SaaStr

FEBRUARY 5, 2025

And when it IPO’d, it was still solidly an SMB solution. Leaning More into Free Even as it goes more enterprise, and see a decline in SMB / Commercial accounts, PagerDuty is still leaning in more on Free. We all used some sort of tool for website monitoring, but the O.G. As has PagerDuty. It’s efficient.

SMB 276

SMB B2B Enterprise Scale 276

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 184

Retention SMB Benchmarks Churn 184

SaaStr

DECEMBER 28, 2024

SMB-focused SaaS companies often have better performance with Facebook in particular, and can often deploy more there. And marketing, done well, on platforms almost always works. It’s hard to do well, but getting top placement on the Shopify ecosystem seems to work, for example. To a point.

B2B 261

B2B B2C Marketing SaaS 261

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

FastSpring

FEBRUARY 6, 2025

In this episode, we’re going to be talking about how SMB digital brands can win the best talent Joining us for that conversation is someone who knows quite a bit about that. The post How SMB Digital Brands Can Win the Best Talent appeared first on FastSpring. I’d like to welcome Lizzie Mintus.

SMB 108

SMB Sales Recruiting Branding Sales Hiring 108

SaaStr

JANUARY 9, 2025

Many that are self-serve and SMB-focused can start off without a sales team … for a while. Dear SaaStr: What Are Some Successful SaaS Leaders Without Sales Teams? But almost none stay without a sales team … forever. Yes, Atlassian since well past its IPO had almost no direct sales team.

Scale 274

Scale Sales Hiring Sales Headcount 274

SaaStr

JULY 11, 2025

Some can stay SMB only to $100m ARR, even $1B ARR. Going Upmarket: Many founders are reluctant to sell to larger customers, even when the opportunity is there. If you have customers willing to pay you $500/month instead of $5/month, you need to seriously consider going upmarket. And $5000 vs $500. But not most of us.

Scale 234

Scale Part-Time VPE Scaling Sales Hiring 234

SaaStr

JUNE 25, 2025

to dominate US SMB payments. TL;DR : After years of M&A drought, big deals are returning. It’s not just Wiz and Scale. In the latest billion+ acquisition, Xero just acquired Israeli-founded, NYC-based Melio for $2.5B revenue multiple proves strong B2B companies with real growth (and it’s strong) can still command premium exits.

Payments 224

Payments Payment Methods SaaS Payments Payment Solutions 224

SaaStr

JULY 9, 2025

If you’re in SMB or mid-market, keep in mind that CSMs can handle more accounts because the engagement tends to be lighter. As you scale and introduce automation or self-service tools, you can push closer to $2M per CSM, especially if your product becomes easier to manage or your team gets more efficient.

Customer Success 198

Customer Success Management Benchmarks SMB 198

SaaStr

JANUARY 3, 2025

In sales, t he more SMB you are, the more you should lean on your bench. With SMBs in particular, internal promotions can work better due to more “at-bats” and learning opportunities on the front lines. Lean into self-motivated talent.

Sales Hiring 284

Sales Hiring Scale Systems Review Interviewing 284

SaaStr

MAY 13, 2025

New SMB customers often don’t already have a next-gen payroll platform in place. They are SaaS for spas and salons. They were the first in their category to add payroll, and it’s gone well. But the attach rate for new customers is 50% higher than existing ones.

SMB 208

SMB Engineering Branding Investment 208

SaaStr

MAY 25, 2025

The 250,000 Customer Club: How HubSpot and Monday Both Created SMB+ Empires #4. How to build GTM Efficiency in SMB Sales Kyle Norton, CRO @ Owner.com #5. OpenAI to Hit $12.7 Billion in Revenue This Year. But Wont Be Profitable Until $125 Billion in Revenue #3. The Bar Today for a Series B #5. Top Pods and Vids: #1. For Real: Live

AI 242

AI SMB Revenue Startup 242

SaaStr

MAY 26, 2025

At least for SMB and more routine mid-market sales. Organizations clinging to traditional sales structures especially in SMB and mid-marklet will find themselves rapidly outpaced by competitors embracing this hybrid approach. But you can automate 30%-40% of support for real … with top 10% CSAT. A 50/50 Sales Team. 50% are AI.

