SaaStr

JUNE 19, 2025

✨ Lemkin (@jasonlk) June 16, 2025 The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do, If You Use The Tools Properly) I get this question at least 3x a week: “Jason, we tried AI sales tools and they just don’t work. I’ve been in B2B and Saa sales for 15+ years.

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Scale AI Sales Hiring Sales 273

SaaStr

JULY 11, 2025

B2B SaaS founders tend to share a lot of common concerns, especially as they navigate the different stages of growth. Later, it’s about building a repeatable sales process and ensuring your infrastructure can handle the growth. They hire VPs they know aren’t great, to finally get it domestically. Ok, almost all founders.

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Scale Part-Time VPE Scaling Sales Hiring 235

SaaStr

MARCH 15, 2025

It’s live on SaaStr.com itself and you can also access it here and talk to AI Jason about any of 1000s and 1000s of B2B, sales, SaaS, VC, etc. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days.

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Sales Hiring AI Scale Compensation 258

SaaStr

JUNE 29, 2025

👉 10 Things Deel Did to Get from $1M to $100M ARR in 20 Months Deel recently announced it had crossed $1 billion in ARR, joining the exclusive club of B2B companies that have reached true unicorn revenue status. Scaled Sales Without Revenue Operations (And Paid Dearly) The Explosion : From 2 AEs to 50 AEs in one year.

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Payment Services Sales Hiring Payment Solutions SaaS Payments 189

SaaStr

MARCH 23, 2025

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. Create Compelling Economic Incentives For sales talent, compensation is critical.

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Sales Recruiting Sales Hiring Scale AI 242

SaaStr

JULY 1, 2025

Insights from Jasper Carmichael-Jack, CEO of Artisan at 2025 SaaStr AI Summit About Artisan: AI-powered sales platform building the end-to-end solution —from marketing personalization to AE automation across the entire revenue cycle. The latest AI B2B to go through hyper-growth. Sales is messier.

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Scale Software Review Sales Hiring AI 219

SaaStr

APRIL 7, 2025

This has massive implications for B2B SaaS. I’m shocked we don’t already have this for sales calls. By the end of the year, every single sales call should have a digital representative that can fill in when the human doesn’t know an answer. This will utterly change how we do sales.

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AI B2B ChatGPT Scale 214

SaaStr

APRIL 15, 2025

On everything from how to hire a great VP of Sales, to reviewing investor memos, to helping (many!) Not for selling per se, but for answering sales-related questions. So we do love our SaaStr AI. It’s not perfect, but in its first month alone, it’s answered over 6,000 chats and questions from the SaaStr community!

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Sales Hiring AI Sales B2B 293

SaaStr

MAY 10, 2025

A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable: Hire Truly Product-Savvy Customer Success Managers at First Focus on hiring people who customer-focused product nerds to start. Measure time-to-value and/or time-to-go-live. Be careful here.

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Sales Hiring Customer Success Scale Retention 232

SaaStr

JULY 2, 2025

The Most Unconventional CMO Story in B2B Raaz Herzberg joined Wiz as employee #5. The Hiring Philosophy That Built a $23B Company “Every single person you hire should be your best hire ever. Unless you leave an interview very excited—like ‘I wish this person was here right now’—don’t hire them.”

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Sales Hiring Marketing AI Cybersecurity 175

SaaStr

MAY 29, 2025

At SaaStr + AI Summit 2025, Jason Lemkin and Kyle Norton CRO of $1B+ vertical SaaS leader Owner (where Jason is on the board) did a deep dive on AI in Sales today. This isn’t about being an AI expertit’s about demonstrating active engagement with AI tools and genuine interest in how they can transform sales outcomes.

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Sales Hiring Underperforming Technical Team AI Scale 239

SaaStr

MARCH 12, 2025

So at SaaStr Annual, Dave Kellogg did a great deep dive on “5 Things Every B2B CEO Needs to Know about Marketing” In the Age of AI it’s even more true today, so I wanted to update our SaaStr take-aways from the deep dive. Better to hire for your specific needs and stage.

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Sales Hiring Marketing Technical Review Underperforming Technical Team 202

SaaStr

JUNE 6, 2025

The SF Bay Area is still the epicenter of B2B and tech. Unmatched Density of B2B Talent The Bay Area has the highest concentration of SaaS founders, executives, and veterans who’ve scaled companies to $100M+ ARR, IPOs, and beyond. It’s Still the Hub for B2B and SaaS. Dear SaaStr: Should I Move My Start-Up to SF Bay Area?

