SaaStr

JANUARY 30, 2021

One of the starkest differences I see between First Timers in SaaS and Second Timers is when they hire their VP of Marketing. They often hire a VP of Demand Gen Marketing even before they have their first paying customers. But it’s very, very easy to make the hire late. Second Timers know. But she can help.

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Sales Hiring Sales Recruiting Scale Marketing 351

SaaStr

NOVEMBER 2, 2023

So we’ve spent a ton of time over the years on SaaS talking about hiring a great VP of Sales. Not only because it really matters, but because hiring the wrong VP of Sales can set you back a year — or longer. Don’t make this hire. 50% of what a VP of Sales really does is recruiting.

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Sales Hiring Sales Recruiting Sales Interviewing 296

SaaStr

NOVEMBER 19, 2020

IME, rough order to make hires in: VPM: $0.2m He asked which to hire first. If you have a few nickels in the bank, and you somehow find a great VP a half stage or even full stage early, just hire her. Hiring is so hard as it is. Make the hire now. ARR VPS: $1-$1.5m More here: [link].

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Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 363

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 24, 2025

Dear SaaStr: I’m Starting as a New VP of Sales. A new VP of Sales can add value immediately by focusing on a few critical areas that drive results and demonstrate leadership from day one: Assess and Support Top Performers : A great VP of Sales will immediately identify the top-performing reps and double down on them.

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Sales Recruiting Sales Hiring Sales Leadership 156

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. Meanwhile, SaaS — our tried-and-true darling — is projected at $295 billion with a “mere” 18.4% year-over-year.

AI Search 283

AI Search Artificial Intelligence AI CTO Hire 283

SaaStr

SEPTEMBER 28, 2020

And how often is he recruiting? In fact, every single day he and his team go into their Recruiting War Room, and analyze every single possible recruit coming up the next four years. But in this phase — you need to be Head Recruiter yourself. At first everyone is sort of great at recruiting — by definition.

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Sales Recruiting Sales Hiring Scale Engineering 264

SaaStr

MARCH 6, 2025

One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. 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. Use this updated script for hiring that first VP of Sales.

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Sales Recruiting Sales Hiring Scale Interviewing 177

SaaStr

JUNE 6, 2025

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. From hiring to partnerships to fundraising, being here makes it easier to connect with the right people at the right time. It’s Still the Hub for B2B and SaaS.

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Sales Recruiting Scale Sales Hiring B2B 224

SaaStr

DECEMBER 16, 2020

We’ve talked a lot on SaaStr about how to make that critical hire: the VP Sales. But when you make a mis-hire, it’s about the worst mis-hire you can make. You’ll end up with a crummy sales team under a mis-hire. We’ve posted a script to use when interviewing a VP Sales.

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Sales Recruiting Sales Hiring Sales Engineering 360

SaaStr

MAY 24, 2022

Many mediocre hires were made to fill slots, reference checks not made, etc. If there really is a slowdown (and I’m not sure will be in SaaS), folks will have to work harder. So I’m not yet convinced times are really tougher for SaaS companies. Everyone talks about making 10x hires, and each hire being better than the last.

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Sales Hiring Sales Recruiting Interviewing Startup 315

SaaStr

NOVEMBER 25, 2020

We’ve talked a lot on SaaStr about how to hire a Great VP of Sales. And we’ll keep talking about it — so long as 70% of first-time VPs of Sales don’t make it 1 year. Reason #1 is jumping to Stretch VP of Sales one stage too early. Not hiring people better than you. Do not do this.

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SaaStr

NOVEMBER 5, 2020

One of the biggest challenges in scaling a SaaS company has always been VP and SVP level talent. The companies that create the SVPs you’ll need, especially in Sales and Marketing, are still mostly based in the SF Bay Area. But for now, if you are beginning to scale, aggressively recruit that Bay Area VP you always wanted to hire.

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Sales Hiring Sales Recruiting Scale Scaling 348

SaaStr

MARCH 5, 2025

In our most recent episode of CRO Confidential , hosted by Sam Blond , Graham Moreno , VP of Worldwide Sales at Codium, shared invaluable insights on what drove this growth, the challenges they faced, and how other SaaS companies can replicate this success. Their strategy?

