SaaStr

JUNE 4, 2025

As a “prosumer” app there is overlap for SMB and freemium B2B apps. The 2021 fintech hype is mostly overpublic markets now reward fundamentals. So Chime is ready to IPO, and while it’s not SaaS or true B2B today, there are enough interesting lessons for us to learn from. Hit Profitability to IPO Chime hit $1.67

Outsourcing Services 201

Outsourcing Services Scale Banking Customer Lifetime Value 201

SaaStr

AUGUST 5, 2021

A great session for any founders and execs thinking about moving out of SMB and into larger deal sizes: She then became COO at rocketship, HubSpot, overseeing its incredible 50% year-over-year growth at $1.3B This is the age of the SMB in SaaS. Grew total customers to 121,048 at June 30, 2021, up 40% from June 30, 2020”.

SMB 341

SMB Scaling SaaS 341

SaaStr

DECEMBER 14, 2022

Yamini Rangan, CEO at HubSpot, has many insights on how to serve SMB customers at scale. The Challenge of Digital Expansion for SMB. When the shift began in 2020, everyone wrote off SMBs as unprepared for the necessary changes that lie ahead. By 2021, the market witnessed a frenzied phase to add point solutions.

Scale 261

Scale SMB Scaling Innovation 261

SaaStr

NOVEMBER 16, 2021

appeared first on SaaStr.

Scale 261

Scale Scaling SMB Revenue 261

SaaStr

DECEMBER 1, 2021

With two weeks left to go until SaaStr Scale 2021, we’re looking at an incredible speaker line-up this year. The post 5 Can’t Miss Sessions from SaaStr Scale 2021: Gorgias CEO, Box CRO, Asana COO + Figma CCO, Calendly CRO, Gitlab CEO appeared first on SaaStr. ” Sid Sijbrandij, CEO @ Gitlab. the DevOps platform.

Scale 278

Scale Scaling SMB compliance 278

SaaStr

AUGUST 30, 2021

Started 10 years ago as “Freshdesk” and a low-end / SMB helpdesk to rival Zendesk, Freshworks has since expanded its product footprint across IT management (Freshservice) and CRM (Freshsales) to a stunnning 49% growth rate at $350m in ARR. From 10,000 customers in 2015 to 50,000 in 2021. Headquartered in the U.S.,

Scale 361

Scale SMB Scaling Payment Features 361

SaaStr

JANUARY 13, 2022

Average NRR at IPO is 119% — but this excludes a bunch of SMB folks who did not disclose their NRR. Folks that are very SMB with mediocre retention often don’t disclose it. Only 33% of SaaS IPO’s in 2021 were HQ’d in the Bay Area. Squarespace’s NRR at IPO was only 85%. But still helpful to see.

SMB 360

SMB SaaS Retention Scale 360

SaaStr

MAY 7, 2021

. — Jason BeKind Lemkin (@jasonlk) May 6, 2021. HubSpot is sort a bell-weather stock and company for selling to SMBs and mid-market. And what we see is that SMB is on fire in SaaS. HubSpot is adding a breathtaking number of SMB customers at $1.1B And it shows the Best of Times for SMB SaaS have only just begun.

SMB 362

SMB Revenue Enterprise SaaS 362

SaaStr

JULY 27, 2022

If a SaaS business hopes to win over the SMB market successfully, it will need a precise GTM approach. Founded in 2015, PayFit is a software company that empowers entrepreneurs and SMBs to digitize payroll and HR processes. Boterri’s company Accel invested in PayFit in 2017 and again in 2021.

SMB 244

SMB Sales Hiring Scale B2C 244

SaaStr

JUNE 7, 2021

Find a way to fund both, even with SMBs. — Jason BeKind Lemkin (@jasonlk) June 7, 2021. If your SMB product requires or has a salesperson involved in closing, that’s a clear sign you also want a human being involved in making sure that customer is a success post-sale, too. The post Do SMBs Need Customer Success?

Customer Success 353

Customer Success Scale SMB Sales 353

SaaStr

APRIL 7, 2021

“SaaStr 416: The Secret Sauce for Scaling to $1B with Zendesk’s Sharon Prosser, VP Global SMB GTM and Ashta Malik, VP GTM Strategy “ A really terrific deep dive on selling and scaling to $1B in SMB ARR. #8. And how to win in a very competitive market. #7.

Scale 234

Scale SMB Churn Scaling 234

SaaStr

NOVEMBER 1, 2023

Well, fast forward to today and it’s truly an SMB powerhouse. How is SMB SaaS doing today? The rest of the growth is from its Divvy platform, which is bought in 2021 for $2.5 Most SMB-focused businesses need shorter CACs to make the model wok, but with 111% NRR, Bill can invest at > 12 months here. Bill is one.

Payment Services 339

Payment Services Payments SaaS Payments Payment Solutions 339

SaaStr

APRIL 13, 2021

— Jennifer Tejada (@jenntejada) January 8, 2021. It’s also an interesting contact to Zoom , Zendesk and Slack , which recently have seen enterprise and SMB growth be about equal post-Covid. #2. This is top-tier NRR for a product with many SMB customers. 95% renewal rate, even with 10,000+ SMBs.

