SaaStr

JANUARY 24, 2025

Even in 2025. One thing is clear is the team that send this isnt the A or B sales team. And a great example of running a very successful outbound program at scale here: And what I’d do better. So below is an email I got from the Slack team at Salesforce. Its just mid. Its pretty bad. Zero personalization. How inviting!

Scale 278

Scale Sales AI Enterprise 278

SaaStr

MAY 26, 2025

So what does that mean for inside sales? A 50/50 Sales Team. At least for SMB and more routine mid-market sales. By 2026, these same AI systems will have evolved to manage entire sections of the sales process autonomously. But you can automate 30%-40% of support for real … with top 10% CSAT. 50% are AI. Just fewer.”

Scale 236

Scale Sales Hiring AI Sales 236

SaaStr

MAY 1, 2025

Your first few sales reps have to be … different. And someone you can trust with your few, precious leads. "That "That early sales team … they have to be product gurus. Leads are too precious in the early days to waste on someone you dont trust to clos. A bit of a product savant. Are They Resilient?

Sales Hiring 256

Sales Hiring Scale Sales Interviewing 256

SaaStr

FEBRUARY 7, 2025

In the latest episode of SaaStr’s CRO Confidential Series, our host Sam Blond sits down with Ron Gabrisko, CRO of Databricks , to unpack the journey from $1M in ARR to crossing $3B ARR at the end of January 2025. His view is your sales team teaches your customers how to get value out of your product.

Scale 169

Scale Sales Hiring Scaling Revenue 169

SaaStr

MAY 20, 2025

Convergent evolution from 2 very different start-ups that now have many similarities at scale. HubSpot has achieved jaw-droppinggrowth with a 29% revenue CAGR from Q1 2019 to Q1 2025, growing from $152M to $714M quarterly revenue. HubSpot has twice the revenue (and thus twice the ARPU), but also was founded 6 years earlier.

SMB 267

SMB Scale Education AI 267

SaaStr

JUNE 15, 2025

Dear SaaStr: How Do I Hire a Great First 1-2 Sales Reps? "Never, ever hire a VP of Sales until you have 2 individual sales reps really closing. . "Never, "Never, ever hire a VP of Sales until you have 2 individual sales reps really closing. And that early sales team? Hitting quota.

Sales Hiring 231

Sales Hiring Scale Sales Compensation 231

SaaStr

JUNE 19, 2025

Dear SaaStr: How Do I Get a Job as a First Time VP of Sales? If you’re aiming to land a VP of Sales role, you need to position yourself as someone who can deliver results and scale a team. "The "The biggest mistakes CROs and VPs of Sales make when they take a new role." Highlight your ability to scale.

Sales Recruiting 212

Sales Recruiting Sales Hiring Scale Development Team Review 212

SaaStr

APRIL 14, 2025

SaaStr Annual has always been the go-to event for SaaS founders, executives, and investors, but 2025 is shaping up to be the best one yet. 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! 100+ scale-ups and start-ups showing you how they do it!

VP of Engineering 201

VP of Engineering CTO Coach VPCs (Virtual Private Cloud) Scale 201

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.

Sales Hiring 231

Sales Hiring Underperforming Technical Team AI Scale 231

SaaStr

DECEMBER 26, 2024

Gong has its 2025 State of Revenue out. That ties to our overall rough sales cycle data here: Dear SaaStr: What’s a Good Benchmark for B2B Sales Cycles? Is usually see 15%-20% as start-ups scale, but 25% is probably the right target as you scale. You can grab it here. Thats a bit higher than I expected.

Scale 278

Scale Benchmarks B2B Enterprise 278

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. The numbers are staggering: AI spending is set to hit $644 billion in 2025, growing at a mind-bending 76.4% year-over-year.

AI Search 283

AI Search Artificial Intelligence AI CTO Hire 283

SaaStr

JUNE 7, 2025

as of April 2025, the growth trajectory has flattened since late 2024. I pay more for AI subscriptions than I do for my car lease — Matthew Berman (@MatthewBerman) June 5, 2025 Why the Slowdown May Be Real Several structural factors suggest this isn’t just a temporary pause: Implementation complexity has caught up with enthusiasm.

AI 274

AI Payment Services Payments Scale 274

SaaStr

JANUARY 12, 2025

Top Posts: #1: 2025 And The Rise of the Mech AE (Account Executive) #2: 2025 Should Be Better Than 2024 For Almost All Leading Public SaaS Companies #3: 38% of Bootstrapped Start-Ups Have Solo Founders. But Only 17% of VC-Backed Ones Do. And 10%-12% of Ones That IPO. #4:

Sales Hiring 273

Sales Hiring Scale Scaling Revenue 273

SaaStr

JANUARY 19, 2025

So one big theme of 2025 SaaStr Annual (May 13-15 in SF Bay) will be going deep on Vertical SaaS. We’ll hear from the CRO of $3B Clio (legal SaaS), the CEO and CRO of Flock Safety (police and safety SaaS), and dozens of others on how to scale their vertical SaaS industries and platforms. See you there! How Kyle does it here: #3.

