SaaStr

NOVEMBER 13, 2024

Klaviyo dominates marketing in the Shopify ecosystem and in ecommerce, and just keeps on scaling. But it’s clear that it’s still in the investing phase, and increasing spend in sales & marketing. So the latest SaaS leader to cross $1B ARR is Klaviyo. It was the only SaaS IPO on 2023. The only one!

Scale 306

Scale SMB Scaling Enterprise 306

SaaStr

MARCH 18, 2025

It’s an incredible look back on scaling and more: Colin Jones, first Chief Revenue Officer at Wiz. The result was a 5x increase over initial projections – growing from an $8M revenue target to $40M actual results – driven by a belief that market demand justified the investment.

Scale 189

Scale Sales Hiring Scaling Headcount 189

SaaStr

FEBRUARY 7, 2025

With Databricks now one of the largest pre-IPO technology companies, with $10 billion of expected non-dilutive financing and a valuation of $62 billion, Ron’s insights are gold for any revenue leader looking to scale. So we have a mix of both, but I think as we’ve scaled it’s become an advantage. ” The lesson?

Scale 182

Scale Sales Hiring Scaling Revenue 182

SaaStr

MARCH 14, 2023

Q: What are some common mistakes that investors make when evaluating potential startup investments (such as Seed or Series A)? A few I’ve made and watched others around me make: Invest in good traction with a pretty good but not great CEO. A so-so CEO with good traction usually … ends up not scaling to something all that big.

Investment 346

Investment Startup Scaling SaaS 346

SaaStr

OCTOBER 31, 2024

Here’s what I see most often, the Top 6 Mistakes First Time SaaS Founders Make: Incomplete understanding of business model, and how it will scale. But hiring folks that haven’t done it at all doesn’t scale past a few million in ARR. Basically I only invest in first-timers. VPs a Stretch Too Far.

Scale 312

Scale SaaS Social Media Business Model 312

SaaStr

SEPTEMBER 11, 2024

To do this, Lucid invested in a growth team tasked with iterating on all aspects of pricing, packaging, click pathing, and CTAs. It required Lucid to change its product, process, and overall user and administration systems to be able to scale with the customer. For Lucid, this meant a few things. Let’s look at Lucid’s timeline.

Scale 312

Scale Scaling Sales Hiring compliance 312

SaaStr

OCTOBER 13, 2024

I try to work with (and invest in) CEOs that are better than me. But now, I see that if you can hire a great COO as soon as possible after that, you can scale faster. is one of the top ways to help all of us scale faster. Dear SaaStr: Why did Jason M. they all failed or came up way short. and Management 2.0

Sales Hiring 263

Sales Hiring CTO Hire Scale Startup 263

Clouded Judgement

MARCH 28, 2025

Starting and scaling a software company was really hard. Starting and scaling a software company was really hard. If you wanted to scale users and growth, you needed to scale a physical data infrastructure footprint. ” This used to be how companies scaled! It wasn’t very elastic. What does this mean?

Cloud 299

Cloud AI Scale Scaling 299

SaaStr

MARCH 26, 2024

Since then, I’ve made some pretty good other investments as well. The top reasons an investment has turned out to be a Zero: #1. Or rather, it seems to work at first, but then it doesn’t really scale. ,,,,,… Now this sounds dramatic, and it is a bit dramatic, but the winners will more than balance out the losses.

Investment 328

Investment Scale Churn SaaS 328

SaaStr

MARCH 17, 2025

So we’ve all watched the mega VC rounds for OpenAI, Databricks, Anthropic etc as VCs deploy billions into the AI winners at scale. Massive investments, at massive valuations, into the biggest leaders of AI. At a scale we haven’t seen before. Far more than ever, per Redpoint’s latest data.

Venture Capital 315

Venture Capital AI Scaling Investment 315

SaaStr

AUGUST 9, 2024

From startup to $500M CARR, Spencer Burke, SVP of Growth at Braze, shares how Braze scaled a growth and customer success team. In this AI moment we’re in, there are still many moments in scaling a company where intuition still matters. You don’t have to leave as the organization scales. This isn’t new.

Scale 296

Scale Sales Hiring Scaling Startup 296

SaaStr

MAY 25, 2025

Its not about spending recklesslyits about having a cushion to make smart, accretive investments without worrying about running out of cash. If youre confident you might secure a higher valuation later, you could wait and raise at a larger scale. This is perhaps the #1 reason to raise capital you don’t strictly need.

