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 157

AI Scale Sales SMB 157

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 260

Scale Transportation Scaling SMB 260

SaaStr

JULY 11, 2025

Some can stay SMB only to $100m ARR, even $1B ARR. The pace here has accelerated even more with AI. But not most of us. It’s often the only way to scale meaningfully in SaaS. Competition and Differentiation: Founders worry about competitors copying their product or undercutting them on price. And you should.

Scale 234

Scale Part-Time VPE Scaling Sales Hiring 234

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 284

Sales Hiring Scale Systems Review Interviewing 284

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 279

SaaS Payments Pricing Strategy Scale 279

SaaStr

NOVEMBER 27, 2024

It’s dropped “Video” from its name as it has gone communications and AI-first: $4.7B It’s dropped “Video” from its name as it has gone communications and AI-first: $4.7B So Zoom has entered its mature stage, but it’s also now rebooting itself. And it still trades at 5x ARR. #1.

SMB 274

SMB Churn Enterprise Acquisition 274

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 203

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

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 270

Scale AI SMB B2B 270

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

JULY 23, 2025

Replit : After languishing at sub-$10M ARR for 8 years, suddenly 10x’d to $100M ARR in the exact same 8-month window following their AI Agent launch in September 2024. ” The AI handles architecture, data modeling, user experience, and deployment. This isn’t coincidence.

Software Review 193

Software Review Technical Review Development Team Review Systems Review 193

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

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 257

SaaS Payments Payments Payment Solutions Payment Services 257

SaaStr

JUNE 4, 2025

As a “prosumer” app there is overlap for SMB and freemium B2B apps. Resolve 68% of Support Issues with Automation and AI Chime achieved 68% of support interactions resolved without human intervention, directly impacting their path to profitability. In a business serving 8.6

Outsourcing Services 206

Outsourcing Services Scale Banking Customer Lifetime Value 206

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 161

AI Search AI New CTO Scale 161

Sales Hacker

DECEMBER 17, 2024

Feeling that AI FOMO? Thats why HG Insights created The Next Generation of Sales AI report to calm the FOMO and help you bring AI to your GTM teams. It includes a breakdown of the Sales AI landscape, adoption of GenAI and Sales software across buyer groups. Plus, an analysis of the top 75 trending sales AI tools.

Scale 102

Scale Engineering Acquisition Scaling 102

SaaStr

NOVEMBER 3, 2024

How Long Will the AI Bubble Last? #3. One Thing is Clear: AI Is Leading to 1000+ New Competitors in SaaS #4. State of the Cloud 2024: The Cloud AI Era with Bessemer Venture Partners #3. Approaching Half a Million Customers: How to Win in SMB | BILL CEO and Founder René Lacerte #5. Top Posts: #1. Genesys Files to IPO.

Cloud 273

Cloud AI SMB SaaS 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 206

AI ChatGPT SMB Enterprise 206

Sales Hacker

JUNE 17, 2025

Not to start off with an AI question. Dennis Lyandres: Okay, so Sophie Buonassisi: when it comes to cross vertical software and ai, [00:04:00] what are you really advising founders on today? And then, you know, I think there’s two schools of kind of AI transformations. So Sophie Buonassisi: I love it. Shall shall do it.

AI 88

AI Technical Advisors Underperforming Technical Team Sales Hiring 88

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.

Payments 130

Payments Payment Solutions Merchant Services Payment Methods 130

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 146

Scale Sales Hiring SMB Enterprise 146

How To Buy Saas

FEBRUARY 25, 2025

Rapid SMB adoption with 200K+ customers. Startups, SMBs, and mid-market; teams wanting all-in-one marketing + sales. Einstein AI adds predictive automation (lead scoring, etc.). Increasing AI assistance for content and timing. auto-generated emails, AI chatbots in service). Market share leader (21.7%

Scale 52

Scale Underperforming Technical Team Technical Review Marketplace as a Service 52

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. Importantly, ATS platforms have evolved with AI-driven features , diversity and bias reduction tools , and deep analytics to meet todays hiring challenges.

