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

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 162

AI Search AI New CTO Scale 162

SaaStr

NOVEMBER 21, 2020

Let’s look at some of the top public SaaS companies: Shopify — very SMB: 100%. Hubspot — mostly SMB: 100%. Surverymonkey — fairly SMB, but going more enterprise: 100%. Zendesk — 116%, mix of SMB and enterprise. Developer-focused, but still fairly SMB. And mostly SMBs. 119% net revenue retention.

Retention 349

Retention SMB SaaS Enterprise 349

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? 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

Tom Tunguz

FEBRUARY 26, 2025

Price low to minimize adoption friction, grow quickly, and then move up-market after developing broad adoption. Skimming is less common in the software world because few startups develop a product at launch that will be accepted by the most sophisticated customers (and those willing to pay prices that generate the greatest margin).

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

SaaStr

SEPTEMBER 9, 2021

Bill.com has become an SMB powerhouse, with 120,000+ customers and a stunning $25B+ market cap. Bill.com had to develop a network that today has millions on vendors processing bills and payments on it. But the accountant channel is high volume, SMB play. There are 6m SMBs that buy SaaS software. Go find them.

SaaS Payments 63

SaaS Payments Payments Payment Services 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

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. But it embraced bigger and bigger deals , including its first seven figure deals, while maintaining its long tail of developers.

SMB 329

SMB Enterprise Government compliance 329

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

SaaStr

AUGUST 27, 2022

Salesforce: “We’re finally seeing slowdown now in our commerce, media, telecom, and SMB segments”. And at the other end of the spectrum, folks at the intersection of commerce and SMB like Shopify have taken the biggest hit to post-Covid growth. But e-commerce, media / comms, and SMB are under pressure. We sort of knew that.

SMB 292

SMB Scale Cloud Trends 292

SaaStr

MARCH 9, 2022

Focusing on smaller developers, in some ways it’s been a bit overshadowed by AWS, Azure, and Google Cloud. DigitalOcean is growing an impressive 37% at $500,000,000 in ARR, and staying very SMB with 600,000+ customers, but still driving deal sizes up a bit. From so-so NRR (101% in 2020) to Top-Tier for SMBs (116%) in 2 years.

Azure 272

Azure AWS SMB Cloud 272

SaaStr

AUGUST 8, 2019

The first step in success with SMB clients is to recognize that it’s not a one size fits all scenario. Companies need a specialized approach for SMB accounts, different than the tactics used for Enterprise. Agnes Bazin | Chief Development Officer @ Doctolib. The topic of the day is secret to SMB sales. Andrei B.:

Sales Recruiting 125

Sales Recruiting SMB Scale Sales Hiring 125

SaaStr

APRIL 28, 2025

This will be particularly transformative for SMB-focused businesses doing high-volume, transactional deals. Companies will need to develop clearer pricing tiers, transparent discount structures, and simplified proposals. It can handle pricing questions, objections, and proposals without emotional baggage or commission pressure.

AI 244

AI Underperforming Technical Team Sales Technical Review 244

SaaStr

JANUARY 23, 2021

We’ve seen a lot of leaders with tons of SMB customers and a smaller number of $100k+ deals, but Cloudflare is perhaps the most extreme here. Like many similar developer-centric products, the vast majority of customers come in via self-serve, but as the deals grow, sales is brought in. #2. 48% of revenue outside the U.S.

Scale 313

Scale SMB Cloud Enterprise 313

SaaStr

APRIL 30, 2021

A great benchmark for developer-centric mission-critical services. 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%.

SMB 324

SMB Benchmarks Enterprise B2B 324

SaaStr

AUGUST 8, 2019

The first step in success with SMB clients is to recognize that it’s not a one size fits all scenario. Companies need a specialized approach for SMB accounts, different than the tactics used for Enterprise. Agnes Bazin | Chief Development Officer @ Doctolib. The topic of the day is secret to SMB sales. Andrei B.:

Sales Recruiting 111

Sales Recruiting SMB Scale Sales Hiring 111

SaaStr

SEPTEMBER 29, 2022

So lots of folks talk about GitLab as a leading in software development and devops, but GitLab also has sort of a quieter cousin that also IPO’d: JFrog. JFrog started off as the #1 binary repository and has expanded from there as a multi-product suite for software development. 100k+ customers are the engine now.

Scale 292

Scale SMB Software Development Cloud 292

SaaStr

JANUARY 24, 2021

“How To Collaborate, Manage & Work With Developers With Jeff Lawson, CEO Twilio” Our deep-dive with Jeff Lawson on how to really manage a great dev team has been very popular, both on YouTube but also on our podcast: #2. Take a look back at how they got their first 1,000 SMB customers here. #8.

Scale 261

Scale SMB Scaling Engineering 261

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. One of the most interesting examples is Microsoft’s Office 365 SMB business. It’s the most successful SMB SaaS acquisition channel ever built. by Thomas Hansen.

Outsourcing Services 114

Outsourcing Services SMB Acquisition Scale 114

SaaStr

APRIL 24, 2022

BowtiedCocoon: Top SaaS SMB AEs have $125k OTEs. SaaStr 545: Marketing to Developers: Why Happy is Our Hack with DigitalOcean CMO Carly Brantz and SaaStr GM & SVP, Marketing Amelia Ibarra. Each week, we round up our most popular content so you can catch up on anything you may have missed. But The Best Ones Make $261k.

Sales Hiring 293

Sales Hiring Revenue Scale SMB 293

SaaStr

JANUARY 23, 2021

We’ve seen a lot of leaders with tons of SMB customers and a smaller number of $100k+ deals, but Cloudflare is perhaps the most extreme here. Like many similar developer-centric products, the vast majority of customers come in via self-serve, but as the deals grow, sales is brought in. #2. 48% of revenue outside the U.S.

