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 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 192

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 192

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 140

Strategy Payment Solutions Payment Methods SMB 140

Tom Tunguz

FEBRUARY 26, 2025

Consider whether your startup is differentiating on pricing to compete with an incumbent, or if you’re selling a superior product at a premium, in which case using the same pricing model with higher fees reinforces your brand positioning. What should my unit of pricing be? The goal of UBP is to align the cost of software with the value.

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

SaaStr

AUGUST 24, 2022

SMB sales (most of Toast) is very tough to do without a highly efficient and effective sales force. Many SMB leaders have to get very, very good at outbound because of the limited deal sizes. As the brand scales, they get more of a boost from inbound. #5. 20% of new customers / locations come from referrals. . #4.

SaaS Payments 326

SaaS Payments Scale SMB Payment Solutions 326

SaaStr

APRIL 13, 2021

Thank you @jasonlk for giving me the @saastr stage +4 yrs ago to share both my story & build @pagerduty 's brand … the Sunny Delight, solution to problem fit talk. It’s also an interesting contact to Zoom , Zendesk and Slack , which recently have seen enterprise and SMB growth be about equal post-Covid. #2.

SMB 329

SMB Enterprise Scaling Startup 329

SaaStr

AUGUST 31, 2024

70% of Monday’s SMB customers are outside of tech. CrowdStrike, despite a brand-threatening outage this quarter, also grew 34% at $3.8 With that, let’s take a look at some of the latest numbers: The Thriving — this week and last: Monday.com crossed $1 Billion in ARR, growing a stunning 34% (!). Billion in ARR.

Azure 326

Azure SMB Cloud AI 326

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 21, 2023

Dear SaaStr: What is the average percentage of annual vs. monthly plan sold for a BtoB SaaS startup targeting the SMB market? Once the customers get large enough, and you have a brand … in the enterprise, for six figure deals … almost all will want to pay annually via invoice. 20%+- will pay annually to save money.

Data 282

Data SMB Payment Features Churn 282

SaaStr

SEPTEMBER 22, 2022

The Brand, the Breaking Point, and the Bootstrapping. Mailchimp has always garnered attention and interest with its off-the-wall, standout branding strategy. As successful as Mailchimp was and continues to be with the SMB target, they realized they needed to adjust their strategy for their customers as their business grew.

SMB 256

SMB Entertainment Acquisition Branding 256

SaaStr

DECEMBER 28, 2022

Roughly, once you (x) have an established brand, and (y) have a marketing engine that is working, and (z) most importantly, once demand gen has finally become somewhat routine … you’ll need a CMO. Maybe a VP of Marketing. But the last thing you probably need is a fancy title running around, spouting marketing-ism.

Scale 69

Scale Sales Hiring Growth Hacking SMB 69

SaaStr

JANUARY 24, 2021

. “Lessons from Gorgias: How to Close your First 1000 Customers Based Solely on Data” Gorgias is now the fastest-growing contact center solution, with 5,000+ SMB customers. Take a look back at how they got their first 1,000 SMB customers here. #8.

Scale 261

Scale SMB Scaling Engineering 261

SaaStr

JANUARY 3, 2021

OK, so if an SMB rep needs to make say $80-$100k in OTE (base + bonus) … and you need to clear say $300k in revenue from that rep to make the math work on your side … at say 100 closed deals a year, to bring in $300k to the company, each deal has to have a $3,000 ACV on average. You don’t quite have Asana’s brand yet.

SMB 337

SMB Pricing Sales Metrics 337

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 300

Sales Hiring Scale SMB compliance 300

SaaStr

MAY 1, 2021

At least, once you have enough of a mini-brand to be trusted. Zoom monthly billing exploded to 50% of ARR as SMB use grew 5x during Covid! At least, once you have a brand and they know they can trust you on Day 0. Once you have a brand that customers trust, more will prepay annually. More on that here. Get the deal done.

Payment Features 293

Payment Features Scale SMB Churn 293

SaaStr

NOVEMBER 22, 2020

SMB to Enterprise, decide which you want to start with and toward which you want to move. Brand includes your company values, Heritage/story, packaging, convenience, customer support, quality, segment focus, and positioning, all of which can differentiate your company from others with similar products. Geographic regions.

Scale 322

Scale Scaling Technical Review Systems Review 322

Tom Tunguz

SEPTEMBER 17, 2012

SMB SaaS companies cannot afford to pay for distribution. The most successful SMB SaaS companies (Zendesk, Expensify, Square) build communities to drive distribution. The most successful SMB SaaS companies (Zendesk, Expensify, Square) build communities to drive distribution. Those communities reinforce and build a brand.

SMB 100

SMB SaaS Branding Payment Features 100

SaaStr

JULY 22, 2022

The last few years have certainly tested marketers, but 2022 serves up a brand new array of challenges. In the eye-opening session, these marketing leaders discuss the market pulse, impactful branding, and strategies for the future. Economic Climate, Customer Behavior, & Market Trends. How do I engage my customers?

B2C 283

B2C Scale Marketing Sales Hiring 283

SaaStr

FEBRUARY 13, 2021

SMB growth in Cloud and SaaS is still going strong! There’s no seeming ceiling to the number of SMBs than can now buy SaaS and Cloud products. A bit of a challenge to the notion of the power of brand at scale. Million More Customers in 2020. Freemium is back! in marketing/ads in 2020. They did acquire 1.4

SMB 318

SMB Cloud Scaling Investment 318

Nimble - Sales

MAY 27, 2025

For small businesses, the road to growth should be straightforward: build relationships, build a brand, generate traffic, nurture leads, close deals, take care of customers, and expand your customer base.