Scale 245

Scale Sales Hiring AI Sales 245

SaaStr

NOVEMBER 27, 2024

a Month Churn especially SMB churn remains Zoom’s biggest challenge at its mature state, but it’s been pushing customers to annual and longer contracts and more. It’s dropped “Video” from its name as it has gone communications and AI-first: $4.7B And it still trades at 5x ARR. #1. a month, down from 3%. #2.

SMB 274

SMB Churn Enterprise Acquisition 274

SaaStr

JANUARY 8, 2025

The SMB sales team was incentivized purely on logo acquisition rather than revenue. Whereas in usage-based you have to be laser-focused on making sure that your customers are going live, adopting, and using the product as intended.” She explains: “Our smallest segment sales team was focused on activating customers.

Revenue 293

Revenue Scale Sales Hiring Compensation 293

SaaStr

JULY 18, 2025

Rough quotas of $500k for SMB, $700k for mid-market, and $1m for enterprise are fairly common and good rough guidelines. For example: If your goal is adding +$1m ARR this year, and you have 2 reps, each rep’s quota might be $500K in new ACV. Make sure quotas are realistic but challenging enough to push performance.

Scale 173

Scale Sales Compensation SMB 173

SaaStr

JUNE 17, 2025

Enterprise sales cycles will always be longer than SMB deals—it’s just the nature of the beast. Run Paid Pilots or Smaller Deployments : Offering opt-outs after 60-90 days or starting with smaller deployments can help prospects commit faster. Prove your value incrementally and build trust along the way. Show Up in Person.

Sales Hiring 173

Sales Hiring Enterprise Sales SMB 173

SaaStr

JANUARY 23, 2025

Start Planning for Enterprise Earlier Than You Think The biggest mistake SaaS companies make? Waiting too long to start their enterprise planning. ” 2.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

JUNE 9, 2025

For SMB sales, quotas closer to 3x OTE are common, while enterprise sales can push closer to 5x. Early Growth ($1M–$10M ARR): Once you’ve hit some traction, quotas should start aligning with your sales model. A good rule of thumb is to set quotas at 3x to 5x the rep’s fully burdened cost (their on-target earnings, or OTE).

Scale 173

Scale B2B Benchmarks Sales 173

SaaStr

NOVEMBER 27, 2024

How Much Time Should a CEO Be Involved With Customers When you have a high-velocity SMB motion that’s still sales-driven, how much time should the CEO spend in sales and with customers? And the more products they buy, the higher the NRR. Those are two separate considerations. Daniel talks to at least 5-10 customers every week.

SaaS Payments 257

SaaS Payments Payments Payment Solutions Payment Services 257

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. While ServiceTitan started as an SMB-focused platform, theyve steadily moved upmarket. 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 10, 2025

Many SMB SaaS companies with $20M ARR and decent growth get acquired for $100M+. You’re already in a good spot to compound growth steadily. If you can maintain 50% growth and keep churn low, you’ll likely hit $20M ARR or more in that timeframe, which is a sweet spot for strategic acquirers.

Venture Capital 173

Venture Capital SMB Acquisition Churn 173

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 197

Scale SMB Acquisition Enterprise 197

SaaStr

APRIL 14, 2025

AI Speakers: CEO Snowflake + CEO Observe: Where B2B Applications Are Going CEO Box Aaron Levie: AI, Agents and The Next Era of SaaS COO Google Cloud Francis deSouza: Hyperscalers: The Future and More CTO Rubrik: Co-Founder & CTO, Arvind Nithrakashyap CTO Neo4j: Philip Rathle (Valuation $2B+): How Revolut Left Salesforce and More: Rolling Your (..)

VP of Engineering 203

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 203

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 146

Strategy Payment Solutions Payment Methods SMB 146

SaaStr

JULY 18, 2025

The SMB Problem (And Opportunity) If your ACV is $50K+, this is solvable. The companies that figure out how to systematize this training process will win the SMB market. This is exactly what I was doing with our daily QA sessions. You hire Forward Deployed Engineers. They do the training. They handle the edge cases.

