SaaStr

MAY 28, 2025

The company is successfully evolving from its SMB roots into a serious enterprise software contender. With $110M in adjusted free cash flow this quarter alone, they’ve positioned themselves with significant capital to reinvest in growth opportunities, potentially including strategic acquisitions to expand their platform capabilities.

Scale 197

Scale SMB Acquisition Enterprise 197

SaaStr

JUNE 10, 2025

If you want to aim for a strategic acquisition in 5 years, staying bootstrapped or lightly capitalized is probably better. 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 growth slows, raising again or exiting at a high multiple gets harder.

Venture Capital 173

Venture Capital SMB Acquisition Churn 173

SaaStr

JUNE 4, 2025

As a “prosumer” app there is overlap for SMB and freemium B2B apps. Referrals are Chime’s largest acquisition driver since 2022 , helping bring sales & marketing spend down to 26% of revenue in Q1 2025, from 42% in 2022. But if it lands around $9 Billion, that’s less than 5x revenues. million in Q1 2025.

Outsourcing Services 206

Outsourcing Services Scale Banking Customer Lifetime Value 206

SaaStr

JUNE 9, 2025

For SMB sales, quotas closer to 3x OTE are common, while enterprise sales can push closer to 5x. You might also shift from focusing solely on revenue to incorporating metrics like logo acquisition or customer retention. Early Growth ($1M–$10M ARR): Once you’ve hit some traction, quotas should start aligning with your sales model.

Scale 173

Scale B2B Benchmarks Sales 173

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

Sales Hacker

DECEMBER 17, 2024

The post GTM 126: Reverse Engineering the Founder Journey: From Scaling Twitter Ads to $650M, 20 Years Operating, and a Webflow Acquisition | Guy Yalif appeared first on GTMnow. Scott Barker: [26:53] Did you go about shifting that so how were what were some of the strategies you used to shift um how the market was perceiving you.

Scale 101

Scale Engineering Acquisition Scaling 101

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. This increases conversions and ROI and lowers the customer acquisition cost.

Merchant Services 167

Merchant Services SaaS Payments Payment Services Payments 167

Tom Tunguz

FEBRUARY 26, 2025

Just a quick reminder: Payback Period = Cost of Customer Acquisition/Gross Margin The gross margin is the revenue per customer minus the costs to provide the service. A decrease in price reduces gross margin and will consequently increase payback period.

SaaS Payments 279

SaaS Payments Pricing Strategy Scale 279

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

MARCH 28, 2025

Treat your partner acquisition like a sales funneldefine stages, track progress in your CRM, and invest in partner enablement 3 7. More here: 7 Thoughts on Building Your First Partner Program And how Gorgias got to 10,000+ SMB customers with partners here: Focus on High-Impact Partners Not all partners are created equal.

Scale 146

Scale Sales Hiring SMB Enterprise 146

Payrix

JANUARY 28, 2025

Mergers, acquisitions, and IPOs : With the resurgence of M&A activity and an opening IPO market, software companies can explore opportunities for consolidation and value creation. That could be brand, that could be how the SMB interacts with the consumer. And some might say, quote, unquote, controlling the experience.

Payments 130

Payments Payment Solutions Merchant Services Payment Methods 130

How To Buy Saas

FEBRUARY 25, 2025

Through numerous acquisitions (ExactTarget, Tableau, Slack, and more), Salesforce built an expansive ecosystem of cloud services. Rapid SMB adoption with 200K+ customers. Startups, SMBs, and mid-market; teams wanting all-in-one marketing + sales. In fact, many user reviews and consultants will point an SMB to HubSpot first.

Scale 52

Scale Underperforming Technical Team Technical Review Marketplace as a Service 52

User Pilot

JULY 17, 2025

Many product teams focus on new customer acquisition but ignore the cost of losing customers they’ve already paid to acquire. With customer acquisition costs rising and retention driving most of your customer lifetime value, ignoring churn is a fast track to stalled growth. Industry benchmarks show: SMB SaaS: 5-7% monthly churn.