Systems Review 52

Systems Review Sales Recruiting Sales Hiring Technical Review 52

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 269

Customer Success Scale Government Systems Review 269

SaaStr

OCTOBER 16, 2024

The bar has gone up, and it’s not just in AI. Buyers are expecting much more from a product, and yes, AI is accelerating those expectations. Google Cloud , Azure, and GitLab, all tied directly or indirectly to AI, are seeing massive acceleration. So non-tech is strong, we all know AI is strong. 1: AI is Table Stakes.

Sales Hiring 317

Sales Hiring Scale AI SaaS 317

Chart Mogul

DECEMBER 12, 2024

2024 was a big year for SaaS with AI in the spotlight and new pricing models shaking things up. Oh and spoiler AI features in everything, everywhere. Kathleen Booth , SVP of Marketing and Growth at Pavilion SaaS brands will double down on brand-building as AI commoditizes traditional demand gen. What will 2025 bring?

Fractional VPE 40

Fractional VPE Software Review SaaS Part-Time VPE 40

SaaStr

MAY 5, 2025

I’m seeing an alarming trend across the SaaS landscape that’s going to separate winners from losers in the next 18 months: The AI Slow Roll. It’s the Product leader confidently declaring AI “isn’t ready for prime time because of hallucinations.” Attention Sales Reps: AI is Coming For Your Job.

AI 277

AI Fractional VPE Scale SaaS 277

SaaStr

FEBRUARY 5, 2025

Everything changed in 2023 as automation became the focus, and then again in 2024 as full AI agents were rolled out across its customer base. Their rollout of AI customer service agents across 500+ top brands offers valuable insights into the future of automated customer support. Here’s the story – and deep dive.

New CTO 167

New CTO CTO Artificial Intelligence SMB 167

Stax

APRIL 3, 2025

Keep in mind that the right solution for a startup or SMB may not necessarily be the best for large firms or high-volume enterprises. Here are some key trends shaping the future of eCommerce payments: The rise of AI-driven fraud prevention AI has evolved from just a buzzword to the driver of efficiency in most industries, including eCommerce.

Payment Methods 88

Payment Methods Merchant Services Payment Solutions Payment Services 88

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. 46:43 Pick up the phone: Human connection wins in an era of AI and automation. Discussed in this Episode: How to turn coworkers into mentorsand why it matters.

Scale 66

Scale Sales Hiring Scaling Revenue 66

SaaStr

JULY 15, 2025

The AI Replacement Reality Check: What You Can Actually Automate in Your SaaS Today The question isn’t whether AI will transform your SaaS business. Real-World Proof : SaaStr recently sent 4,495 AI-generated emails in two weeks and achieved the #1 response rate on their AI platform. It already has or will soon.

AI 236

AI Sales Hiring Scale B2B 236

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.

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Outsourcing Services Scale Outsourced Development AWS 117

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

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. Rudimentary AI to, to then be able to extend it extensibility that you can bring to other apps.

Scale 63

Scale VP of Engineering Outsourcing Services Enterprise 63

OpenView Labs

APRIL 30, 2024

Voiceflow is a platform to build mid-high complexity AI assistant. We needed to find a way to get more people launching production AI assistants on Voiceflow in a self-serve way. Its the best tool available for building a mid-high complexity AI assistant with your team, but takes a while to master and has a steep learning curve.

AI Search 52

AI Search AI Scale Enterprise 52

Sales Hacker

FEBRUARY 25, 2025

Obviously, SMB, smaller companies, there’s risk when the market’s the way it is. Katrina Wong: Think about AI and the possibilities of that, right? Like with generative AI. And of course we got to the generative AI topic. Everyone’s trying to go upmarket. It’s kind of a common theme.

Sales Hiring 84

Sales Hiring Marketing Technical Review Sales Recruiting 84

SaaStr

APRIL 1, 2025

Sam Blond and Jason Lemkin joined together for a live SaaStr Workshop Wednesday looking at what has and what hasn’t changed in 2025 in GTM in general and in the age of AI. Even in the Age of AI. Toast: Domain Expertise Isn’t Always Transferable.

Scale 207

Scale Sales Hiring Underperforming Technical Team Headcount 207

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