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 255

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 227

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.

AI 206

AI B2B ChatGPT Scale 206

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 233

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?

AI 276

AI Sales Hiring Scale B2B 276

SaaStr

MAY 27, 2021

For the past 10 years, I’ve been a sales advisor for the portfolio companies of early stage venture capital firm True Ventures. It’s fascinating work for a sales mind like mine that’s focused on helping brilliant people turn ideas into revenue-driving businesses. . In his piece, Jason recommends hiring VPs in a certain order.

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Sales Hiring Scale Venture Capital Sales 238

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

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.

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Scale Sales Hiring B2B Startup 247

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 193

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 203

SaaStr

OCTOBER 9, 2020

A VP of Sales and Success A VP of Sales and Marketing A VP of Sales and Anything Else. Is usually not really a VP of Sales. Sales managers back when I never managed sales. For signs the prospective hire just won’t work out, no matter how strong they might look on paper.

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Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 255

SaaStr

DECEMBER 2, 2023

Dear SaaStr: What Is The Optimal Structure of an Initial SaaS B2B Sales Team? Where, roughly speaking, each sales rep brings in at least 4x-5x the total compensation they take out. Where you burn a ton of cash is “buying” sales. Shoving sales reps into segments where you don’t have enough leads / enough demand.

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Sales Hiring Scale B2B Sales 268

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 283

SaaStr

JULY 14, 2024

Hiring and Interviewing Tips: Jason emphasizes the importance of interviewing at least 30 candidates for a role and consulting with an expert in the field to interview the final candidate. Product-Led Growth (PLG) vs. Enterprise Sales: Jason discusses the evolution of PLG, noting that it’s essentially freemium with better analytics.

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Sales Hiring Outsourcing Services Scale Interviewing 250

SaaStr

AUGUST 12, 2024

Probably the biggest challenge in vertical SaaS I see is scaling the sales team. It’s pretty easy to hire SaaS sales execs to sell … a SaaS sales product. But who do you hire to sell a very complex piece of vertical software? So if you hire reps for standard B2B companies, they often literally close nothing.

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Sales Hiring Scale Sales SaaS 311

SaaStr

JANUARY 27, 2023

As the past few years have demonstrated, it’s wise to expect the unexpected, especially when it comes to hiring. In particular, hiring for your sales team is critical in an uncertain economic outlook. Additionally, sales professionals looking for a new role should choose their next company wisely.

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Sales Recruiting Sales Hiring Scale Compensation 244

SaaStr

MARCH 18, 2024

Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? You’ll be very tempted to hire someone with a seemingly magical rolodex.

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Sales Hiring Sales SaaS B2B 306

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 95

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.

AI 275

AI Payment Services Payments Scale 275

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

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 155

Predictable Revenue

OCTOBER 29, 2020

Even in B2B enterprises, that buyer is a person and we shouldn't forget that. The post The Goldilocks Rule: Making Your First Sales Hire appeared first on Predictable Revenue. Ari Levine has learned to approach everything from the position of the consumer.

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Sales Hiring Sales B2B Enterprise 165

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!)

Sales Recruiting 193

Sales Recruiting Scale CTO Hire Sales Hiring 193

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

MARCH 6, 2023

B2B founders and sales agents feel pressured to keep up with the rapidly evolving market. SaaS companies must implement flexible and innovative sales strategies that can weather the future. The state of B2B sales in 2023 Before creating a dynamic strategy, it is essential to understand the current state of B2B sales.

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Innovation Sales Hiring B2B Strategy 246

SaaStr

OCTOBER 22, 2019

We’ve learn a lot over the years and really we only want to hire folks that know and believe in SaaStr. And ideally, have a mix of B2C and B2B experience. is a really sort of a media/community company, but our consumers and customers are all B2B/SaaS). The post What We Are Hiring for at Team SaaStr! So SaaStr Inc.