Churn 85

Churn SaaS Payments Payment Solutions Underperforming Technical Team 85

How To Buy Saas

MAY 21, 2025

Whether youre a startup , an SMB , or a global enterprise , the right ATS can streamline your recruitment process, save time, and help attract top talent in a competitive market. Its tailored more to SMB use cases. Scaling Limits: For an SMB-focused tool, VIVAHR works brilliantly. complex analytics or deep CRM capabilities).

Systems Review 52

Systems Review Sales Recruiting Sales Hiring Technical Review 52

Chart Mogul

DECEMBER 12, 2024

Success will rely on mastering distribution and customer acquisition. With advances in AI, automation and workflow integrations, ABM will be available to even small teams going after SMB and mid-market sized deals. With countless AI-driven clones flooding the market, product differentiation won’t be enough.

Fractional VPE 40

Fractional VPE Software Review SaaS Part-Time VPE 40

Sales Hacker

APRIL 8, 2025

Prior to Carta, Jeff led SMB Sales at DocuSign, and started his career at Oracle, where he rose from Strategic Account Manager to VP of Sales over a decade. 12:42 Lessons from selling servers that still apply to modern SaaS sales 15:02 Leading through M&A: Inside the culture clash and how Jeff rebuilt a team post-acquisition.

Scale 66

Scale Sales Hiring Scaling Revenue 66

Sales Hacker

APRIL 1, 2025

The exact playbook to move from SMB to enterpriseincluding partner enablement, segmentation, and incentive design. 85% of your customers being SMB and mid-market to at the end of that six years, it was 75%, uh, enterprise. Why retention isn’t just a CS metricand how to build a sales team that cares about it.

Scale 62

Scale VP of Engineering Outsourcing Services Enterprise 62

Sales Hacker

FEBRUARY 25, 2025

Obviously, SMB, smaller companies, there’s risk when the market’s the way it is. You are directly contributing to how a product is being built, pricing impacts, all of these things influence the entire, you know, org and that’s, what’s going to, you know, drive up the acquisition price or, or make it more.

Sales Hiring 80

Sales Hiring Marketing Technical Review Sales Recruiting 80

SaaStr

APRIL 1, 2025

Wiz: Territory Matters More Than Tech Stack Colin Yasukochi (Wiz CRO) demonstrated that even on the path to a $32B acquisition, territory design was more impactful than AI tools. This created almost opposite playbooks for their SMB vs. enterprise motions, complicating their enablement strategy.

Scale 207

Scale Sales Hiring Underperforming Technical Team Headcount 207

Sales Hacker

JULY 8, 2025

Love to hear you know a little bit around that experience of going through that acquisition and joining LinkedIn and how that experience was for you. 19:43 And just the way that he thinks about acquisitions and sales LinkedIn, you know, did obviously some acquisitions. 42:41 Why SDRs won’t disappear — but their job will change.

Sales Recruiting 79

Sales Recruiting Sales Hiring AI Search Scale 79

SaaStr

JULY 10, 2025

But Toast went a more “SMB” route focusing on smaller restaurants and chains. larger revenue base by 2025. Sometimes the bigger market wins, even with lower initial margins. When are smaller customers “better”? Olo was just acquired for $2B by Thoma Bravo after 20 years — a big success. That’s lead to a $25B market cap today. 10x larger.

Technical Review 173

Technical Review Payments Scale Payment Solutions 173

Sales Hacker

JANUARY 13, 2025

Each segment, whether SMB, mid-market, or enterprise, has its own nuances, but they all share a familiar core. To scale this support and extend it beyond our portfolio to the broader SaaS ecosystem, weve partnered with Pursuit – a leader in go-to-market talent acquisition. Culture becomes the engine.

Scale 106

Scale Sales Hiring Artificial Intelligence SMB 106

SaaStr

MARCH 30, 2025

Co-founders Dharmesh Shah (CTO) and Brian Halligan (Chairperson) shared at SaaStr Annual the unfiltered truth on building an SMB powerhouse, pivoting to product-led growth, and why the “M” segment is SaaS gold. The SMB market offered a sweet spot between enterprise complexity and consumer scale.

