SaaStr

DECEMBER 1, 2021

B2B buyers are increasingly relying on their peers to make a purchase decision. The post The State of Software Buying: From SMB to Enterprise with G2’s CMO appeared first on SaaStr. This means that even if your website looks great and your product ranks high in a market research report, it’s not enough to convince most buyers.

Software Review 291

Software Review SMB Enterprise Software 291

SaaStr

JANUARY 21, 2022

If your organization is seeking growth in a new segment, like B2B—it will be a challenging ride because you’ll be in an unknown space. Now, let’s look at ten learnings that Dorian gathered while scaling Grammarly from a Consumer to an Enterprise brand with B2B offerings. Overview: Grammarly’s Enterprise Evolution.

Scale 246

Scale SMB Enterprise Sales Hiring 246

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. Without an autonomous-first approach, you will miss out on many SMBs.

SMB 244

SMB Sales Hiring Scale B2C 244

SaaStr

APRIL 28, 2025

What’s Changing in Sales: The AI Revolution is Here — and Coming Fast After analyzing 139,000+ conversations through SaaStr’s New AI, it’s now clear from the data: AI is about to fundamentally transform B2B sales. In B2B, the transformation will eliminate the frustrating experience of being bounced between departments.

AI 242

AI Underperforming Technical Team Sales Technical Review 242

SaaStr

APRIL 30, 2025

market cap (12x ARR) This is what a 12x ARR vertical B2B leader looks like today. Net Dollar Retention >110% and GDR of >95%: The Power of Being a True Operating System ServiceTitans NRR consistently exceeds 110%, even with SMB-heavy customers. Just above non-GAAP break-even (3% non-GAAP margins) 110% NRR and 95% GRR $10.5B

Payments 148

Payments Payment Services SaaS Payments Payment Solutions 148

SaaStr

APRIL 29, 2025

250+ speakers. 12,000+ SaaS leaders. 100B+ in market cap. 250+ speakers. 12,000+ SaaS leaders. 100B+ in market cap.

AI Search 163

AI Search AI New CTO Scale 163

SaaStr

OCTOBER 3, 2023

PST, Bo Borland, founder, and CEO of playbuilt, shares four steps for creating repeatable success at every stage of growth, specifically in B2B Enterprise. Let’s look at Borland’s approach to aligning and executing B2B team selling motions for a rinse-and-repeat process for growth. Mapping 9-box to the buyer’s journey and team roles.

Enterprise 298

Enterprise B2B Scale SMB 298

SaaStr

MAY 24, 2025

Top 10 Strategies Toasts CRO Uses to Crush Sales Quotas So a little while ago Toasts CRO Jonathan Vassil joined Sam Blond on SaaStr CRO Confidential on how Toast built one of the strongest but toughest rocketship in sales: a lower gross margin, lower ACV ($10k), sales-led SMB sales motion. Even with SMB Sales. Field-Based Sales Model.

Strategy 144

Strategy Payment Solutions Payment Methods SMB 144

SaaStr

AUGUST 16, 2024

So we’re pretty lucky this year, we’ve got some of the top leaders in B2B ecommerce at SaaStr Annual, Sep 10-12 in SF Bay! #1. 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. This will be a special one.

CTO 313

CTO SMB AI B2B 313

SaaStr

MAY 10, 2023

They’re a barometer of sub-enterprise B2B SaaS in many ways. 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. This is a similar dynamic to Shopify but one many SMB leaders have not cracked.

Scale 325

Scale SMB Headcount New CTO 325

SaaStr

DECEMBER 27, 2023

For B2B Generative AI Apps, is Less More? 10 Learnings on High Velocity Sales to SMB with Gorgias’ CEO and VPS Gorgias has 13,000 SMB customers. 10 Learnings on High Velocity Sales to SMB with Gorgias’ CEO and VPS Gorgias has 13,000 SMB customers. A very tactical guide to scaling SMB sales. #7. Harness.io

Scale 290

Scale SMB Generative AI AI 290

SaaStr

OCTOBER 26, 2021

In a noisy world where there are no practical barriers to creating B2B content, you need a thoughtful approach to engage your Ideal Customer Profile audience. . Marketing SaaStr Session #1: “The State of Software Buying: From SMB to Enterprise with G2’s CMO”.

Scale 358

Scale Marketing SMB Leadership 358

SaaStr

JULY 28, 2020

RingCentral went from SMB to enterprise-grade contact center. Zoom used to be a B2B app ??. Veeva added an entire, larger second product. Twilio expanded into contact center and email and more. Shopify added a wildly successful enterprise offering. The Era of the SaaS Decacorn is Here.