SMB 329

SMB Enterprise Scaling Startup 329

SaaStr

APRIL 29, 2021

Shopify’s first quarter revenue: Q1 2021: $989 million Q1 2020: $470 million Q1 2019: $321 million Q1 2018: $214 million Q1 2017: $127 million Q1 2016: $73 million Q1 2015: $37 million Q1 2014: $19 million Q1 2013: $9 million. — Jon Erlichman (@JonErlichman) April 28, 2021. But Shopify is growing so fast — 110% a year (!)

Merchant Services 312

Merchant Services Payment Methods SaaS Payments Payments 312

SaaStr

JUNE 8, 2022

ARR, Zoom was an SMB powerhouse, with Enterprise growing. SMB is now saturated at $4B ARR and not growing, but Enterprise is picking up the slack and growing faster than ever. 100k+ customers are now the engine, not self-serve SMBs. Enterprise NRR is now 123%, but than means SMB is now well under 100%.

SMB 339

SMB Enterprise Engineering Scale 339

SaaStr

DECEMBER 12, 2023

Enterprise reps tend to close more ($1m+), and SMB reps less (maybe $500k), with $750k net new bookings per year the median. or so a year to take home those comp levels, and an SMB rep likely $800k or more. It all sounds a bit harsh at first — compared to the Go Go days of the 2021 or so. And how many hit quota?

Sales Hiring 334

Sales Hiring SMB Enterprise Metrics 334

SaaStr

FEBRUARY 19, 2022

— Jason BeKind Lemkin (@jasonlk) January 10, 2021. That journey here: Most of us don’t stay SMB forever. Zoom similarly started off almost 100% self-serve and SMB, and then later added an enterprise team. PagerDuty was almost entirely SMB at IPO, at $125m in ARR. Here’s why it usually happens.

SMB 341

SMB SaaS Enterprise Software 341

Nimble - Sales

JANUARY 22, 2021

The post How To Sell Software To Small Business: Successfully Selling SaaS to SMB in 2021 appeared first on Nimble Blog. For salespeople, things began looking worrisome pretty quickly. Specifically, for those […].

SMB 132

SMB Software Business SaaS 132

SaaStr

SEPTEMBER 16, 2022

Zoom’s SMB base has flattened after exploding like nothing we’ve ever seen before. Even if valuations aren’t what they were in the crazy times of 2021. And one of my themes was that while the markets are down, I mean way down — the best in SaaS are still growing at jaw-dropping rates. But go forth and conquer.

SMB 352

SMB SaaS Cloud Scaling 352

SaaStr

SEPTEMBER 9, 2021

Bill.com has become an SMB powerhouse, with 120,000+ customers and a stunning $25B+ market cap. But the accountant channel is high volume, SMB play. There are 6m SMBs that buy SaaS software. There are 6m customers out there just in SMB. That’s the magic in SMB SaaS. All while selling at a $2k ACV!

SaaS Payments 63

SaaS Payments Payments Payment Services Scale 63

SaaStr

MAY 21, 2021

— Jason BeKind Lemkin (@jasonlk) January 7, 2021. But Box became 95%+ enterprise by revenue over time, and Dropbox is still 95% SMB and smaller and consumer. But — Dropbox is much more of a consumer and SMB focused product. and keep you top of mind much more often. Let’s contrast Box and Dropbox. Few tweets.

Enterprise 339

Enterprise SMB Scaling Revenue 339

SaaStr

SEPTEMBER 22, 2022

So when we first started writing about Bill.com at its IPO , it was a sleep SMB accounting product. But yes, it’s the most incredible SMB growth story in SaaS we’ve ever seen. Up from 110% at IPO, 124% in 2021, and 121% in 2020. Don’t let anyone tell you it can’t be done with SMBs. #2. 131% NRR.

SaaS Payments 65

SaaS Payments Payment Solutions Payment Services Payments 65

SaaStr

APRIL 26, 2023

Having said that, many SMB players were hit hard in 2022. Zoom’s SMB customers shrunk for the first time ever, for example. Large mark-down for its $400m acquisition of Tock in 2021. Squarespace bought an online restaurant reservations player in 2021 for $400m, and that business continued. That’s very mature.

Scale 291

Scale SMB Churn Pricing 291

SaaStr

OCTOBER 22, 2021

119% NRR from SMBs!! — Jason BeKind Lemkin (@jasonlk) October 18, 2021. Still, 119% NRR from SMB is world-class even for 5+ seats accounts and sometime to strive for if you have similar sized customers. #4. but it’s growing from 9% in 2019 to 11% in 2021. An SMB sale, but less and less a single seat sale.

Scale 326

Scale SaaS Payments SMB Payment Solutions 326

SaaStr

MAY 10, 2023

And while that growth level is a bit off the crazy pace of 2021 , it’s still mighty impressive in the current macro environment. 23% Customer Count Growth Leads to 30% Revenue Growth, but NRR dips to 104% HubSpot is still very much SMB, especially the “M” of SMB. And what’s the latest?

