SaaStr

MARCH 13, 2025

” It was the gold standard for B2B software companies scaling from $1M to $100M ARR. A deep dive with two leaders at the forefront of AI startup scaling and investment. Previously leading growth at Cohere and Heroku, he’s been instrumental in scaling multiple category-defining companies in the AI space.

AI 275

AI Scale Artificial Intelligence Startup 275

SaaStr

JANUARY 2, 2025

Have we lost interest in investing in the human side of sales? And in any sales-led motion, you are going to just need more sales reps year after year to scale. For the most part, folks seem done investing in more productivity for their sales humans. But the investment all around them in AI. It sort of seems like it.

Sales Hiring 330

Sales Hiring Scale Headcount AI 330

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

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 316

Venture Capital AI Scaling Investment 316

SaaStr

FEBRUARY 14, 2025

What does it take to build and scale a vertical SaaS giant over two decades? From surviving economic downturns to scaling into a multi-product enterprise serving millions, Procores story is a masterclass in vertical SaaS excellence. One challenge Procore faced in expansion was assuming brand awareness. In the U.S.,

Scale 287

Scale Construction SaaS AI 287

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 310

Scale SaaS Social Media Business Model 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 259

Sales Hiring AI Scale Compensation 259

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

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 262

Sales Hiring CTO Hire Scale Startup 262

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 327

Investment Scale Churn SaaS 327

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 294

Scale Sales Hiring Scaling Startup 294

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 310

SMB Payment Services Payments Payment Methods 310

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 262

Sales Hiring Scale Underperforming Technical Team Sales 262

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 312

Scale Sales Hiring Scaling Innovation 312

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 315

Scale Sales Hiring SaaS Payments Development 315

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 303

Scale Scaling Churn Investment 303

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 273

Churn Retention Scale Investment 273

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 304

Scaling Revenue Underperforming Technical Team Market Segmentation 304

SaaStr

MARCH 17, 2025

Im investing in fact at SaaStr Fund in a solo founder right now. These hires will define your companys DNA and help you scale faster [5][6]. Youll just need to be more deliberate about building a team that can help you scale and finding ways to stay sane along the way. Dear SaaStr: I Have No Co-Founder. What Should I Do?

Sales Hiring 249

Sales Hiring Scale Scaling Engineering 249

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 287

Scale Customer Success Scaling Revenue 287

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 262

Investment Compensation Startup Scaling 262

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 276

Venture Capital Investment CTO Churn 276

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 109

Scale Entrepreneurship Scaling Underperforming Technical Team 109

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 303

Scale Scaling Underperforming Technical Team User Experience 303

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 309

Scale Scaling Strategy Sales Hiring 309

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 285

B2B Investment Venture Capital Scale 285

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 238

Blockchain Merchant Services Payment Solutions Investment 238

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 263

Payment Solutions Inbound Sales Team Marketing Scale 263

SaaStr

OCTOBER 16, 2024

To set the stage, if you talk to any VC out there today, they will tell you that half of their investments which were growing at epic rates in 2021 are barely growing today. Salesforce is doing it, Zendesk and Intercom are all doing it at scale. Sorry, But There’s No Downturn. It’s already happening. Why is it growing so quickly?

Sales Hiring 320

Sales Hiring Scale AI SaaS 320

SaaStr

MARCH 8, 2025

But dilution is often the price of scaling. Series A and B investors want to control the ball and decide who invests more. If you invest at a $1B valuation, you worry about the downside. Is this the right advice? Seed investors worry about dilution. Their check sizes are relatively small. Is this best for the company?

Pricing 211

Pricing Investment Scaling Management 211

SaaStr

MARCH 9, 2025

The New AI ROI Framework Before investing in AI, Calendly’s team evaluates four key factors: Customer value (will this meaningfully improve outcomes?) As Shu concludes, “Gathering feedback early and often is crucial to making informed decisions about investments that yield returns for the customer.”

AI 205

AI Scale Education User Experience 205

SaaStr

SEPTEMBER 14, 2023

But with that out of the way, let’s talk just enough about financial accounting to explain why Big Tech Companies both acquire smaller ones — and do corporate VC investment. Because in the short-term, it often costs basically close to nothing to acquire a smaller startup with cash on hand, or do a corporate VC investment.

Acquisition 302

Acquisition Investment Headcount Banking 302

SaaStr

NOVEMBER 30, 2023

General Partner Doug Pepper and General Partner and Head of Analytics at ICONIQ Growth, Christine Edmonds, share the art and science of scaling GTM at this year’s SaaStr Annual. Early Growth Stage — $20M to $50M ARR This is the first time companies are really starting to build their GTM organizations for scale. What does that mean?

Scale 276

Scale Sales Hiring Scaling Outsourced Development 276

SaaStr

FEBRUARY 1, 2024

As companies scale, they evolve, so how should marketing evolve accordingly to add maximum value? PST, Kady shares the ten things that change in marketing as you scale. PST, Kady shares the ten things that change in marketing as you scale. The reality is that a lot of things change as we scale. The answer isn’t simple.

Scale 277

Scale Scaling Sales Hiring Marketing 277