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Sales Hiring Scale Sales Recruiting AI 176

SaaStr

MARCH 3, 2023

There are two types of SaaS companies in the world: those that are category creators and the challengers of incumbent technology. At SaaStr APAC 2023, Scott Pugh, VP of Sales at Figma, shared how to scale these two sales teams while building culture. Let’s look at five tips to consider for successful recruiting.

Scale 268

Scale Sales Recruiting Sales Hiring Scaling 268

SaaStr

JUNE 14, 2020

One of the biggest changes since we started SaaStr is the massive number of SaaS veterans out there. The decade-long run of next-generation SaaS start-ups, and the explosion since 2015 of SaaS unicorns and decacorns has led to a lot of experienced execs on the market. Because SaaS is hard. This is great.

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Sales Hiring Scale Sales Recruiting SaaS 297

SaaStr

FEBRUARY 1, 2021

That you absolutely, positively, have to only hire “Rockstars” in your startups. If you don’t think you need a great VP of Sales, Product, Marketing, Customer Success, and Engineering — then all that all that means is you’ve never worked with a great one. We’re just not far enough along in SaaS 3.0

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Sales Hiring Part-Time VPE Scale Sales Recruiting 278

SaaStr

JANUARY 8, 2022

We’ve talked a lot on SaaStr about how to hire a Great VP of Sales, and how you have to close the first 10 or so customers yourself, and how when you do go to hire your first sales rep — make sure you hire two. But how do you get those first few reps right, when you haven’t made the hire before?

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Sales Recruiting Sales Hiring Sales Pricing 278

SaaStr

JANUARY 21, 2020

Justin Welsh, former SVP of Sales at PatientPop explains how he started in SaaS in 2009 as the second sales hire at Zocdoc. Justin used Sales Culture to grow a successful PatientPop team to 140 employees and 55 million in revenue. Justin Welsh | SVP Sales @ PatientPop. Want to see more content like this?

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Sales Recruiting Sales Hiring Scale Sales 331

SaaStr

OCTOBER 27, 2022

In SaaS, I think one of the biggest traps you can get yourself into as a founder is doing Low ROI things for one minute longer than you have to. But quickly, in SaaS, it becomes worse. Why didn’t we just hire another 3 guys in TechOps much, much. I was lucky to have a great hire who handled our first few large customers.

Sales Hiring 286

Sales Hiring Sales Recruiting Scale Scaling 286

SaaStr

SEPTEMBER 17, 2020

Director+ of Sales at Slack / Zoom / DropBox / Pick Your Brand Name SaaS Company. Because it’s not ARR growth or even an IPO alone that determines if a VP of Sales him or herself is great. And there were probably 100+ RVPs of Sales at that point. Because often, the managers were given a team, or a lot of it.

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Sales Recruiting Sales Hiring Sales Interviewing 306

Tom Tunguz

JULY 25, 2020

But I see this company structure more frequently across SaaS startups. In interviewing great CMOs , the product marketing leader is the first marketer most startups should recruit, and often the first key mishire. By hiring two focused people, the startup is free to find the best person in each role. This makes sense.

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Sales Recruiting Product Marketing Scale Sales Hiring 246

SaaStr

JANUARY 27, 2021

We’ve talked a ton on SaaStr over the years on how to make sure your VP of Sales and top hires really work out. We can pretty much summarize a lot of it into the following: Your VP of Sales should have lots of experience selling at your average ACV. for that type of sale. That they are the right ones.

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Sales Recruiting Sales Hiring Scale Sales 328

SaaStr

JANUARY 5, 2024

In the latest episode of CRO Confidential, host Sam Blond, partner at Founders Fund and former CRO at Brex, sits down with Ashley Kelly, VP of Global Sales Development at Rippling. For context – Ashley had previously helped Sam scale Brex’s outbound sales from $2M to over $300M in ARR as Senior Director of SDR.

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Sales Hiring Sales Recruiting Scale Outbound Sales Team 305

SaaStr

MARCH 24, 2020

Nothing matters but recruiting and using your personal network. Sam Blond, CSO at Brex explains why recruiting, networking and employee happiness is the key to this playbook on recruiting your sales team. Sam Blond | Chief Sales Officer @ Brex. I’m doing The Playbook To Recruiting Your Sales Team.

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Sales Recruiting Sales Hiring Scale Underperforming Technical Team 186

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. I don’t know about you, but I’ve had to recruit a lot of types of folks over the years where my domain knowledge was limited. I’ve had to recruit Ph.Ds.