Scale 322

Scale SMB Headcount New CTO 322

SaaStr

AUGUST 16, 2024

Andrew Bialecki, CEO Klaviyo This will be an epic deep dive on just how you get an SMB+ app to almost $1B in ARR — all while having incredibly happy customers. Klaviyo was the first SaaS company to IPO since 2021!! This will be a special one. And an epic one. #2.

CTO 307

CTO SMB AI SaaS 307

SaaStr

JANUARY 12, 2021

Most of the companies in this 5 Interesting Learnings Series have had net negative churn from SMBs (e.g., Xero’s SMB churn isn’t zero. — Xero (@Xero) January 11, 2021. It takes them over a year to go profitable on an SMB customer. — Jack Bremer (@jackbremer) January 11, 2021. And the U.K.

Customer Lifetime Value 283

Customer Lifetime Value SMB Churn Scale 283

SaaStr

NOVEMBER 15, 2022

It does less in SMB. Just not the Crazy Days of 2021. in ARR, so it’s second only to Salesforce in SaaS. And they spans dozens of leading vendors in SaaS. So Vista knows exactly what’s going on in SaaS buying now, especially enterprise and mid-market. That’s some slowdown for sure, but not a downturn.

Cybersecurity 354

Cybersecurity SMB Interviewing Enterprise 354

SaaStr

APRIL 13, 2023

And so many different strategies, from more enterprise to more SMB, from more tech focused (Asana) to less tech focused (Monday). Things are great at Asana, but still harder than it was at the peak of 2021 craziness as for most of us. In 2021, everyone was just buying everything. You can just learn so much.

SMB 305

SMB Outsourced Development Enterprise Scale 305

SaaStr

MAY 21, 2021

But then, growth became insane, rocketing from $1M in 2015 to $600M in 2021! Squarespace is self-service and SMB focused. It was founded in 2005 and took 10 years to get to $1m in ARR!! More on that here. Maybe the real point is that these 3 different software companies are so different.

Construction 341

Construction SMB Mobile Cloud 341

SaaStr

JULY 31, 2022

VC all seemed like a game in the boom times of 2021 and late 2020. The Challenge with SMB SaaS: High Growth Can Only Mask High Churn For Just So Long. SMB SaaS has a lot going for it, but one big existential challenge — inherent churn. 7 Secrets to a Successful SMB GTM Strategy with PayFit and Accel.

New CTO 300

New CTO CTO SMB Venture Capital 300

SaaStr

DECEMBER 19, 2021

In 2021, We Minted 46 Unicorns a Month. The State of Software Buying From SMB to Enterprise with G2’s CMO, Amanda Malko. Top Blog Posts This Week: 12 Things You’ll Look Back On in SaaS … And Regret. 5 Interesting Learnings from Samsara at $500,000,000 in ARR. The Average SaaS CEO is 43 at IPO. Top Video This Week: 1.

SMB 58

SMB Enterprise Customer Success Software 58

SaaStr

MARCH 10, 2024

Even SMB leaders like Monday are there. So folks aren’t in most cases literally working 2x harder than 2021. Not every individual will work twice as hard as 2021, but everyone together, has to be 2x as effective. The rest are marching there. Monday just crossed $800,000,000 in ARR with less than 2,000 employees.

SMB 293

SMB Cloud Startup Scaling 293

SaaStr

SEPTEMBER 1, 2023

The last SaaS leader to IPO was HashiCorp back in Dec 2021. 119% NRR from SMBs Profitable, and only burned $15m net to date 130,000 total customers There’s not much to not love here! But the metrics, especially for an SMB-focused SaaS business, are breathtaking. Getting above 100% NRR from true SMBs is tough.

Scale 283

Scale SMB Sales Hiring Interviewing 283

SaaStr

JULY 20, 2022

It IPO’d in November 2021 and today is doing $130m ARR, growing a respectable 30% year-over-year. While these aren’t great metrics if Weave was enterprise, they are still solid for SMBs. Many SMB SaaS companies struggle to hit 100% NRR and 80% GRR. A fairly standard SMB price point.

SaaS Payments 284

SaaS Payments Scale Payment Methods SMB 284

SaaStr

NOVEMBER 6, 2023

If you’re selling software to SMB merchants and outside of tech like Shopify and Toast and Monday , things are pretty, pretty good, if in some ways still harder than before. As compared to late 2020 and 2021, when change was the name of the game. So things are all over the place these days.

Merchant Services 307

Merchant Services Software Azure AWS 307

SaaStr

MAY 24, 2024

Yes, everyone has to be at least 2x as efficient as 2021, maybe more so. ARR: SMB leader HubSpot Enterprise vertical SaaS leader Veeva And collaboration leader DropBox All at the same ARR, but with very different growth profiles, and profitabilty. And the message to founders is confusing. But … that’s not enough.

SMB 307

SMB SaaS AI Scaling 307