Scale 193

Scale SMB Sales Hiring Scaling 193

SaaStr

DECEMBER 1, 2021

Many marketing departments get too focused on customer acquisition but forget to market to the customers they already have. . The post The State of Software Buying: From SMB to Enterprise with G2’s CMO appeared first on SaaStr. Invest heavily in retention marketing. You’ll also want to monitor churn risk closely.

Software Review 284

Software Review SMB Enterprise Software 284

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

SEPTEMBER 7, 2024

There are multiple vendors in different segments, including Mindbody which IPO’d a SaaS generation ago and then taken private in a $2B Vista acquisition. 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. That’s the trifecta.

SaaS Payments 312

SaaS Payments Payments Payment Methods SMB 312

Tom Tunguz

AUGUST 2, 2016

Channel distribution represents one of the biggest and most important changes in customers acquisition for SMB SaaS startups in quite a while. As many of these channel partners move to newer distribution models, the brokerage channel model in particular, they represent an efficient and leveraged customer acquisition channel.

Outsourcing Services 111

Outsourcing Services SMB Acquisition Scale 111

SaaStr

DECEMBER 27, 2023

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. GGV Capital: Scaling The Top SMB SaaS Companies A deep dive on SMB metrics, a really good one. #10. Harness.io How do you handle and close so many?

Scale 284

Scale SMB Generative AI AI 284

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. of the 33 million SMBs in the US, suggesting significant room for growth. 5 Non-Obvious Learnings from Bill.com’s Journey to $1.4B

SMB 130

SMB Payments Payment Services SaaS Payments 130

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. Diversifying into the restaurant space makes sense — it’s one of the largest segments for SMB commerce.

Scale 291

Scale SMB Churn Pricing 291

SaaStr

SEPTEMBER 22, 2022

Chestnut began by discussing the ins and outs of the acquisition by Intuit. But when none of them offered a good deal, Mailchimp walked away, convinced they wouldn’t entertain any more talks on acquisition. Up until the acquisition, the company was 100% founder-owned and operated. The Deal With Intuit.

SMB 256

SMB Entertainment Acquisition Branding 256

SaaStr

JULY 20, 2022

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. ” But it’s also a reminder how hard it is to combine services, hardware and software and make money from SMBs. #3. A fairly standard SMB price point.

SaaS Payments 284

SaaS Payments Scale Payment Methods SMB 284

SaaStr

AUGUST 28, 2024

And with that, it seemed a good time to dig in with one of the great SMB leaders Bill. With a super impressive 111% NRR from SMBs. Divvy Acquisition Very, Very Successful Ramp and Brex create the most noise in the expense management space, but Bill scooped up Divvy for $2.5 Grab the final tickets here!! But Bill hasn’t.

Payments 292

Payments Payment Solutions SMB Acquisition 292

SaaStr

MARCH 23, 2021

The average SMB SaaS company has $295k in revenue per employee, and $450k in the enterprise. Private Equity did 48+ $100m acquisitions in 2020. An argument the top SaaS companies figure out how to grow their TAM … almost forever. An important metric we don’t look at often enough. We’ve seeing it live.

Investment 316

Investment SMB Acquisition Cloud 316

SaaStr

APRIL 24, 2022

BowtiedCocoon: Top SaaS SMB AEs have $125k OTEs. The Private Equity Math of 1+1=3 in SaaS Acquisitions. Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: 1. But The Best Ones Make $261k. Every Investor is Different. But Here Are 22 Reasons I Generally Say “No” 3.

Sales Hiring 293

Sales Hiring Revenue Scale SMB 293

SaaStr

DECEMBER 2, 2020

” as it now joins Salesforce in a 27B+ mega-acquisition. But Slack’s SMBs seem to have accelerated, too, since then. Slack’s remained 50/50 enterprise / SMB for 3 quarters, and close to it for 5. All 3 are holding relatively consistent enterprise/SMB ratios: 40% of revenue from outside U.S.

SMB 297

SMB Enterprise Cloud Retention 297

SaaStr

SEPTEMBER 17, 2023

The Next Best in About 5 Years. 5 Interesting Learnings from Samsara At Almost $1 Billion in ARR Top Podcasts This Week: 1.

Scale 289

Scale SMB Management Acquisition 289