Scale 189

Scale Sales Hiring Scaling SMB 189

SaaStr

JUNE 9, 2025

After years of drought, 2025 has delivered a scorching hot public market for tech companies so far, with some eye-popping returns that should have every SaaS founder and investor paying attention. The IPO window isn’t just cracked open—it’s wide open. The most recent five IPOs are averaging 121.5%

B2B 177

B2B Marketing Scale Benchmarks 177

SaaStr

JANUARY 5, 2025

Top Posts: #1: Why The Greatest Sales Teams Just Kill It On Dec 31. But in 2025, Step Up or Step Aside. #4: 2025 Will Be Radically Different. . #4: 2025 Will Be Radically Different. When Everyone Else Has Gone Home. #2: 2: Gong: $100k Deals Take About 70 Days to Close #3: Yes, You Need to Focus.

Scale 269

Scale AI Scaling SaaS 269

SaaStr

JUNE 25, 2025

AI and Cybersecurity: How Rubrik’s Co-Founder Built a $1B+ ARR Platform While Joining the AI Revolution Lessons from Arvind Nithrakashyap, Co-Founder and CTO of Rubrik, on scaling cyber resilience platforms, building multiple product curves, and implementing AI across both products and operations.

Cybersecurity 250

Cybersecurity AI Scale CTO Hire 250

SaaStr

MAY 5, 2025

Ok about 2,000 of you have already picked your 2025 SaaStr Annual + AI Summit sessions so far and here are the top sessions … for now: 1. The New Rules of SaaS Growth: Whats Next for AI, PLG, and Revenue Scale with HubSpots CEO 2. Kick-off to SaaStr Annual 2025 with SaaStrs Founder & CEO 4.

Scale 167

Scale New CTO CTO AI 167

SaaStr

JUNE 6, 2025

Big News: SaaStr AI is coming to LONDON 2025 Tickets Just Launched Get ready because this December, we’re bringing the best of SaaStr AI 2025 across the pond to London ! And with the SaaStr AI Summit running alongside, we saw over 200 AI-first startups and scale-ups showcase how AI is reshaping SaaS. Tickets just went on sale.

AI 240

AI Scale Innovation B2B 240

SaaStr

NOVEMBER 29, 2024

Start-ups, scale-ups and public companies in 2021 would hire a lot of folks they just wouldn’t hire today. If you are running the same playbook in 2025 to get a job that you ran in 2021, it probably won’t work. But almost everyone growing even at “pretty good” rates is hiring. In 2021, it was the opposite.

Sales Hiring 278

Sales Hiring Scale Marketing SaaS 278

SaaStr

FEBRUARY 25, 2025

The Best Speakers In The World With hundreds of sessions from proven SaaS leaders who have scaled companies to significant revenue milestones, SaaStr Annual offers practical, actionable insights you won’t find elsewhere. Sessions typically focus on real metrics, strategies, and lessons learned, not theoretical concepts.

Sales Recruiting 190

Sales Recruiting Scale CTO Hire Sales Hiring 190

SaaStr

JUNE 4, 2025

Referrals are Chime’s largest acquisition driver since 2022 , helping bring sales & marketing spend down to 26% of revenue in Q1 2025, from 42% in 2022. Keep Driving Up ARPU, Slowly But Steadily Chime’s ARPU grew from $231 to $251 (Q1 2024 to Q1 2025). million in Q1 2025. 5 Interesting Leanings: #1.

Outsourcing Services 197

Outsourcing Services Scale Banking Customer Lifetime Value 197

SaaStr

JUNE 6, 2025

pic.twitter.com/IPZBNrz1jQ — Sam Altman (@sama) May 21, 2025 Here’s the rationale: #1. 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. — Hurley (@Johnsjawn) May 31, 2025 #4.

Sales Recruiting 224

Sales Recruiting Scale Sales Hiring B2B 224

SaaStr

FEBRUARY 12, 2025

Meet Wyatt Jenkins: From Construction Sites to Chief Product Officer If you want to understand how vertical SaaS companies scale to $1B+ in revenue while staying true to their customers, there’s no better person to learn from than Wyatt Jenkins, Chief Product Officer at Procore Technologies.

Construction 248

Construction Scale SaaS Travel 248

SaaStr

JUNE 29, 2025

How a 20-year-old company found its second wind in the AI era TL;DR : Palantir just posted 39% YoY growth in Q1 2025, marking a stunning turnaround from the 13% growth trough of 2023. The market was questioning whether Palantir’s complex, bespoke approach could scale in a world increasingly dominated by self-serve SaaS.

