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 176

Scale Sales Hiring Scaling Revenue 176

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 307

Scale SaaS Social Media Business Model 307

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 307

Scale Scaling Sales Hiring compliance 307

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

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 260

Sales Hiring CTO Hire Scale Startup 260

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

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 325

Investment Scale Churn SaaS 325

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 291

Scale Sales Hiring Scaling Startup 291

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 307

SMB Payment Services Payments Payment Methods 307

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 260

Sales Hiring Scale Underperforming Technical Team Sales 260

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 310

Scale Sales Hiring Scaling Innovation 310

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 258

Sales Hiring AI Scale Compensation 258

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

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 312

Scale Sales Hiring SaaS Payments Development 312

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

Tom Tunguz

DECEMBER 26, 2022

A former venture capitalist, Mark Leonard started Constellation in 1995 with $15m of outside investment & a goal of buying vertical software companies with a moat & good unit economics. But at scale, software holding companies can grow at similar rates & trade at similar multiples to their venture-backed peers. BU Size. #

Software Review 295

Software Review Investment Software Acquisition 295

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 300

Scale Scaling Churn Investment 300

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 270

Churn Retention Scale Investment 270

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 242

Sales Recruiting Sales Hiring Scale AI 242

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 229

Scale AI Search Sales Hiring Acquisition 229

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 301

Scaling Revenue Underperforming Technical Team Market Segmentation 301

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 284

Scale Customer Success Scaling Revenue 284

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 261

Investment Compensation Startup Scaling 261

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 243

Blockchain Merchant Services Payment Solutions Investment 243

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 273

Venture Capital Investment CTO Churn 273

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 300

Scale Scaling Underperforming Technical Team User Experience 300

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 306

Scale Scaling Strategy Sales Hiring 306

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 214

Sales Hiring Customer Success Scale Retention 214

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 282

B2B Investment Venture Capital Scale 282

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 262

AI Scale Government compliance 262

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 261

Payment Solutions Inbound Sales Team Marketing Scale 261

SaaStr

APRIL 30, 2025

ServiceTitan, the operating system for the trades, continues to scale impressively, with $772M in FY25 revenue, $800m+ ARR and a clear path to $1B ARR. But remember, this requires significant investment in product depth and breadth. This shift has been critical to scaling beyond $500M ARR. Accelerating at Scale.

Payments 144

Payments Payment Services SaaS Payments Payment Solutions 144

SaaStr

APRIL 14, 2025

100+ scale-ups and start-ups showing you how they do it! 800+ VCs Ready to Invest This year, were bringing together over 800 VCs and investors, making SaaStr Annual 2025 the ultimate place to pitch, connect, and secure funding. If youre serious about scaling software, you cant afford to miss it.

VP of Engineering 204

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 204