SaaS 363

SaaS SMB Cloud Enterprise 363

SaaStr

MAY 3, 2023

Freshworks is doing a lot of things right in a challenging time for many “traditional” B2B segments like CRM, Support, etc. NRR Still Impressive at 107% Given Many SMB Customers, Although Down Year-over-Year from 115%. it’s harder for many in B2B in Europe. #4. — so a great one to learn from!

SMB 329

SMB B2B Revenue SaaS 329

SaaStr

FEBRUARY 13, 2025

So there are two massively different vibes in B2B and Cloud and SaaS today: Folks fighting to keep slowing growth going. Not just for consumer and SMB. Which, perhaps ironically, leads vendors to be less customer-centric. but also In high-growth AI-fueled spaces, massive competition as well. Free and Freemium are back.

AI 209

AI ChatGPT SMB Enterprise 209

SaaStr

SEPTEMBER 2, 2023

Figure 5 comes from our 2023 SaaS Retention Benchmarks for Private B2B Companies and highlights the relationship between growth and retention. First, SMB SaaS almost always has lower NRR, especially in the earlier years, and that hasn’t stopped HubSpot and Toast many others from getting mighty big. But the data is real.

Startup 300

Startup SaaS SMB Banking 300

SaaStr

JUNE 17, 2019

And the average SMB buyer has already purchased 50+ apps. The post What is the psychology behind the B2B enterprise sale? In 2019, the average enterprise buyers has deployed over 100+ SaaS apps, per Okta numbers. So your prospects and customers are veterans. The general pyschology thus is different than it used to be in SaaS.

Enterprise 183

Enterprise B2B Sales SMB 183

SaaStr

JULY 14, 2022

Talkdesk, last valued at $10B, started off as an SMB Zendesk and Salesforce plug in at a $25m valuation when I first invested. That’s a big change from a grab-and-go SMB solution in the early days. As a side note, SMB SaaS companies often hit TTAM issues earlier.

SMB 332

SMB Enterprise Government compliance 332

SaaStr

DECEMBER 3, 2023

But what’s clear is it’s a terrible, terrible idea in B2B and SaaS to include 0%-10% gross margin pass-through revenue when you model your SaaS metrics. SMB SaaS often has much lower than 100% NRR, especially to start. Loss-making Hardware Revenue Doesn’t Count. Toast loses money on those cool devices you use in restaurants.

SaaS Payments 285

SaaS Payments Metrics SMB Payments 285

SaaStr

JUNE 29, 2022

It’s moved beyond its tiniest customers, of an ACV of < $1k, but other than that, it’s going upmarket without giving up its SMB roots. Even though Zendesk still has thousands and thousands of SMB customers. #2. Zendesk IPO’d as an SMB support solution. Run toward, not away, from global expansion in B2B. #9.

SMB 300

SMB Scale B2B Revenue 300

SaaStr

MARCH 6, 2024

But it’s also tied to B2B seat models and tech. So as tech companies tighter their belts, and decrease seats, the same headwinds that have impacted ZoomInfo, Zoom, and many B2B leaders from Outreach to Gong and more also impact Okta. Cloudflare, Zscaler, Wiz, and so many more are on fire today.

Fractional VPE 288

Fractional VPE Part-Time VPE Scale SMB 288

SaaStr

NOVEMBER 2, 2022

The core product is very B2C, but the upgrade to paid has very SMB B2B metrics, and 80% of the revenue is subscription based. A/B testing can be harder in lower volume B2B products, but it’s a reminder we all need to do more of it. So it’s doing what Wall Street wants today. But is Duolingo SaaS?

Scale 322

Scale B2C SMB B2B 322

SaaStr

DECEMBER 31, 2022

The 4 V’s of Sales: Volume, Value, and Velocity: Waze Head of SMB Sales & Head of Sales Enablement. A good and different look at some good ideas for SMB sales. #6. 10. “SaaStr Annual 2022: 5 Critical and Company-Altering Learnings from B2B Startups | Y Combinator.”

Scale 246

Scale SMB Innovation B2B 246

SaaStr

APRIL 30, 2021

Top-tier for B2B enterprise software. A solid yardstick for a product that is 50/50 enterprise and SMB, with a great Free edition. Smartsheet’s NRR is 123% from SMBs. This is probably about as good as it gets for SMBs. Some best-of-breed examples: Snowflake’s NRR is 162%. UiPath’s NRR is 145%.

