SaaStr

MAY 4, 2025

Dear SaaStr: How will Ai Change Sales in The Next 12 Months? 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. Were talking about 2545% of routine deals being closed by AI alone.

AI 162

AI Scale Sales SMB 162

SaaStr

FEBRUARY 8, 2025

Forget everything you know about SMB customer success. Leaders are exploring: AI-augmented CS motions Digital-first success programs at scale Predictive success modeling New monetization models for CS services The bottom line?

Customer Success 273

Customer Success Scale Government Systems Review 273

SaaStr

FEBRUARY 13, 2025

but also In high-growth AI-fueled spaces, massive competition as well. How many AI-first tools are Freemium? Not just for consumer and SMB. But what about the “cost of AI” many start-ups ask? And first, costs are falling so quickly in AI this year, it’s epic. Get better at using AI.

AI 201

AI ChatGPT SMB Enterprise 201

SaaStr

APRIL 26, 2025

Before taking the helm at Carta 6 years ago, Jeff spent 15 years at Oracle leading both Enterprise and SMB software/hardware divisions. The Truth About SDRs and AI in 2025 No, AI isn’t replacing your SDR team. He also put in 4 years at Doximity building their S&B organization from scratch.

Scale 173

Scale Sales Hiring AI SMB 173

SaaStr

APRIL 2, 2025

The support space has been turned upside down by AI, with as much as 40% of all support issues now handled by AI at many leaders. 50% Attach Rates for AI In $30k+ Deals, But Much Lower for SMBs This is also what I’ve seen in the contact center. It’s one of the fastest-changing spaces in B2B.

Scale 271

Scale AI SMB B2B 271

SaaStr

APRIL 29, 2025

The ultimate gathering of SaaS and AI leadership is about to happen in San Francisco. SaaStr Annual + SaaStr AI Summit 2025! We’re bringing together the true founders, revenue leaders and product visionaries that are actually driving the next wave of AI first software. It’s days away now! Not talking heads.

AI Search 159

AI Search AI New CTO Scale 159

SaaStr

APRIL 28, 2025

And come see so many more great convos like this at 2025 SaaStr Annual + AI Summit on May 13-15 in SF Bay , including the CEOs and CXOs at vertical SaaS leaders ServiceTitan, Clio, MangoMint, Owner and so many more! This creates an ideal environment to perfect both your product and go-to-market motion before moving upmarket.

Scale 263

Scale Transportation Scaling SMB 263

SaaStr

APRIL 14, 2025

It’s 50% about the intersection of AI + B2B, 50% about GTM in 2025+, and … 50% about helping you meet the best of the best! With a New, AI Demo Stage from 100+ Top AI Start-Ups! AI is transforming SaaS, and were dedicating two massive stages to the SaaStr.AI The SaaStr.AI Summit Is Back and Bigger.

VP of Engineering 195

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 195

SaaStr

AUGUST 24, 2024

So I think AI will destroy Outbound. First, even the AI we have today used correctly is a huge aid to AEs and SDRs alike. And that’s where I think Outbound will be partially destroyed by AI. Every single week: “I’ve got a proprietary AI system and I’ll do targeted outbound with it. What do I mean?

AI 312

AI SMB Enterprise Startup 312

SaaStr

JANUARY 3, 2025

If you missed part 1 of this interview, you can catch up on their conversation about the current state of SaaS, evolving board meeting formats, and how AI is reshaping the industry. In sales, t he more SMB you are, the more you should lean on your bench. Lean into self-motivated talent.

Sales Hiring 290

Sales Hiring Scale Systems Review Interviewing 290

Tom Tunguz

FEBRUARY 26, 2025

There are a few alternatives for AI-driven products: Triple the per seat price : If the AI agent is 3x as productive as a human, the software company could charge 3x as much per seat. Move to usage-based pricing : AI software might be priced like databases, charging for compute. across major SaaS vendors.

SaaS Payments 283

SaaS Payments Pricing Strategy Scale 283

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. With AI, this gets even easier. The post How to Build Go-to-Market Efficiency in SMB Sales with Owner.com CRO Kyle Norton appeared first on SaaStr.

Scale 306

Scale SMB Sales Hiring Sales 306

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. Yeah, I think especially now with AI, there so many garbage messages and people are so tired of being solicited to and sold to and advertised to all the time.

