, lied, and then said we couldn't roll back.

But we could. I'm still processing all this.

Is it OK there are NO guardrails to deleting a production database?

Why did Replit "lie"? Also, why did it not know about how this feature worked?

Look, no matter what, deleting a >production< database is NOT OK.

But Replit lied / was wrong, and I just rolled back. And it >seems< OK.

JFC though.Image
Read 12 tweets
Jul 17
Vibe Coding Day 8,

I'm not even out of bed yet and I'm already planning my day on @Replit.

Today is AI Day, to really add AI to our algo.

I'm excited. And yet ... yesterday was full of lies and deceit.
@Replit Ok I have 2 main goals today:

1. Keep working on minimizing rogue changes, lies, code overwrites, and making up fake data

2. Get our AI working Image
Now, yesterday was crazy. Until 9pm or so, I wasn't sure we made any progress at all.

Because Replie was lying and being deceptive all day. It kept covering up bugs and issues by creating fake data, fake reports, and worse of all, lying about our unit test.

We built detailed unit tests to test system performance. When the data came back and less than half were functioning, did Replie want to fix them?

No. Instead, it lied. It made up a report than almost all systems were working.

And it did it again and again.
Read 32 tweets
Jul 16
Vibe Coding Day 7,

Let me be clear about at least one thing: @Replit is the most addictive app I’ve ever used. At least since being a kid.

(@lovable_dev is great, too. We used it to build a core landing page. I’m not taking ‘sides’, but for this project, I chose Replit).

Last night I was thinking about vibe coding in the middle of the night. I checked on my app on my phone at dinner. And while I opened up the WSJ first this morning, my brain would have prefer Replit. I’ve dropped tons of other things to make more time to be with Replie.

Will I get there? Will I go from ideation to a 100% commercial-quality app all inside a vibe coding app? Without hiring a dev, coding myself, etc. etc.?

I don’t know. I give it a 50/50 shot right now. But I am … addicted. I need the hit.

In fact, I’m a totally different person than I was a week ago. @HarryStebbings said he saw it when my responsiveness plummet. I’m locked in.
The goal today: slow it down.

My biggest fear, and 100s of you have shared it yourself, is that vibe coded apps are never stable. That the AI keeps rewriting them when you think you’re about 50% of the way there.

I’m there, too. So my goal is to slow it down. Vibe Coding makes you feel like a superhero, but as cool as it is, I’m not SaaS Superman.

So today I am going to lock down as much of the app as I can. Research more on how to minimize rewrites. And really make sure my unit tests actually work.

If I spent all day on my unit and other tests, that would be good. Instead of instantly building new features :)
I spend $200+ yesterday on Replit and will likely spend that much today. When you go all-in, with Claude 4 and extended windows and GPUs blazing, it’s not $25/month.

It’s a little more than $1 a minute to use Replit in max/max mode. That’s “cheap” vs a human. But not “I built my own Notion for $2” cheap.

But I almost don’t care. I’m … addicted to vibe coding.
Read 12 tweets
Jul 9
🧵 We sent 4,495 AI SDR emails in 2 weeks and got the #1 response rate on our platform. Here's what actually works (and why 90% of companies fail at this):
First, the reality check: We have unfair advantages

SaaStr brand since 2012
Targeted our existing database (not cold lists)
Spent 2 weeks doing basically nothing else

If you're planning to blast cold prospects, your results will be very different. Image
The #1 mistake: Thinking you can "turn it on and walk away"

We spent 90 minutes every morning + 1 hour every evening training our AI. For 2 weeks straight.

You need to train AI like you'd train a human hire. Maybe more. Image
Read 13 tweets
Jun 29
So leading cross-over VC firm @coatuemgmt put out a detailed report on "The Great Separation" -- Who Wins, And Who Gets Left Behind, in the AI Age

My Top 10 Takeaways: 🧵 Image
#1: 2025 is the “Year of Offense” – Growth Trumps Everything -- Again

Coatue’s decision matrix for 2025 is brutally simple and reveals the new rules of the game:

🚀Growing >25% + Profitable? → Play offense aggressively
🐌Growing <25% + Profitable? → File your S1 immediately
🏰Growing >25% + Unprofitable? → Build fortress balance sheet
🔄 Growing <25% + Unprofitable? → Reinvent your business. ASAP.

👉Why This Matters: The window for going public with lower growth rates is wide open.

Public markets are rewarding ANY profitable growth right now. Companies that hesitate and wait for “perfect metrics” will miss the easiest IPO environment in years.

✅Action Items: If you’re profitable and growing, don’t wait.

If you’re unprofitable, get to breakeven fast or raise enough capital to survive the next wave. There’s no middle ground anymore.Image
#2: Growth Gets 13x Revenue Multiples vs 5x for Slow Growth – The Great Separation

The Math That Explains Everything

The valuation gap between fast and slow growers has never been wider:

🚀>25% Growth Companies: 13x revenue multiples (based on just 8 companies – that’s how rare they are)
🐌<25% Growth Companies: 4-5x revenue multiples (based on 163 companies)

🥇The Scarcity Factor: Only 5% of public software companies are growing >25% today, down from 26% in 2021

👉Historical Context:

We’ve gone from 17% median revenue growth (2021) to just 9% today. High-growth companies aren’t just getting premium valuations – they’re becoming unicorns in public markets.

🏃‍♀️The Brutal Reality:

Growth isn’t just valuable – it’s becoming extinct. If you’re growing fast, you’re literally in the top 5% of all software companies. Public markets are treating you like the rare asset you are.

✅Action Items:

If you’re growing >25%, leverage this scarcity for maximum valuation. If you’re growing <25%, understand you’re competing with 95% of the market for scraps.Image
Read 13 tweets

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