SaaStr

JULY 5, 2025

SMB, mid-market, enterprise). Benchmark Your GRR : Investors will compare your GRR to industry standards: Enterprise SaaS: 90-95% Mid-market SaaS: 85-90% SMB SaaS: 80-85% Anything below these benchmarks signals potential retention issues ‌3‌. Segment by Customer Type : Break down GRR by customer segments (e.g.,

Retention 180

Retention SMB Benchmarks Churn 180

SaaStr

APRIL 28, 2025

Mid-Market Is The Perfect Laboratory For Both Product and Go-To-Market Development Most founders falsely view market segmentation as a binary choice between SMB and Enterprise. Yet they close in months, not years, with substantial ACVs ($20-70K+) that support full sales motions including SDRs, AEs, and CSMs.

Scale 260

Scale Transportation Scaling SMB 260

SaaStr

MARCH 23, 2021

Battery Ventures’ data says while VC investment $$$ are on fire — they aren’t going into more startups. The average SMB SaaS company has $295k in revenue per employee, and $450k in the enterprise. The post Battery Ventures: VC Investments Are Way Up. A few top takeaways: #1. ” #2.

Investment 316

Investment SMB Acquisition Cloud 316

SaaStr

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? While this title is SMB-oriented, the advice applies to Mid-Market and Enterprise, too. Lesson #2: Invest in Prospect Data Way Earlier So, now that you know what the customer looks like, you need to know how to target them. Invest way earlier than you think in prospect data.

Scale 301

Scale SMB Sales Hiring Sales 301

SaaStr

MAY 13, 2025

I got it wrong for a while too, until I started invest in and working with more vertical SaaS companies. New SMB customers often don’t already have a next-gen payroll platform in place. So this is a seemingly simple post, but it’s a point I find many founders, CROs, CMOs and more get wrong.

SMB 202

SMB Engineering Branding Investment 202

SaaStr

DECEMBER 1, 2021

You should also invest in building a community around your brand. Invest heavily in retention marketing. The post The State of Software Buying: From SMB to Enterprise with G2’s CMO appeared first on SaaStr. To help promote more customer-led content and reviews, treat your clients like your best marketing partners.

Software Review 284

Software Review SMB Enterprise Software 284

SaaStr

NOVEMBER 27, 2023

Having a predictable pipeline enables more effective decision-making, from headcount planning to strategic investments in technology and beyond. The post How Salesforce Runs Its Internal Forecasting Process with Salesforce’s VP Sales Strategy & Programs and RVP SMB Sales appeared first on SaaStr.

Forecasting 284

Forecasting SMB Sales Technical Review 284

SaaStr

NOVEMBER 27, 2024

Mangomint has worked hard to create an incentive structure that makes it attractive for sales reps to invest in customer success. And Mangomint invests a crazy amount into making sure its systems don’t go down since reliability and quality of product is so important for its customers. Those are two separate considerations.

SaaS Payments 257

SaaS Payments Payments Payment Solutions Payment Services 257

SaaStr

MAY 26, 2025

At least for SMB and more routine mid-market sales. Upskill Your Team : Invest in training that helps sales professionals collaborate effectively with AI systems. Organizations clinging to traditional sales structures especially in SMB and mid-marklet will find themselves rapidly outpaced by competitors embracing this hybrid approach.

Scale 239

Scale Sales Hiring AI Sales 239

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. The past few years have kicked off an unprecedented wave of digital expansion.

Scale 261

Scale SMB Scaling Innovation 261

SaaStr

JANUARY 23, 2025

But the rewards – higher retention, bigger deals, and ultimately a much larger TAM – make it worth the investment. Start Planning for Enterprise Earlier Than You Think The biggest mistake SaaS companies make? Waiting too long to start their enterprise planning. Your future self will thank you.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

JUNE 10, 2025

Many SMB SaaS companies with $20M ARR and decent growth get acquired for $100M+. Especially if your space is competitive and others are investing materially. You’re already in a good spot to compound growth steadily. That’s a great outcome if you’ve kept your cap table clean. The bar for venture capital is high, especially now.