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Sales Recruiting Scale Sales Hiring B2B 225

SaaStr

MAY 24, 2025

If you can maintain this pace and improve your metrics (like NRR and sales efficiency), you could still build a significant, valuable B2B business over time. Fundraising and Hiring Challenges Raising a Series A or B at 35% growth will be essentially impossible. However, youll need to be patientits a slower path.

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Sales Hiring B2B Churn Retention 204

SaaStr

JULY 11, 2025

Sales isn’t going anywhere in the Age of AI. OpenAI has a big sales team, Windsurf does, Anthropic has a great one. Especially the next generation of them: Perplexity has scaled to 5,000 enterprise customers with just 5 sales reps. Cursor built a $400M business with what appears to be a skeleton GTM team.

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Scale AI Headcount Sales Hiring 185

SaaStr

APRIL 8, 2025

Many of the early break out leaders in AI for B2B and otherwise have been “small but mighty teams” Honestly we’d all love it if that scaled. And thus — hiring more. They they are doubling down and hiring even more to keep these gains going. So that 30 person, $100m ARR AI B2B start-up?

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AI Sales Hiring Scale B2B 283

SaaStr

JUNE 20, 2025

The Great Spending Showdown: AI vs SaaS in 2025/2026 — What Every B2B Leader Needs to Know We’re witnessing the most dramatic shift in enterprise tech spending since the cloud migration began 15 years ago. billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3

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AI Search Artificial Intelligence AI CTO Hire 289

SaaStr

MAY 3, 2025

It can answers tons of questions, from how to hire a VP of Sales and where and whom to meet at SaaStr Annual. Our AI Can Review Your Outbound Email Copy, or Even Just Create it For You From Scratch Tell our AI about your B2B business: ARR, ACV, growth, ICP, etc. Really Well. Our AI is really, really good at this. Ask our AI.

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Sales Hiring AI Interviewing B2B 161

Kellblog

JUNE 1, 2025

When a B2B SaaS startup is hiring their first salesperson, I think they should look for someone who: Is a dyed-in-the-wool seller with sales blood coursing through their veins. Their first sales job was in high school and they’ve sold anything from dictionaries to shoes to cars early in their career. Go find one.

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Sales Hiring Startup Scale Onboarding 60

SaaStr

JUNE 7, 2025

Companies are discovering that hiring AI talent or upskilling existing teams takes much longer than anticipated. Why the Slowdown Might Be Illusory Enterprise Sales Cycles Are Finally Kicking In The most compelling explanation for the apparent plateau has nothing to do with demand and everything to do with procurement realities.

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AI Payment Services Payments Scale 281

SaaStr

FEBRUARY 25, 2025

The event is strategically designed to facilitate 1000s of meaningful connections through 1000+ on-site “Who Do You Want To Meet” dedicated 1-on-1s for B2B founders and execs (no service providers, sorry!) VIP Networking app for B2B founders and execs attending (no service providers, sorry!)

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Sales Recruiting Scale CTO Hire Sales Hiring 195

SaaStr

FEBRUARY 2, 2025

Top Posts: #1: Its 2025 And Even Salesforces Sales Team is Kind of Phoning It In (At Least Some Of It) #2: The #1 Reason SaaS Companies Stall Out at $15m-$20m ARR #3: AI is the Best Thing to Ever Happen to SaaS. Its Unlocking Even More Budget #4: Whats Really Going in Venture Today: Deals Are Down, But Big AI Dollars Are Up.

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AI Sales Hiring Scale B2B 157

SaaStr

JULY 14, 2025

Two of the most misunderstood concepts in AI for B2B and SaaS aren’t technical—they’re human. When SaaStr sent 4,495 AI SDR emails and achieved top-tier response rates, it wasn’t because they flipped a switch—it was because they treated AI training like hiring a human. The reality?

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AI Scale Artificial Intelligence Technical Review 175

Sales Hacker

DECEMBER 17, 2024

The GTM Podcast is available on any major directory, including: Apple Podcasts Spotify YouTube Guy Yalif is a seasoned B2B SaaS executive with over 20 years of go-to-market experience. 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. Youre not alone.

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Scale Engineering Acquisition Scaling 101

Buffer Resources

AUGUST 6, 2024

Before they hire you, they want to understand if they can trust you and get a taste of what you’d bring to the table if you worked together.  I always say that businesses need to prioritize thought leadership the same way they do sales and other forms of lead generation because they go hand in hand. 