SMB 108

SMB Sales Recruiting Branding Sales Hiring 108

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 286

Sales Hiring AI SMB Scale 286

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 147

Payments Payment Services SaaS Payments Payment Solutions 147

SaaStr

NOVEMBER 27, 2024

But it’s not, and it’s being reinvented, so what’s changed in the space with the introduction of automation and AI? 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?

SaaS Payments 260

SaaS Payments Payments Payment Solutions Payment Services 260

SaaStr

MARCH 8, 2024

With everything in AI moving so rapidly, what’s the best way to price Artificial Intelligence products or SaaS tools with custom AI features and integrations? So we asked the expert, Sandhya Hegde, General Partner at Unusual Ventures to share her best practices and trends for pricing and packaging AI products. Usage is volatile.

AI 273

AI Artificial Intelligence Pricing SaaS 273

SaaStr

APRIL 24, 2025

Whatfix is holding an “AI in Customer Success: Reality Check” meet-up in San Jose from 1-5pm with an afterparty at M8trix Casino Sprinto is hosting Brews & Big Ideas from 4-7pm at the epic Fieldworks outdoor brewery just down the street from the venue. Past speakers, sponsors, partners and more, look for an invite.

AWS 173

AWS SMB AI Innovation 173

SaaStr

SEPTEMBER 7, 2024

Automation and AI are critical in SMB Vertical SaaS … due to a lack of labor Automation and AI are less about efficiency in SMB vertical SaaS than simply dealing with a lack of labor. Automation and AI solve this. #3. Onboarding has to be much slicker for SMBs. Today, the customers expect it all. #2.

SaaS Payments 317

SaaS Payments Payments Payment Methods SMB 317

SaaStr

AUGUST 16, 2024

Andrew Bialecki, CEO Klaviyo This will be an epic deep dive on just how you get an SMB+ app to almost $1B in ARR — all while having incredibly happy customers. And a deep, honest and data-driven look at what works, and what doesn’t today, in AI. This will be a special one. And an epic one. #2. Across 16,000+ customers.

CTO 312

CTO SMB AI B2B 312

SaaStr

AUGUST 31, 2024

There are so many mixed signals: Unicorn product is up 2x over last year, but layoffs continue AI spend is fast and furious, with Google Cloud, Microsoft Azure, etc. Overall, SaaS leaders tied to non-tech buyers or tied to AI are still growing at epic rates. 70% of Monday’s SMB customers are outside of tech. Billion in ARR.

Azure 328

Azure SMB Cloud AI 328

SaaStr

DECEMBER 27, 2023

For B2B Generative AI Apps, is Less More? with Andreessen Horowitz This one on AI was super popular! #5. 10 Learnings on High Velocity Sales to SMB with Gorgias’ CEO and VPS Gorgias has 13,000 SMB customers. 10 Learnings on High Velocity Sales to SMB with Gorgias’ CEO and VPS Gorgias has 13,000 SMB customers.

Scale 289

Scale SMB Generative AI AI 289

SaaStr

SEPTEMBER 15, 2023

They released many more products, with Freddy AI in 2018 and, as of last month, launched the Freshworks Customer Service Suite, which is an omni-channel for B2C to engage with customers on Instagram and other places. The average SMB customer would buy 4-5 seats of Freshdesk. Inbound isn’t just about SMB customers. The lesson?

Sales Hiring 289

Sales Hiring Scale SMB SaaS 289

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. They expect products to be more elegant and integrated, with features like payments, workflow, and AI.”

SMB 130

SMB Payments Payment Services SaaS Payments 130

SaaStr

AUGUST 30, 2023

G2 CEO Godard Abel deep dives into his original vision for G2, going multi-product, selling with multiple sales teams, demand gen spend, and why AI is the most important thing right now. You can filter your search by industry, whether you’re SMB, mid-market, or Enterprise, etc. AI is just a better interface than forms-based searching.

AI Search 245

AI Search AI ChatGPT Scale 245

SaaStr

MAY 24, 2024

ARR: SMB leader HubSpot Enterprise vertical SaaS leader Veeva And collaboration leader DropBox All at the same ARR, but with very different growth profiles, and profitabilty. So the #2 topic in SaaS today is probably profitability and efficiency. #1 But profitability is a close second. And the message to founders is confusing.

