SaaStr

MARCH 16, 2025

Alex Rosenblatt was the first marketing hire and Chief Marketing Officer at Datadog, all the way through IPO and beyond. And see everyone at SaaStr Annual 2025, May 13-15 in SF Bay!! He spent over eight years scaling their marketing from zero to supporting a multi-billion dollar public company. The problem?

Scale 236

Scale Sales Hiring Scaling Marketing 236

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 234

Sales Hiring Underperforming Technical Team AI Scale 234

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." A VP of Sales’ #1 job is building a team.

Sales Recruiting 217

Sales Recruiting Sales Hiring Scale Development Team Review 217

SaaStr

JUNE 15, 2025

Dear SaaStr: How Do I Hire a Great First 1-2 Sales Reps? Hiring your first AE (Account Executive) is a pivotal moment for your startup. "Never, ever hire a VP of Sales until you have 2 individual sales reps really closing. . "Never, And that early sales team? Hitting quota.

Sales Hiring 234

Sales Hiring Scale Sales Compensation 234

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. An A+ AI will soon join every sales call, for real. You’ll Need to Manage Both.

Scale 240

Scale Sales Hiring AI Sales 240

SaaStr

FEBRUARY 8, 2025

Every great hire starts before their first day And often even during the interview process — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) January 12, 2025 #1. The Best VPs Start Before They Start The best sales leaders start reaching out to a few great customers they already know. starting. #2.

Sales Hiring 259

Sales Hiring Interviewing Sales Marketing 259

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.

Scale 251

Scale AI Sales Hiring Sales 251

SaaStr

NOVEMBER 29, 2024

It’s not the crazy hiring market of 2021. He just can’t find enough great folks to hire. It earned them special attention from others on the hiring panel + company leaders… — Brie Wolfson (@zebriez) November 26, 2024 Everyone great is hiring. But almost everyone growing even at “pretty good” rates is hiring.

Sales Hiring 278

Sales Hiring Scale Marketing SaaS 278

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

APRIL 8, 2025

And thus — hiring more. They they are doubling down and hiring even more to keep these gains going. but close enough) AND they then double their hiring … now they are moving 4x as quickly. And can it sell and scale sales? The first one is that it’s a competitive world. In a handful of months!

AI 276

AI Sales Hiring Scale B2B 276

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 274

AI Search Artificial Intelligence AI CTO Hire 274

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 275

AI Payment Services Payments Scale 275

SaaStr

FEBRUARY 1, 2025

When I look at the VP of Sales / CRO that didnt work out the past 12-18 months across the SaaStr Fund portfolio and my ecosystem, one thing stands out. And its an old SaaStr theme: #1: You have to hire folks in sales where their last job was harder. There may exceptions at rocketships. You often fly. Voice APIs?

Sales Hiring 179

Sales Hiring Sales compliance Interviewing 179

SaaStr

FEBRUARY 25, 2025

SaaStr Annual attracts thousands of high-quality SaaS professionals across functions like engineering, product, marketing, sales, and customer success. Many companies strategically use the event to meet potential hires, conduct interviews, and build their talent pipeline. Competitive Intelligence and Market Insights and New!!

Sales Recruiting 195

Sales Recruiting Scale CTO Hire Sales Hiring 195

SaaStr

FEBRUARY 26, 2025

But like many things my views have evolved "The Rise of CRO: The Challenges of Unchecked Growth" @davegerhardt + @jasonlk pic.twitter.com/VL3S6MAFOw — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) June 11, 2024 Three trends have fueled the rise of hiring COOs and CROs closer to $10m ARR than $50M ARR: Faster Growth.

Sales Hiring 207

Sales Hiring Startup Management SaaS 207

SaaStr

JUNE 6, 2025

pic.twitter.com/IPZBNrz1jQ — Sam Altman (@sama) May 21, 2025 Here’s the rationale: #1. Whether it’s hiring a VP of Sales who’s scaled a team to $50M ARR or finding a product leader who’s built enterprise-grade solutions, the talent pool here is unparalleled. #2. — Hurley (@Johnsjawn) May 31, 2025 #4.

Sales Recruiting 225

Sales Recruiting Scale Sales Hiring B2B 225

SaaStr

JANUARY 19, 2025

AI Should Kill Contact Me in 2025. Top SaaStr Posts: #1. Its Long Since Time. #2: 2: Adding AI to SaaS: Inside the AI Product Strategies of Figma, Cloudflare, GitHub and Ramp #3: Crunchbase: 50% of VC Capital Went to SF Bay Last Year, Q4 Roared Back for Venture Capital #4: 8 Quick Ways to Get More High Quality Leads. Right Now. #5:

AI 269

AI Sales Hiring Venture Capital Startup 269

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

JANUARY 26, 2025

Top Posts: #1: The Top 10 Mistakes SaaS Startups Make: The 2025 Edition #2: When You Raise Venture Capital, A Clock Starts Ticking. At First, Softly. Then Louder and Louder. #3: 3: What Works Better for Field Marketing: Small, Intimate Events? Or the Big Mega Industry Events? #4: 4: AI is the Best Thing to Ever Happen to SaaS.

Sales Hiring 227

Sales Hiring Venture Capital AI Startup 227

Clouded Judgement

JUNE 17, 2025

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. In theory, any growth rate is possible with an unlimited budget to hire AEs. I consider >120% best in class for companies selling to SMBs (like Bill.com).