Venture Capital 170

Venture Capital SMB Acquisition Churn 170

Clouded Judgement

JUNE 17, 2025

For businesses selling predominantly to SMB customers, these benchmarks are all slightly lower given the higher-churn nature of SMBs. I consider >120% best in class for companies selling to SMBs (like Bill.com). This is for information purposes and should not be construed as an investment recommendation.

Cloud 277

Cloud Software Benchmarks Retention 277

SaaStr

APRIL 1, 2023

How To Capture This Global SMBTech Opportunity There is massive market opportunity to sell to SMB businesses. Efficient Go To Market There are a lot of ways to GTM as an SMB. With SMB, you want hundreds or thousands of little merchants to pay you every month. One thing is for certain. That’s why patience is key.

Scale 245

Scale SMB Merchant Services Payment Methods 245

SaaStr

JANUARY 21, 2022

Dorian Stone , Head of Organizations Revenue at Grammarly, is here to share lessons from his experience of scaling the company from consumer to SMB to Enterprise to help you steer your expansion efforts in the right direction. The admin, influential decision-makers, and consumer sales reps can be the same people in a Consumer or SMB setting.

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. Boterri’s company Accel invested in PayFit in 2017 and again in 2021.

SMB 244

SMB Sales Hiring Scale B2C 244

SaaStr

MAY 28, 2025

The company is successfully evolving from its SMB roots into a serious enterprise software contender. The ability to maintain NDR above 110% at this scale from a still primarily SMB base proves their land-and-expand model continues to work effectively and customers find ongoing value in the platform.

Scale 192

Scale SMB Acquisition Enterprise 192

SaaStr

APRIL 14, 2025

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. And we’ve got an AI Demo Stage running all day, every day this year, right in the heart of Annual. 100+ scale-ups and start-ups showing you how they do it!

VP of Engineering 198

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 198

SaaStr

JUNE 4, 2025

As a “prosumer” app there is overlap for SMB and freemium B2B apps. Marketing Efficiency Improves With Product-Market Fit – Early Investment Pays Off Sales & marketing spend was ~$380 million in 2024, but efficiency has improvedmeasured by ARPU growth and profitability.

Outsourcing Services 201

Outsourcing Services Scale Banking Customer Lifetime Value 201

SaaStr

APRIL 30, 2025

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. But remember, this requires significant investment in product depth and breadth. Just above non-GAAP break-even (3% non-GAAP margins) 110% NRR and 95% GRR $10.5B

Payments 144

Payments Payment Services SaaS Payments Payment Solutions 144

SaaStr

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. Just assign a certain amount of ARR per each SMB customer success manager. Support has to handle a lot of routine SMB issues anyways.

Customer Success 353

Customer Success Scale SMB Sales 353

SaaStr

SEPTEMBER 7, 2024

So one of SaaStr Fund’s latest investments is Mangomint, a vertical SaaS platform for spas and salons. And yet, today Mangomint is at eight figures in ARR, growing 100%+, with 110% NRR from SMBs. Onboarding has to be much slicker for SMBs. Now … that sounds niche, and it sounds crowded.

SaaS Payments 312

SaaS Payments Payments Payment Methods SMB 312

SaaStr

JULY 14, 2022

Let me take a few example of the unicorns and decacorns I’ve been lucky enough to invest in. 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.

SMB 329

SMB Enterprise Government Startup 329

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. Over-invest in it. Go find them.

SaaS Payments 63

SaaS Payments Payment Services Payments Scale 63

SaaStr

NOVEMBER 12, 2020

Differentiating between Small and Medium Businesses (SMB) and Enterprise, or larger companies, is vital. You’ll need to find and hire different types of sales reps, specifically to sell into the Enterprise since enterprise sales are more challenging and typically take longer than selling into an SMB. 3 – Sustain.

Scale 293

Scale SMB Sales Hiring Enterprise readiness 293

SaaStr

FEBRUARY 24, 2021

Net net, even from SMBs, Upwork manages 100% NRR, just as Shopify and Hubspot do from SMBs. 80% SMB, 20% Enterprise. While Upwork has made inrounds into the enterprise, it remains squarely an SMB product. Upwork only now is looking at making deeper investments in a dedicated enterprise salesforce.