Sales Hiring 239

Sales Hiring Scale Banking Scaling 239

SaaStr

OCTOBER 23, 2024

” Investing for growth has been pretty flat year over year for SMBs, which means there is money there, but they’re holding onto it. So at BILL’s scale, you have to put programs into place across the company to connect employees to customers, to help you focus on all the different stakeholders vs just the contract signer.

SMB 312

SMB Payment Services Payments Payment Methods 312

SaaStr

DECEMBER 20, 2024

Having led sales teams of 500+ at BILL and 800+ at HubSpot, Michelle has unique insights into what makes great frontline managers and why investing in them is crucial for sustainable growth. What’s great about high-volume sales at that scale is the pattern recognition,” Michelle shared. ” The bottom line?

Sales Hiring 263

Sales Hiring Scale Underperforming Technical Team Sales 263

SaaStr

AUGUST 15, 2024

There’s always someone a few years ahead of you on the scaling journey who can share their lessons learned. Robbie O’Connor, the GM EMEA at Notion and the first European hire at Asana and Dropbox takes the stage at SaaStr Europa to talk about the building blocks required to scale GTM teams and operations. Timing is also essential.

Scale 314

Scale Sales Hiring Scaling Innovation 314

SaaStr

MARCH 15, 2025

Its practical and relatable for SaaS founders struggling with scaling their sales teams. “ The Ultimate Guide to Scaling, Sales & Raising Capital.” “ The Ultimate Guide to Scaling, Sales & Raising Capital.” “10 Great Questions to Ask a VP Sales During an Interview.”

Sales Hiring 261

Sales Hiring AI Scale Compensation 261

Sales Hacker

NOVEMBER 29, 2024

Hello and welcome to The GTM Newsletter by GTMnow – read by 50,000+ revenue professionals weekly to stay up-to-date and scale their companies and careers. GTMfund’s 3 Areas of Focus for Investing Thanksgiving weekend is always a period of reflection and gratitude. We do invest in GTM software, but not that frequently.

Investment 113

Investment Technical Review Development Team Review Scale 113

SaaStr

JULY 11, 2024

There’s only a small chance that it’ll be an IPO exit, and Stacey Bishop with Scale Ventures shares what it takes to get to that next level of funding. To get VC to put money into your company, Scale Ventures looked at and calculated the minimum level of growth based on what typical venture investors require.

Scale 305

Scale Scaling Churn Investment 305

FastSpring

JANUARY 23, 2025

How selling an investment business is very different from getting VC funding. They’re interested in the return on investment, they’re interested in the growth opportunities, they’re interested in the strategies and the synergies that those businesses can bring them, either as individuals or as companies.

Scale 120

Scale Entrepreneurship Scaling Underperforming Technical Team 120

SaaStr

NOVEMBER 19, 2024

I see too few SaaS start-up and scale-ups truly segment churn. But I’d say 90% of SaaS companies I work with and have invested in don’t get these basics right for a long, long time. Because churn is the one thing everyone in the company can impact, on some level. Second, segment churn. Yes, a lot of this sounds basic. Not for real.

Churn 275

Churn Retention Scale Investment 275

SaaStr

MARCH 23, 2025

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. The 5 Key Elements of Codeium’s GTM Scaling Playbook 1. What is Codeium and Windsurf?

Sales Recruiting 245

Sales Recruiting Sales Hiring Scale AI 245

SaaStr

APRIL 5, 2025

But how did they scale so quickly? SEO: How Rupa Health Dominated Search with Programmatic SEO and AI Rupa Health invested heavily in search, aiming to own the top spots for specific lab tests and biomarkers. Its about creating high-quality content at scale. While paid acquisition can provide quick wins, it doesnt scale well.

Scale 231

Scale AI Search Sales Hiring Acquisition 231

SaaStr

MARCH 30, 2024

Dear SaaStr: What are The Most Common Mistakes Founders Make When They Are Just Starting to Scale Revenue? It’s one thing to invest in an area where only 5% of your business is today. As you scale, your win rate — the % of deals you close vs. the competition — should go down. More on that here: I Was Wrong.