SMB 274

SMB Cloud Enterprise Scale 274

SaaStr

JUNE 22, 2023

This can save you 6–9 months of product development time in the early days. SMB folks want to go upmarket because there is too much churn in SMB. More here: A Simple Commitment Test For You And Your Co-Founders – SaaStr Not doing enough potential customer interviews. Go talk to 20–30 first. B2B folks want to do B2C.

SMB 274

SMB SaaS B2C Interviewing 274

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). 135% NRR from larger customers and 120% for $5k+ customers remains top-tier, especially for a vendor with plenty of small SMB customers. You can just learn so much.

SMB 305

SMB Outsourced Development Enterprise Scale 305

SaaStr

NOVEMBER 16, 2021

The top sessions so far (click on them to register) are: #1 “How to Increase Revenue and Grow Your Customer Base by 10X Through the Power of Self-Serve and Direct Sales with Asana’s COO and Figma’s CCO” #2 “Product-led Growth: How to Execute Across the Full Funnel with Reprise’s VP of Marketing and VP of Sales” (..)

Scale 261

Scale Scaling SMB Revenue 261

Sales Hacker

JANUARY 9, 2023

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. SMB, mid-market, and enterprise: What’s the difference? SMB: Small and Medium-Sized Businesses. Benefits of selling to SMB.

SMB 104

SMB Scale Enterprise Sales 104

SaaStr

JUNE 3, 2023

So it’s really probably easier if you start in freemium, SMB, consumer, or developer tools. But they started as a consumer/SMB play, it wasn’t enterprise yet, and they’d been building and working on software for years. Dylan Field was already known as the top intern ever at Flipboard when he worked there.

Software Review 240

Software Review SMB Enterprise B2B 240

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. Everything is aggressively A/B tested, including new product development. So it’s doing what Wall Street wants today. But is Duolingo SaaS? Well, it’s SaaS-ish. 5 Interesting Learnings: #1.

Scale 318

Scale B2C SMB B2B 318

SaaStr

APRIL 8, 2020

Hiver’s Free Shared Inboxes for SMB. UruIT is a top software development agency that offers services such as product discovery, web & mobile app development, product management, Machine Learning consulting, and UX design. Where can I find the deal? What are they all about? during the COVID-19 pandemic.

Artificial Intelligence 304

Artificial Intelligence Machine Learning SaaS Consulting 304

Tom Tunguz

SEPTEMBER 13, 2016

When an SMB SaaS startup is young with quickly growing revenues, more of the same works. For some SMB SaaS companies, generating this kind of lead volume even at scale isn’t a challenge. There is no universal answer to which direction to pursue: remain in the SMB segment and cross-sell or move up-market, or both.

SMB 100

SMB Scale Startup Marketing 100

SaaStr

APRIL 11, 2021

2 “The Secret Sauce to Scaling to $1B: How to Achieve SMB and Mid-Market Success with Zendesk” A great session from two top VPs at Zendesk on how to sell and scale to SMBs and mid-market alike. #3. 4 “SOC 2 Demystified: The Key to Closing Enterprise Deals with Vanta CEO Christina Cacioppo.”

Scale 274

Scale SMB Scaling Retention 274

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. Develop a demand strategy and be patient. Abandon your core at your peril.

Sales Hiring 300

Sales Hiring Scale SMB compliance 300

SaaStr

OCTOBER 30, 2021

Their CEO will join us at SaaSr Scale 2021 on December 15 to talk about using data to get to 10,000 SMB customers! I asked Aasif Osmany to share his learnings as a top-performing SMB VP of Sales, below. My personal objective was simple, learn as much about SMB SaaS as I could and move on to another company to continue learning.

Scale 284

Scale Sales Hiring Sales Underperforming Technical Team 284

SaaStr

OCTOBER 26, 2023

In a year like this, SMB is doing worse, with a lot more churn and startups going out of business. But in other years, SMBs are jumping in the boat, so you get amazing growth long-term with a multi-segment strategy. But in other years, SMBs are jumping in the boat, so you get amazing growth long-term with a multi-segment strategy.

Sales Hiring 281

Sales Hiring AI SMB Scale 281

Tom Tunguz

APRIL 8, 2015

There’s a familiar path now to SaaS companies that start in the SMB (small-to-medium business) part of the market. In short, new startups leverage a distribution advantage to acquire SMB customers at scale. SMB 3-7% 31%-58%. SMB customers tend to go out of business more frequently than bigger businesses.

Innovation 209

Innovation Startup Scale SMB 209

SaaStr

NOVEMBER 16, 2021

Positions Needed: Developers (Front-End and Back-End), Client Applications, Core Services/Platform, Analytics, and DevOps. Positions Needed: Enterprise AEs, Mid-Market & SMB AEs, SDRs, Sales Ops, Sales Engineer. Positions Needed: Enterprise CSM, Mid-Market & SMB CSM, Customer Support Reps, Implementation/Solutions Engineer.

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

DECEMBER 17, 2020

. #2: “Stop Losing Customers: 5 Steps to Creating Customers for Life with Freshworks” A very popular deep-dive on SMB customer success with $100m+ ARR Freshworks. #3: 4: “The Art of SaaS Negotiations: 3 Steps to Develop an Objection Handling Framework with Pandadoc.” Just do it! #4:

Scale 252

Scale Scaling SMB Acquisition 252

SaaStr

APRIL 7, 2021

“SaaStr 419: How To Collaborate, Manage & Work with Developers with Jeff Lawson, CEO of Twilio and Jason Lemkin” Jeff has been speaking >a lot< on this topic with his book, so we took a much deeper dive than others on this and related topics. And how to win in a very competitive market. #7.

Scale 239

Scale SMB Churn Scaling 239