Marketplace as a Service 335

Marketplace as a Service SMB Cloud Enterprise 335

SaaStr

NOVEMBER 1, 2023

Well, fast forward to today and it’s truly an SMB powerhouse. How is SMB SaaS doing today? Most SMB-focused businesses need shorter CACs to make the model wok, but with 111% NRR, Bill can invest at > 12 months here. Billion in ARR, it’s still growing 48% year-over-year. Yes, 48% at $1.2 Billion in ARR.

Payment Services 339

Payment Services Payments SaaS Payments Payment Solutions 339

SaaStr

MAY 1, 2024

SMB Churn coming down, but still at SMB-Like Levels Zoom for years defied what we knew about SMB churn. It had 110%+ NRR from SMBs! But in the end, today, at scale, their small customers churn is at the same high rates as other “grab and go” SMB products. What a crazy story. to 3%, which is material.

SMB 299

SMB Scale Banking Churn 299

SaaStr

SEPTEMBER 2, 2023

This relationship is a rare example of increasing returns from investment in upsells and cross-sells. This is a rare example of increasing returns from investment in upsells and cross-sells. But, the best in SMB SaaS do tend to have higher NRR, especially as they scale. Invest wherever, however you can in increasing NRR.

Startup 293

Startup SaaS SMB Banking 293

SaaStr

SEPTEMBER 9, 2024

A third founder I funded at Owner, copied this format and I invested as well: 2 Cold Emails I Funded For Millions Finally he’s a great recent example of Mangomint, an SMB for the beauty industry. Just asking for coffee doesn’t. But here are two cold emails I funded for millions.

Software 299

Software SMB Banking Startup 299

SaaStr

MAY 4, 2025

Heres where I think its heading based on 100,000+ conversations already on SaaStr’s own AI , and my experience investing in so many contact center and post-sales leaders: 1. We Just Won’t Need as Many SMB Sales Reps. But 1 and 2 call closes for SMBs? And it’s just getting there in sales. The mid tier AEs?

AI 157

AI Scale Sales SMB 157

SaaStr

MARCH 28, 2025

Shopifys partner revenue grew from 8% in 2018 to 20% by 2020, but it took years of investment to get there . Treat your partner acquisition like a sales funneldefine stages, track progress in your CRM, and invest in partner enablement 3 7. Expect your sales cycle to double when working with partner s.

Scale 143

Scale Sales Hiring SMB Enterprise 143

SaaStr

NOVEMBER 15, 2022

It does less in SMB. Vista’s investments are older, established SaaS companies with brands. 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.

Cybersecurity 354

Cybersecurity SMB Interviewing Enterprise 354

SaaStr

OCTOBER 29, 2020

Zendesk doesn’t see the 140%+ net retention we see in the enterprise (big deal sizes) or in many B2D companies like Twilio, but it’s still above 110% for a business that is 60% Enterprise / 40% SMB. Strive for at least 110% net revenue retention if you sell to a mix of SMBs and Enterprise. Are you investing enough there?

SMB 290

SMB Enterprise Churn Retention 290

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. This is also how they can still afford to invest in a sales-driven sales process with such a low ACV. It takes them over a year to go profitable on an SMB customer. Churn is 1.1%

Customer Lifetime Value 283

Customer Lifetime Value SMB Churn Scale 283

SaaStr

DECEMBER 3, 2023

can invest in marketing that takes a little while to pay off). SMB SaaS often has much lower than 100% NRR, especially to start. Eventually most SaaS SMB leaders get to 100% NRR one way, or another (often by either going multiproduct and/or a bit more upmarket). But you can’t count that as profitable revenue. They don’t.

SaaS Payments 278

SaaS Payments Metrics SMB Payments 278

SaaStr

MARCH 28, 2025

SMB customers. For SMB SaaS, aim for 6 quarters of LTV:CAC, not 4 Ren adjusted the traditional benchmark because SMB customers stay longer than typically measured. Balance tech debt with innovation: Even after 18 years, Bill continues to invest in modernizing its platform while developing new capabilities.

SMB 130

SMB Payments Payment Services SaaS Payments 130