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Sales Hiring Scale Social Media B2C 33

SaaStr

MARCH 30, 2025

Dear SaaStr: What’s The Toughest Skill to Learn to Scale in B2B? To constantly, painfully, boring-ly be recruiting the next level of management and managers all the time. By $2m in ARR, you need a VP of Sales, Marketing, Customer Success, Product and Engineering (if you can afford them all). You need them all. "We

Scale 158

Scale Sales Recruiting B2B Sales Hiring 158

SaaStr

JUNE 26, 2023

and 28% from Europe/EMEA So as you can see, the leaders in B2B SaaS are very international. ARR is material and enough to fund the hire and small office. 42% start with a GM of EMEA/Europe, But the Majority Start with a VP of Sales or Marketing for EMEA/Europe. .” #2. Slow it down and make the right hire.

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Sales Hiring Revenue SaaS Scale 353

SaaStr

AUGUST 13, 2024

1: Don’t hire a VP (or anyone in the early days) that you aren’t 95% sure is great. Founders between a million and $250M are talking about lowering the bar for hiring because they aren’t sure if the person is great or they’re trying to fill a gap. A great Head of Sales will move the needle. You can’t do that.

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Sales Hiring Part-Time VPE Venture Capital Fractional VPE 300

SaaStr

MAY 28, 2024

If you’ve read SaaStr or have been around for the last decade, you might be familiar with some of the repeated GTM mistakes founders tend to make, but the world of hiring, people, scaling, and workplace expectations are significantly different today than they were before March 2020. Don’t make the hire. They weren’t getting any leads.

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Sales Hiring Scale AI Search AI 299

SaaStr

SEPTEMBER 28, 2022

Dear SaaStr: What do you look for when hiring a VP of Product for a B2B SaaS? In particular, the dilemma I’m facing is hiring between a SaaS expert or a target market expert. First, I’d go for a SaaS expert over a domain/target market expert in just about any senior hire — VP Product, VP Sales, VP Marketing.

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Sales Hiring B2C B2B Engineering 315

SaaStr

JANUARY 6, 2023

Dear SaaStr: I’m Pretty Hands Off on the Sales Team. What Will I Learn Getting More Involved in Sales? You may think you know this intuitively, but you don’t: You may think sales organizations magically create revenue. You may not understand how critical it is to optimize a sales organization.

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Sales Hiring Scale Sales B2B 262

SaaStr

MAY 25, 2024

Cloudinary VP of Developer Experience Sanjay Sarathy shares his journey to more than $100M and the lessons he learned along the way for building a PLG motion and an Enterprise sales motion. They didn’t initially envision being a large Enterprise sales organization. Let’s first start with how Cloudinary came to be.

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Scale Sales Hiring SaaS Payments Development 306

SaaStr

JULY 29, 2021

Someone great at something core you aren’t: Sales, Engineering, Marketing. Great at sales. It just takes that long in SaaS and B2B, nine times out of ten. If you hire someone to do the first sales, you’ll never understand it yourself. When you go to hire your first sales rep, hire 2.

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Sales Hiring Sales Recruiting Interviewing Engineering 306

SaaStr

MAY 25, 2020

I recently put out a call on Twitter and LinkedIn on folks’ top tip to take friction out of their sales processes. “Presumptive close in a transactional sale. “At “Help people buy how they want to buy and be as transparent as you can with pricing ” – Ken Edwards, Sales leader, Uberflip.

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Sales Hiring Sales Outsourced Development Technical Review 342

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 (!)

AI 178

AI Sales Hiring B2B Artificial Intelligence 178

SaaStr

OCTOBER 10, 2022

From a venture capital perspective, there’s now a premium on driving efficient growth rather than growth at any cost. . “Sales and marketing alignment is a terrific place to figure out and improve efficient growth.” . From the get-go, ensure alignment between sales and marketing teams on goals and anticipated outcomes.

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Scale Sales Hiring Venture Capital Marketing 320