Cloud 277

Cloud Software Benchmarks Retention 277

SaaStr

APRIL 20, 2025

Dear SaaStr: How Should I Actually Set the Sales Plan for the Year For My VP Sales? This is where you build your operational model: sales hiring, marketing spend, product investments, etc. This is critical for managing your burn rate and ensuring you dont run out of cash. Try the C10, C60, and C90 framework.

Sales Hiring 159

Sales Hiring Sales Communication Revenue 159

SaaStr

MARCH 12, 2025

And see everyone at 2025 SaaStr Annual, May 13-15 in SF Bay for 300+ more sessions, workshops, and braindates like this! “Marketing is fluffy and unmeasurable” – Unlike sales, which has clear metrics like quota attainment, founders often believe marketing can’t be measured.

Sales Hiring 195

Sales Hiring Marketing Technical Review Underperforming Technical Team 195

SaaStr

MARCH 6, 2025

One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. All the questions still hold today, but I wanted to update them for 2025. It’s a different world today, AI-fueled, often distributed and hybrid, and with inflation both in titles (CRO or VP Sales) and compensation expectations.

Sales Recruiting 177

Sales Recruiting Sales Hiring Scale Interviewing 177

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! Sekar emphasizes CAC payback period as the single most important metric for product leaders to track.

Scale 257

Scale Transportation Scaling SMB 257

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 Help You Set Goals For New Hires, For Your Sales Team, or Any Department Share where you want to get to and where you are, and ask our AI to draft the KPIs and goals for each department or org to get there #7.

Sales Hiring 157

Sales Hiring AI Interviewing B2B 157

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.

Sales Hiring 95

Sales Hiring Sales Recruiting AI Search Scale 95

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. And we’ve done several great live Workshop Wednesdays with top CROs and VPs of Sales in Vertical SaaS in particular recently that are all A+ and worth watching: #1. See you there! How Kyle does it here: #3. How Kyle does it here: #3.

Scale 189

Scale Sales Hiring Scaling SMB 189

SaaStr

FEBRUARY 26, 2025

pic.twitter.com/RhXYJqZuMg — Marc Benioff (@Benioff) February 26, 2025 Let’s dig in more 5 Interesting Learnings: #1. Only 21% of Salesforce’s Revenue is from … Sales This has been true for many years, but it often comes as a surprise to those that don’t know the company as well as they know its CRM. #2.

Scale 195

Scale Sales Hiring Azure Cloud 195

SaaStr

APRIL 14, 2025

SaaS Capital surveyed 1,000 B2B startups of varying sizes to find out just how much today they are spending in sales and marketing in this new era of efficiency. That full report here: 2025 Spending Benchmarks for Private B2B SaaS Companies The answer? Its not just Marc Benioff hiring more sales execs in the AI era.

Scale 249

Scale Sales Hiring B2B Startup 249

SaaStr

APRIL 13, 2025

As we gear up for 2025 SaaStr Annual, May 13-15 in SF Bay , we wanted to take a look back at one of your favorite SaaStr conversations with Parker Conrad at SaaStr. And come meet Rippling and learn its secrets to building compound products when their VP of Product Anique Drumright joins us on-stage at 2025 Annual !

Startup 152

Startup Sales Hiring Underperforming Technical Team Cloud 152

SaaStr

JANUARY 18, 2023

It’s the most common objection you’ll get in SaaS sales … Not Right Now. It can’t strategically improve sales software, financial software, quoting software, recruiting software, QA processes, call center software, etc. And when you hire a real, great VP of Sales. Truly qualified leads and prospects. I Don’t Have Budget.

Sales Recruiting 306

Sales Recruiting Sales Hiring Technical Review Software Review 306

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.

AI 152

AI Sales Hiring Scale B2B 152

SaaStr

APRIL 24, 2025

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 (!) And come meet them at 2025 SaaStr Annual, May 13-15!)

AI 179

AI Sales Hiring B2B Artificial Intelligence 179

SaaStr

APRIL 7, 2025

the AI got the dates wrong for SaaStr Europa 2025, which is probably because we haven’t launched yet so it’s “guessing”), I just make a quick voice note and the model is almost instantly updated. I’m shocked we don’t already have this for sales calls. This will utterly change how we do sales.

AI 207

AI B2B ChatGPT Scale 207

Payrix

DECEMBER 18, 2024

While many partners excel technically, broader operational considerationssuch as resourcing and support considerations , sales strategies , marketing , and portfolio managementremain areas for growth. Looking ahead to 2025 As 2025 approaches, Ella and Michael offered valuable advice for software companies tackling Embedded Payments.

Payments 130

Payments Embedded Payments Merchant Services Payment Services 130

Sales Hacker

JUNE 13, 2025

2025 is a different world. The venture market in 2025 is more bifurcated than ever. At the Series B stage, Q1 2025 saw more total capital raised than previous quarters, despite fewer deals closing. The median pre-money valuation in Q1 2025 is $16.1M Founders raised rounds in days. Today, capital is still there.

AI Search 86

AI Search Sales Hiring Sales Recruiting Scale 86

SaaStr

MAY 31, 2024

1: How Sales and Marketing Have Shifted Since 2020 Expectations and the types of people working in SaaS have shifted over the past few years, and much more in sales, marketing, and customer success. . #1: He had a friend help him hire an email marketer to send ticket emails to the events. There’s no choice.

Sales Hiring 295

Sales Hiring Sales Recruiting Marketing Scale 295