SMB 49

SMB Branding Business 49

SaaStr

DECEMBER 8, 2022

If at almost $2B in ARR, and a market-dominating brand, HubSpot has to still do RFPs … even when selling to medium-sized businesses … well get used to it. The average SMB now uses almost 300 (!) Secrets to SMB at Scale with HubSpot and SaaStr's CEOs [link]. Even HubSpot is seeing the same.

Scale 292

Scale SMB Scaling Customer Success 292

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 103

SMB Scale Enterprise Sales 103

Tom Tunguz

OCTOBER 9, 2016

What are the attributes of the ideal SMB SaaS company, an entrepreneur asked me recently. I believe that the next wave of SaaS companies will be centered around workflows, Event Driven SaaS , and this extends to SMB SaaS. Building a brand that is synonymous with a category is a huge strategic advantage. Sales & Marketing.

SMB 100

SMB SaaS Acquisition Education 100

SaaStr

MARCH 22, 2021

Their SMB customers quintupled, right? And so what happened was, even though they added a thousand customers paying $100,000 or more a year, actually the revenue count skewed more SMB, because they grew even faster. And I don’t know why for sure, Zoom group more than the others, but it’s a reminder that brands matter.

Scale 262

Scale SMB Enterprise Branding 262

SaaStr

DECEMBER 7, 2022

Sustainability In Marketing – Leveraging Compounding Channels For Long-Term Growth with Dave Gerhardt, Founder at Exit Five, Betsy Koliba, Head of Services at Demandwell and Bridget Poetker, Director of Content & Brand at Postal. Secrets to SMB at Scale with Hubspot CEO Yamini Rangan and Jason Lemkin, Founder & CEO at SaaStr.

Scale 48

Scale VP of Engineering Scaling SMB 48

SaaStr

DECEMBER 14, 2020

Churn is a good term for your SMB and freemium customers. This is why, once you have a brand and some momentum, a lot of them will even agree to pay 3 years upfront for a discount and price protection. And sometimes they’ll churn even just for a modestly better deal. Like Verizon. The customers want to stay at least that long.

Churn 362

Churn Sales Hiring Systems Review B2C 362

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

JANUARY 16, 2023

Mike Wiacek, CEO at Stairwell, Mo Jebrini, CTO at Mashvisor, and Michael Ermolenko, CTO at Inworld.ai, discuss with Helene Ambiana, Global SMB and Startups Marketing Director at Google Cloud, how they overcame the hurdles of scaling and reached their goals. . Build an irreplaceable team . Teams are the foundation of all successful projects.

Scale 259

Scale CTO Hire Cloud Scaling 259

SaaStr

MARCH 2, 2022

Now, Zoom’s SMB count likely will grow again materially in the future as the New New World gets settled, but not for a while. Zoom is predicting 20%+ growth for enterprise, but flat revenue for “online” or SMBs. It’s just a reminder that SMBs are great. They are your brand ambassadors.

SMB 244

SMB Enterprise Churn Branding 244

SaaStr

DECEMBER 29, 2019

Enterprise deals are nothing like SMB deals, most especially over the long term. SAP, Oracle, Concur, Ariba, Successfactors … you can take some shots at these oldie products, but these brands endure for decades. We all know this, but over time the difference becomes even more stark. At least for Decades. Even post-acquisition.

Scale 353

Scale Churn Construction SMB 353

SaaStr

FEBRUARY 16, 2021

This does nothing for your brand. Almost always, SMBs suffer. So at least send the SMB leads to a rep just working those ones. It’s the lack of a toolkit to compete with 2–3 other peer vendors of the same size and brand equity. No one likes to be broken up with, folks. That Maybe They Shouldn’t Be. A lot more.

Scale 275

Scale Sales Hiring Sales SaaS 275

SaaStr

AUGUST 16, 2023

Only 20% of New Customers Come From Word-of-Mouth While 20% is still great, materially lowering their CAC, I would have expected even higher, given the strength of the brand. your customers from word-of-mouth is traditionally the way to get the tougher unit economics of SMB software to work. Getting a lot of.

SMB 245

SMB Scaling Onboarding Software 245

FastSpring

DECEMBER 7, 2023

As the Director of Corporate Development & Strategic Partnerships at WP Engine , Carl has worked on many acquisitions and partnerships, including brands like Flywheel, Perfect Dashboard, Block Lab, and recently, Delicious Brains. Can you describe the process for buying and selling a business from a brand? Jump to highlights.

Software Review 148

Software Review Technical Review Development Team Review Branding 148

SaaStr

JUNE 23, 2021

I’m basically an SMB these days. Take the time to make sure your top brand ambassadors — your sales team — are doing that job first. I lose patience here and move to a vendor I can just deploy without being forced to talk to an SDR that just wants to force me to get on the phone and screen me but doesn’t get me going now.

Scale 268

Scale Sales Hiring Sales SMB 268

Stax

MARCH 17, 2025

As one of the most familiar and trusted payment brands, PayPal gives customers confidence, reducing friction and increasing sales and AOV. Nielsen Behavioral Panel of USA with 29K SMB monthly average desktop purchase transactions, from 13K consumers between April 2022-March 2023. Webinar registration 1.

Merchant Services 88

Merchant Services Stax PayPal SaaS Payments 88

SaaStr

OCTOBER 3, 2023

Finding product market fit Moving from SMB to Enterprise or vice versa Achieving Enterprise repeatability Strategic expansion Borland has experienced all four stages at three different companies and knows what teams and functions look like for each stage of growth.

Enterprise 291

Enterprise B2B Scale SMB 291

SaaStr

FEBRUARY 14, 2024

Not for the brand or awareness, but right now. 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 was this mentality of “What can I do for marketing spend?”

Customer Success 299

Customer Success Sales Hiring Scale Headcount 299