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Social Media Business Leadership Sales Hiring 118

Sales Hacker

JUNE 27, 2025

What this means: If you’re hiring: design for lean, AI-leveraged teams from the start. Mary Meeker highlights a shift to real-time expectations across B2B and B2C. Emergence has released the second edition of Beyond Benchmarks , sharing fresh data on how 560+ B2B SaaS companies are navigating disruption.

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AI Search AI Artificial Intelligence Scale 91

Stax

JUNE 3, 2025

Contact sales What is a SaaS Platform? Invest in scalable sales and marketing channels Growth doesn’t mean doing everything at onceit means doing the right things at scale. For B2B SaaS companies, aligning sales and marketing teams is critical. Q: Should I build the payment integration myself or hire a third party?

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Payment Services DevOps as a Service SaaS Payments Payments 88

Sales Hacker

NOVEMBER 8, 2024

For B2B SaaS companies, building a base of advocates – customers who champion your brand can be a pivotal go-to-market advantage. GTM 120: Avoid the AI Sales Skills Atrophy Trap with Peter Kazanjy Pete Kazanjy is a serial founder, and seasoned early stage Saas executive, advisor, and investor.

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Scale Sales Recruiting Sales Hiring AI Search 110

SaaStr

MARCH 6, 2025

His unique position spans both product and business functions including sales, marketing, and customer success – giving him a holistic view of bringing outside perspectives into product development. “The biggest fallacy in tech is that the only way to scale is through hiring and delegating,” notes Nangia.

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AI Scale Sales Hiring Technical Review 219

Sales Hacker

JUNE 17, 2025

At Procore, he led all customer-facing functions—Sales, Marketing, CS, RevOps, and BD. He’s now an investor, advisor, and board member to iconic B2B SaaS companies, and one of the most respected voices in GTM for vertical SaaS. It’s the one person that can hire or fire you. TriNet exists to make that easier.

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AI Technical Advisors Underperforming Technical Team Sales Hiring 84

Sales Hacker

JULY 11, 2025

Managing ops without a dedicated RevOps or CS ops hire. Build a custom GPT copilot If you’re juggling things like hiring, pipeline recaps, creating investor or board updates and it all lives in your head (or in GSheets, Notion, etc.) Use this when you’re: Drowning in recurring internal work. Top takeaways here.

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AI Search AI Scale Sales Recruiting 79

How To Buy Saas

FEBRUARY 25, 2025

Introduction: Why Choosing the Right CRM Matters Choosing the right Customer Relationship Management (CRM) platform can make or break your businesss growth trajectory. A powerful CRM helps organize customer data, streamline sales pipelines, and automate marketing ultimately boosting revenue. Can model complex sales orgs and processes.

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Scale Underperforming Technical Team Technical Review Marketplace as a Service 52

OpenView Labs

NOVEMBER 21, 2023

Instead, consider hiring a sales team and creating inbound marketing channels. That internal collaboration also creates a longer sales cycle here that hinders a viral spark. If you’re B2B, your conversion rate should be even higher since you likely have fewer people entering your funnel.

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Scale Benchmarks Sales Hiring Retention 52

SaaStr

APRIL 24, 2025

conversations with B2B executives. Now our AI is making product recommendations Did not expect this A strong AI will do many things you did not expect pic.twitter.com/ARUg3jXoHr — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) April 24, 2025 So our SaaStr AI is new but its already done over 30,000 (!)

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AI Sales Hiring B2B Artificial Intelligence 185

Sales Hacker

JUNE 20, 2025

People post in our Slack channel that they’re hiring but it’s not posted. And in a world of layoffs, AI disruption, and hiring freezes, your next opportunity will increasingly come through backchannels, not applications. The hiring landscape is shifting. 80% of exec-level jobs never hit job boards. It’s a crazy market.

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Sales Hiring Sales Recruiting AI Search Scale 99

SaaStr

JULY 15, 2025

Their AI has also handled over 139,000 conversations in its first few months, doing everything from reviewing VC pitch decks to managing speaker submissions to advising on hiring decisions. The Training Investment: Plan to spend at least two weeks of intensive training, just like onboarding a new hire. The upside?

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AI Sales Hiring Scale B2B 238

Sales Hacker

MARCH 4, 2025

Pursuit helps companies hire elite go-to-market talent on a non-retainer basis. As a key GTMfund partner, they equip sales and marketing teams with top performers. If you’re hiring for sales or marketing roles, reach out to Pursuit at pursuitsalessolutions.com/gtm or message a GTMfund team member. Is it 50 50?

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Scale Scaling Sales Hiring Technical Review 74