Scaling 306

Scaling Revenue Underperforming Technical Team Market Segmentation 306

SaaStr

AUGUST 5, 2024

You have to show a return on investment, so this value narrative is essential to secure renewals and build those business cases to expand into existing customers and go after net new customers, too. What is the time investment so far in implementing the software and training the team to get where it is?

Scale 289

Scale Customer Success Scaling Revenue 289

SaaStr

MAY 25, 2024

Lesson #1: Invest In Customer Support Early Cloudinary strongly believes that customer success and support are enablers of PLG growth and aren’t just a cost center. They made a bet to hire a CFO early in their history to help guide them in terms of what the investment model should look like with PLG and, over time, with PLG and Enterprise.

Scale 316

Scale Sales Hiring SaaS Payments Development 316

SaaStr

OCTOBER 31, 2023

Dear SaaStr: What Did You Learn From Your Worst Venture Capital Investment? You can’t keep investing in the same companies, at the exact same stage, same valuations, etc. When I’ve cut a corner here and invested in startups with customers that aren’t super-happy, it hasn’t worked out as well. But the NPS/CSAT has to be there.

Venture Capital 278

Venture Capital Investment CTO Churn 278

SaaStr

JUNE 22, 2024

Dear SaaStr: Would You Invest in a Start-Up With 6 Co-Founders? The reality is, in most start-ups that have 4+ co-founders … several move on as you scale. UPDATED The post Dear SaaStr: Would You Invest in a Start-Up With 6 Co-Founders? I’ve done it — once. At least with 5 true co-founders. The downside? 6 is kind of impossible.

Investment 264

Investment Compensation Startup Scaling 264

Tom Tunguz

JULY 16, 2024

Large scale ETL (extract, transform, load) processes are a critical part of any data pipeline. How does a web3 analyst or product manager or consumer make sense of data at scale? We are thrilled to announce our investment in Allium , alongside friends at Amplify & Kleiner Perkins.

Blockchain 244

Blockchain Merchant Services Payment Solutions Investment 244

SaaStr

JUNE 19, 2024

Bitly CEO Toby Gabriner and CPO Kelsey Stevenson share the three secret ingredients that helped them when scaling to $100M ARR and what they could have done differently. The post The 3 Secret Ingredients for Scaling to $100M ARR with Bitly CEO and CPO appeared first on SaaStr. Lean into the risks and experiment.

Scale 306

Scale Scaling Underperforming Technical Team User Experience 306

SaaStr

DECEMBER 22, 2023

At the SaaStr Annual, Kiren Sekar, Samsara’s Chief Strategy Officer and founding chief Product Officer shared five lessons he learned along the way from scaling six products to $100M+. Lesson 1 — The Magic “Scale or Pivot” Metric With so many different SaaS metrics out there, which metric can really steer a business?

Scale 311

Scale Scaling Strategy Sales Hiring 311

SaaStr

DECEMBER 25, 2023

G2 had us back for another great deep dive on just where SaaS investing is there days, and it was a great panel: Accel Partner Arun Mathew Inspired Capital Founder & Managing Partner Alexa von Tobel Salesforce Ventures Managing Partner Paul Drews and Jason Lemkin! Low investment multiples pose a key challenge.

B2B 287

B2B Investment Venture Capital SaaS 287

SaaStr

FEBRUARY 7, 2025

At SaaStr AI Day 2025, Jim Palmer, Dialpad’s Chief AI Officer (and co-founder of TalkIQ, which Dialpad acquired), shared the tactical playbook they used to build and scale their AI capabilities. Here are the key learnings every SaaS company should know. Make this decision early.

AI 266

AI Scale Government compliance 266

SaaStr

MAY 10, 2025

GRR and logo retention are also critical, maybe even more so as you scale. Invest in Relationships Customer success isnt just about metricsits about people. Dont wait until youre at $5M or later to invest in customer success. Everything your team does should drive toward improving this number. Be careful here. Start Early.

Sales Hiring 235

Sales Hiring Customer Success Scale Retention 235

SaaStr

NOVEMBER 28, 2024

I try to look at two things in Vertical SaaS startups, at least when investing : Will everyone in the vertical / industry use it? It’s just hard to get most vertical SaaS start-ups to scale if they can’t get to a $10k ACV. Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS?

Payment Solutions 264

Payment Solutions Inbound Sales Team Marketing Scale 264