AI 254

AI Artificial Intelligence Software Review Technical Review 254

SaaStr

NOVEMBER 24, 2024

How to Successfully Bring AI Products to Market at Scale with GitHub’s CRO” # 2. Samsara’s Rise to Vertical SaaS Leader and $1B+ ARR with Samsara’s CEO and Co-Founder” #3 What Really Matters in SaaS in 2025 with Jason Lemkin and Dave Kellogg # 4. Carta: 43.6%

Scale 274

Scale AI Startup Scaling 274

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. The Second “Problem” With Small But Mighty AI Teams … Is Enterprise Sales A tiny team can be fairly efficient with a 100% self-serve and PLG motion.

AI 275

AI Sales Hiring Scale B2B 275

SaaStr

JUNE 22, 2025

This isn’t your typical “here’s what public companies are doing” report – this is real data from real private companies dealing with real challenges in 2025. The Bottom Line: SaaS is Maturing, and You Have to Adapt The 2025 data tells a clear story: The SaaS industry is maturing.

B2B 207

B2B Data Scale Startup 207

SaaStr

JUNE 22, 2025

The IPO market has been … on fire in 2025. ” The Numbers Behind the Filing Navan’s IPO filing comes with impressive scale: Probably close to $500m ARR today, $300M in annual revenue as of 2024 40% average revenue growth , with the fintech business growing 100% and travel business expanding 30% $9.2B

B2B 179

B2B Payments SaaS Payments Payment Services 179

SaaStr

APRIL 20, 2025

B2B Startups Spend 15% of Revenue on Sales and 10% on Marketing, Per SaaS Capital #4. Built a Bottom-Up AI SaaS Without a Single Sales Rep #5. The Top 10 Customer Success Metrics Investors Care About in 2025 with Gainsight CEO Nick Mehta #4. From $1M to $3B ARR: Databricks CRO Ron Gabrisko on Scaling a Revenue Rocket Ship

Scale 144

Scale Customer Success Scaling AI 144

SaaStr

FEBRUARY 7, 2025

At SaaStr AI Day 2025, Jim Palmer, Dialpad’s Chief AI Officer (and co-founder of TalkIQ, which Dialpad acquired), shared the tactical playbook they used to build and scale their AI capabilities. Here are the key learnings every SaaS company should know. The Build vs. Make this decision early.

AI 252

AI Scale Government compliance 252

USIO

JUNE 10, 2025

Let’s dive into why escheatment is still a challenge in 2025—and how Usio makes the process smooth, compliant, and user-friendly. In 2025, people expect faster refunds, better communication, and more flexibility. Brand Loyalty at Stake : Slow or clunky refund experiences can lead to negative reviews or churn. emails or calls.

Payment Solutions 130

Payment Solutions Payment Services PayPal Traceability 130

SaaStr

JUNE 28, 2025

But a very different one from the 2021 wave: Deal volume is surging : 2025 has been a “green light” year for IPOs, with 52 new U.S. Q1 2025 saw 59 IPOs raise $8.9 Growth is #1, but the profitability premium is real : The share of profitable IPO companies at listing surged in the US from 29% in Q1 2024 to 59% in Q1 2025.

Payments 176

Payments SaaS Payments Payment Services AI 176

Clouded Judgement

JUNE 17, 2025

As a public company with significant scale, it’s hard to grow quickly if you have to rely solely on new customers for that growth. Here’s the data: Sales Efficiency: Gross Margin Adjusted CAC Payback Demonstrating the ability to efficiently acquire customers is the fifth aspect of a successful quarter.

Cloud 277

Cloud Software Benchmarks Retention 277

SaaStr

APRIL 8, 2025

Dear SaaStr: When Should I Hire Our First Sales Person, and Who Should I Hire? "The "The one cheat code to making your first sales hires. Because as a founder, you need to understand the sales process, the objections, and what resonates with your customers. Look for at least 18 months of SaaS sales experience.

Sales Hiring 176

Sales Hiring Scale Sales Pricing 176

SaaStr

APRIL 4, 2025

So we’ll have ~20 of the latest AI start-ups from YCombinator at a special YC Demo Pod area at 2025 SaaStr Annual! Come meet them (and also watch 100+ present live at our first AI Demo Stage ) at 2025 SaaStr Annual, May 13-15 in SF Bay!! Businesses use us for customer support, leads qualification, and more.

AI Search 167

AI Search AI Startup Scale 167

SaaStr

MARCH 23, 2025

How Codeium /Windsurf Built A Billion-Dollar AI Company and a Winning Sales Machine #2. The Top 10 Customer Success Metrics Investors Care About in 2025 with Gainsight CEO Nick Mehta #4. The 2025 SaaS Vibe Check: What Founders Need to Know Right Now with SaaStr Founder Jason Lemkin #5. Top Pods and Vids: #1.

Scale 156

Scale AI Sales Customer Support 156