AI 198

AI Data Scale Artificial Intelligence 198

SaaStr

APRIL 2, 2025

Today it’s at: $800m ARR Growing 22% 20% Free Cash Flow Margins Modest re-acceleration in revenue growth and new customer count — but not NRR Roots are SMB, but 60% of ARR comes from mid-market and enterprise today And a $4B market cap, so 5x ARR Freshworks is getting a bit of a second wind, which is great to see!

Scale 270

Scale AI SMB B2B 270

Stax

JUNE 18, 2025

The most common challenges associated with vertical SaaS are competing for adoption against popular legacy or traditional SaaS solutions, a smaller lead pool that may soon exhaust, and managing the expectations of consumer-like SMB customers. Q: How can Vertical SaaS companies manage SMB customer expectations? What is Vertical SaaS?

Merchant Services 167

Merchant Services SaaS Payments Payment Services Payments 167

Tom Tunguz

FEBRUARY 26, 2025

Recent data from 2023 shows: The average startup saw a 24% increase in sales cycle length compared to early 2022 Enterprise-focused companies experienced a 36% increase, twice that of Mid-Market and SMB focused companies Usage-based companies suffered greater increases in sales cycle than seat-based companies: 29% vs 21% Enterprise-focused companies (..)

SaaS Payments 279

SaaS Payments Pricing Strategy Scale 279

SaaStr

JUNE 4, 2025

As a “prosumer” app there is overlap for SMB and freemium B2B apps. 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. products Non-GAAP Profitable (just), but profitability increasing quickly We’ll see where it trades.

Outsourcing Services 206

Outsourcing Services Scale Banking Customer Lifetime Value 206

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).

Cloud 277

Cloud Software Benchmarks Retention 277

SaaStr

JULY 23, 2025

Horizon 1: Individual Creators & SMB & Internal Apps (2025-2027) TAM: $2-12B This represents the current market: (1) individuals and small teams who need functional software, but lack technical resources or budget for custom development, (2) internal tools for more sophisticated tech teams, and (3) prototyping and proof-of-concept.

Software Review 193

Software Review Technical Review Development Team Review Systems Review 193

SaaStr

MARCH 21, 2025

It Takes Mobile Business Apps 222 Days to Hit $10,000 ACV An interesting remind for SMB and freemium apps … to earn it. But if they are using it and getting value, the RevenueCat data is a reminder to be patient here. It may even be better if they convert later, and get more value. #3.

Data 206

Data ChatGPT Mobile SMB 206

SaaStr

APRIL 12, 2025

For example: At Adobe Sign / EchoSign, we learned that SMB leads who hadnt used our product at least 3 times were far less likely to convert. Dont Convert Too Early Converting leads too early is a common mistake. If a lead hasnt been properly qualified, it will clog your pipeline and waste your sales teams time.

Systems Review 124

Systems Review SMB Engagement Sales 124

SaaStr

MAY 4, 2025

We Just Won’t Need as Many SMB Sales Reps. But 1 and 2 call closes for SMBs? At least, the best AEs. The mid tier AEs? We may or may not need them anymore (see next point). 2025 And The Rise of the Mech AE (Account Executive) 7. And VPs of Sales Will Need to Learn to Manage AIs Just as Much As Their Human Reps.

AI 157

AI Scale Sales SMB 157

SaaStr

MAY 18, 2025

A few ways to do it: Company Size (SMB, Mid-Market, Enterprise) : Splitting by company size almost always works once you have 2-3 sales reps hitting quota. SMBs often require a high-velocity sales motion, while enterprise deals are slower and more relationship-driven.

Scale 161

Scale Sales Healthcare SMB 161

SaaStr

APRIL 28, 2025

This will be particularly transformative for SMB-focused businesses doing high-volume, transactional deals. The AI knows every product detail, never oversells, tailors recommendations to company size, and can instantly close simple deals.

AI 243

AI Underperforming Technical Team Sales Technical Review 243