SMB 326

SMB Benchmarks Enterprise B2B 326

SaaStr

JUNE 22, 2023

B2B folks want to do B2C. SMB folks want to go upmarket because there is too much churn in SMB. . – SaaStr Trying to pursue a “Grass is Greener” business model. Enterprise folks want to do freemium because they think it is easier. That’s OK, but pretty risky. 85 times out of 100 — do what you know.

SMB 279

SMB SaaS B2C Interviewing 279

SaaStr

DECEMBER 27, 2020

Those of us who’ve been around a while think of New Relic as a freemium and almost SMB tool, but today 77% of their revenue comes from accounts greater than $100k. I’ve seen this across other B2B/API companies I’ve invested in. The multiples just don’t support it.

Scale 342

Scale Outsourced Development SMB Cloud 342

SaaStr

MAY 18, 2022

But most B2B products aren’t that easy to use. Even SMB leaders like Monday waited to go Freemium. For sure this is part of most Freemium products we all use every day, from Canva to Zoom to Notion to Spotify. More on that here.

SMB 290

SMB Pricing B2B Engineering 290

SaaStr

JULY 27, 2019

But this is way too complex and downstream a metric for SMB sales and higher volumes of qualified leads. The post In B2B marketing, how do I get sales and marketing to work together? This really only works as the #1 core metric for marketing IMHO and experience if you are only doing $50k-$100k+ deals or bigger, roughly.

B2B 182

B2B Marketing Sales Social Media 182

SaaStr

SEPTEMBER 1, 2023

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. 130,000 Customers, So About $5,000 on Average A Year Per Customer.

Scale 290

Scale SMB Sales Hiring Interviewing 290

SaaStr

APRIL 10, 2023

B2B SaaS companies often aim to land large enterprise clients that can bring with them long relationships and large deals. Others may seek to corner the SMB market. Zendesk knew that they could risk selling to startups like any other SMB, so that was the problem they set out to solve.

Startup 276

Startup Scale SMB Venture Capital 276

SaaStr

JUNE 3, 2023

So it’s really probably easier if you start in freemium, SMB, consumer, or developer tools. So … it would make sense 34 is a decent average starting point, especially in B2B that sells to bigger customers. Dylan Field was already known as the top intern ever at Flipboard when he worked there. But less so in enterprise software.

Software Review 240

Software Review SMB Enterprise B2B 240

Aaron Beashel

MARCH 9, 2018

In the case of a B2B SaaS company, your Go To Market model outlines the way in which you acquire customers. The end users of their software are marketers at SMB companies and they sell their product for around $100 per month (Meaning the Annual Contact Value is around $1000). What is a Go To Market model? Business Resources.

Scale 192

Scale SaaS Payments B2B Strategy 192

Sales Hacker

FEBRUARY 14, 2022

They sit around a table and share actionable insights about their company’s transition from SMB to enterprise sales. . Why they restructured their B2B sales team into three key verticals. There’s one nightmare scenario every company wants to avoid when they make the transition from SMB to Enterprise. Mid-market. Enterprise. “In

SMB 106

SMB Enterprise Scale Outbound Sales Team 106

Sales Hacker

JANUARY 9, 2023

My first day in B2B sales, I onboarded with an account executive who was part of my new company’s enterprise sales team. Related: How to Transition from SMB to Enterprise: Tips from 3 Experts. SMB, mid-market, and enterprise defined. SMB, mid-market, and enterprise defined. Selling to SMB. Table of contents.

SMB 103

SMB Scale Enterprise Sales 103

SaaStr

JULY 1, 2024

Right now, you may have 3-4-stage sales processes that work for SMB customers. Hopefully, you’ve built a partnership ecosystem for SMB customers, but it’s probably a completely different strategy for what you need to go upmarket for a couple of reasons. So, find sellers inside your sales org who can at least get you started.

Sales Hiring 306

Sales Hiring Scale SMB compliance 306

SaaStr

OCTOBER 5, 2022

Especially if you are a B2B app not limited by regulations like a lot of fintech and others are. And a lot of thing they are really something more enterprise than SMB. International Customers Are > 50% of Business. We’ve discussed this many times on SaaStr, but going global early can be a great accelerant to growth.

Scale 291

Scale SMB Scaling B2B 291

SaaStr

FEBRUARY 14, 2024

But that’s not the way B2B businesses work. One thing that has positively changed for customer success, especially for the SMB-focused, is far larger onboarding teams. This is great news because onboarding is one of the best ways to bring down churn for SMBs. There’s not a lot of oxygen left for maintaining customers.

Customer Success 305

Customer Success Sales Hiring Scale Headcount 305