SMB 312

SMB SaaS AI Scaling 312

SaaStr

OCTOBER 29, 2023

10+ Actionable Things You Can Do To Scale Faster In The Early Days The Chat GPT Growth Story: How AI is Changing the Way We Work The Challenge with SMB SaaS: High Growth Can Only Mask High Churn For Just So Long (Updated) Dear SaaStr: My Top Sales Rep Made $600,000 a Year — And Just Quit! What Happened? What Happened?

ChatGPT 278

ChatGPT Scale SMB Sales 278

SaaStr

FEBRUARY 14, 2024

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. And that’s where AI comes in. 43% of CS teams have adopted AI, which means that 57% have not.

Customer Success 304

Customer Success Sales Hiring Scale Headcount 304

SaaStr

JANUARY 3, 2024

Shrav added that if you want to close bigger deals, not just Enterprise, but mid-market and SMB as well, that the moment you’re ready to Go-To-Market, you need to become compliant. Shrav sees security and AI as the two biggest faces in software for the next decade. “Gartner’s newest I.T. .”

AI 162

AI SMB Sales Hiring compliance 162

SaaStr

OCTOBER 25, 2023

Leveling Up PLG to Accelerate SMB Customers, Including More Attention to Onboarding I love seeing this, it can seem hard to invest heavily in small customers, but if you don’t especially invest in onboarding, that’s a big shame. A big change from their roots with smaller SMBs. #4. Automation / AI is Already a Big Deal.

SMB 299

SMB AI Onboarding Cloud 299

SaaStr

SEPTEMBER 17, 2023

SaaStr 684: A Deep Dive Into G2, The Power Of AI, Going Multi-Product, And The 2023 Ecosystem  4. The Next Best in About 5 Years. 5 Interesting Learnings from Samsara At Almost $1 Billion in ARR Top Podcasts This Week: 1. SaaStr 685: Why Investors Love SaaS with SaaStr CEO Jason Lemkin and QED Partner Amias Gerety on Fintech Beat     3.

Scale 295

Scale SMB Management Acquisition 295

SaaStr

MARCH 28, 2025

Make sure your product is API-friendly and AI-friendly and designed to work well with others. More here: 7 Thoughts on Building Your First Partner Program And how Gorgias got to 10,000+ SMB customers with partners here: Decide which of these is most critical to your business and focus there first.

Scale 141

Scale Sales Hiring SMB Enterprise 141

SaaStr

APRIL 9, 2023

SaaStr 647: Scaling The Top SMB SaaS Companies: What It Takes with GGV Capital Managing Director Jeff Richards and GGV Capital Partner Tiffany Luck   3. LIVE Workshop Wednesday with Theory Ventures: The Impact of Generative AI on Software 4. All Your VPs Really Need to Do is Tilt the Curve Top Podcasts This Week: 1.

Scale 246

Scale SMB Generative AI Management 246

Sales Hacker

JANUARY 7, 2025

So you need to have that because those, especially if you think about SMB, They don’t have, I would say, technical people inside their organization. You know, we’ve got AI, STRs and AI now like cold calling and things. I think I’m a big fan of AI. Sometimes it’s the IT shop at the corner.

Outsourcing Services 114

Outsourcing Services Scale Outsourced Development AWS 114

SaaStr

OCTOBER 20, 2022

Note this doesn’t include SMB spend, it’s enterprise focused): In a slightly more dated survey, Gartner found in July 69% of CFOs plan to increase their digital spending in 2023. 32% are increasing investment in artificial intelligence (AI) and 24% in hyperautomation”, per Gartner. That’s not 100%.

Forecasting 305

Forecasting Artificial Intelligence Software Business 305

SaaStr

MARCH 22, 2024

After switching to SaaS, she started as an SMB sales leader with no prior management or SMB sales experience. Automation and AI could solve for that. Different Pathways to CRO For Jane Kim, former CRO of CircleCl,, she used to work in finance before transitioning to SaaS.

Scale 305

Scale Underperforming Technical Team SMB Finance 305

Payrix

JANUARY 28, 2025

AIs role in payments Artificial intelligence is reshaping the payments landscape. Companies are leveraging AI to enhance customer experiences, streamline operations, and combat fraud. Matt stressed that businesses not incorporating AI into their strategies risk falling behind. AI certainly made the list this year.

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Payments Payment Solutions Merchant Services Payment Methods 130