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Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 255

SaaStr

OCTOBER 22, 2020

Recently, a good friend of mine running a Hot SaaS Start-up asked me if he should hire a particular VP of Product candidate I knew well. The team he’d be managing was a big thumbs up on him. Just don’t hire her. This was for a VP Sales position for a fast-growing SaaS company at about $4m in ARR.

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Sales Hiring Sales Recruiting SaaS Sales 249

SaaStr

FEBRUARY 12, 2022

What was the first warning sign your VP of Sales wasn't going to work out? A lot of veteran SaaS revenue leaders protested, but most of them, upon reflecting on it, came to agree the point was right. A new VP of Sales doesn’t always double sales in 30 days — although it can happen in SMB sales.

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Sales Recruiting Sales Hiring Sales SaaS 269

SaaStr

SEPTEMBER 25, 2020

379: From how many reps to hire, to compensation models, here are the top 10 mistakes founders make when hiring their first sales teams and how to avoid them. Announcer: In today’s SaaStr Insider, SaaStr CEO and founder, Jason Lemkin, shared the top 10 mistakes founders make when hiring their first sales team.

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Sales Hiring Sales Recruiting Scale Sales 240

SaaStr

JANUARY 21, 2021

We’ve talked a lot about hiring a VP, Sales. It’s just such a critical accelerate-or-decelerate decision for a post-Initial Traction SaaS company. We’ve talked about the 48 Different Types of VP Sales , What a VP Sales Really Does , and a Script to Use When Interviewing a VP Sales.

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SaaStr

JANUARY 31, 2022

Having learned from thousands of customers and prospects, Sarah Lash, Envoy’s head of enterprise sales, will talk about what it takes to guide and scale enterprise sales programs during an uncertain future. In my first six months at Envoy , I grew the sales team from six to 17. Combine Strategies To Drive Sales.

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Sales Recruiting Sales Hiring Scale Enterprise 246

SaaStr

JUNE 21, 2024

Sam Blond, the former CRO at Brex with 15 years in tech sales, took the stage at SaaStr Europa 2024 to share nine easy sales concepts that so many get wrong. Sam got his first job in tech sales as an SDR for Jason Lemkin’s company, EchoSign, which later sold to Adobe and launched his career. They did this right at Brex.

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Sales Recruiting Sales Hiring Scale Outsourced Development 284

SaaStr

FEBRUARY 25, 2025

Unparalleled Networking Opportunities SaaStr Annual brings together thousands of SaaS, Cloud and AI executives, founders, VCs, and industry leaders under one roof across our 40+ acre campus, May 13-15 in SF Bay! Finding and recruiting top talent is consistently ranked as one of the biggest challenges for growing SaaS companies.

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Sales Recruiting Scale CTO Hire Sales Hiring 190

SaaStr

SEPTEMBER 8, 2024

When building a list, try to define your potential customer as granularly as possible – size, location, industry, ideal buyer, sales process, technology stack, etc. This will allow you to be much more targeted with your messaging when reaching out and will help you optimize your sales funnel. Pricing is always evolving.

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Sales Recruiting Scale Venture Capital Sales Hiring 317

SaaStr

MARCH 18, 2021

We’ve talked a lot about hiring a VP of Sales at SaaStr , and if you hire a stretch VP of Sales (as most of you will) … how much you can stretch. A related question is — just how quickly can you gain the requisite experience to be a true first time VP of Sales? Had about 8 mos.

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Sales Hiring Sales Recruiting SMB Sales 294

SaaStr

MARCH 5, 2021

Flock Safety’s Founder and CEO, Garrett Langley, and its VP of Growth, Alex Latraverse, know a bit about sales. Enough to go from 0 to 100 sales reps in about 18 months — and they’re looking to be well beyond 100 by the end of this month. Flock Safety is a hardware-enabled SaaS company dedicated to stopping crime.

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Sales Recruiting Sales Hiring Scale Sales 247

SaaStr

MARCH 18, 2025

” – Colin Jones, CRO Emeritus at Wiz You may have seen the news that Google is making its biggest acquisition — by far — of Cloud and SaaS security leader Wiz for a stunning $32 Billion (!). Rather than seeing this as a liability, Wiz leveraged it as a strategic advantage — even in its sales team.

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Scale Sales Hiring Scaling Sales Recruiting 176