SaaStr

FEBRUARY 11, 2021

In SaaS, #1 most common misfire, with a bullet, is the VP/head of sales. It goes something like “You’ve Got to Get Past the Carcass of Your First VP of Sales” or “It’s The Second VP of Sales When You Really Start Selling” or variants thereof. Because in SaaS start-ups, it seems like the majority of first VP Sales fail.

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SaaStr

JANUARY 24, 2023

During the Boom Times of late ’20-early ’22, we all often confused Taking Risks in hiring … with Just Plain Ignoring Flags. The best VPs of Sales I’ve hired were Directors of Sales before. That’s far better in my experience than hiring a random top tier university grad.

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SaaStr

MAY 22, 2025

Dear SaaStr: How Can I Crush a VP of Sales Interview? To nail a VP Sales interview, you need to demonstrate that youre not just a smooth talker with a great LinkedIn profileyou need to show youre the real deal. Heres how to crush it: Actually Know the Product Before the Interview.

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SaaStr

SEPTEMBER 20, 2024

What are the top 10 mistakes founders are still making today when hiring their VP of Sales? SaaStr CEO and Founder, Jason Lemkin, has done numerous surveys now that confirm that a startling 70% of first hires don’t make it. In this post, we’ll delve into the common pitfalls founders encounter when hiring a VP of Sales.

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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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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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SaaStr

MAY 24, 2022

Many mediocre hires were made to fill slots, reference checks not made, etc. What we used to do, from ‘05-‘19: Do 30 interviews per position, ideally. Then when everything super boomed in 2H’20 and ‘21 it went kind of like this: Do 3-4 solid interview for a position, not 30. So did startups. jasonlk) May 23, 2022.

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SaaStr

MAY 6, 2021

A CRO owns and directs the strategy over a company’s revenue cycle, but there’s not a set standard for operational or management decisions: in addition to sales and sales development, they might be responsible for customer success, lead generation and pipelines, and even marketing and brand development. Is a CRO right for you?

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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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SaaStr

FEBRUARY 29, 2024

If a sales exec makes it anything but effortless to schedule a job interview with them, Basically it won't work out — Jason ✨Be Kind✨ Lemkin  ?? jasonlk) February 13, 2024 So I remember years ago I went to hire my first VP — ever. Recruiting is sales. But for in-bound candidates?

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Sales Recruiting Sales Hiring Interviewing Sales 260

SaaStr

MARCH 22, 2022

This requires effort from your entire organization, and Handshake VP, Employer Partnerships Jessica Peluso outlines some changes that you can make to your brand, and your application, interview, and offer process that will help find the talent you are trying to attract and hire. Below is the transcript of Jessica’s session.

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Sales Hiring Sales Recruiting Scale Sales 261

SaaStr

MARCH 3, 2023

At SaaStr APAC 2023, Scott Pugh, VP of Sales at Figma, shared how to scale these two sales teams while building culture. Pugh’s strategy is simple, albeit not always easy: Recruitment — how to hire the best talent to scale your sales organization. Let’s look at five tips to consider for successful recruiting.

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SaaStr

AUGUST 26, 2020

Founder-led sales generally stops scaling around $1m-$2m ARR. A sign to hire a real sales leader. Over the years at SaaStr we’ve talked a lot about hiring a great VP of Sales, when it works, when it does, and how it moves the needle. The distraction of building a real sales team isn’t worth it yet.

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Sales Hiring Sales Recruiting Scale Sales 326

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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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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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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Tom Tunguz

JULY 25, 2020

In interviewing great CMOs , the product marketing leader is the first marketer most startups should recruit, and often the first key mishire. Product marketing is the vital work of developing a customer lifecycle journey, pricing, sales support materials, analyst relations, and press. This makes sense.

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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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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 177

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

Tom Tunguz

NOVEMBER 16, 2015

As he told me a few days ago, he has observed the lack of sales management and sales execution skills as one of the most consistent deficiencies limiting the potential of early stage SaaS companies. Sales execution deficiency manifests itself at roughly the same time as product market fit.

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SaaStr

JANUARY 21, 2021

We’ve talked a lot about hiring a VP, Sales. 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. In those cases, no “big mistake” hire was made. But still, some hires didn’t work out.

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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. The three things that led to ramping up sales at Flock Safety were: Achieving product-market fit.

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Sales Recruiting Sales Hiring Scale Sales 234

SaaStr

OCTOBER 3, 2023

Interviewing? One bit of advice: Please, please, actually research the company you are interviewing at. The other day I did a similar final, fourth round interview for a VPM. I ended the interview (politely) after 10 minutes and told him to watch the video. Looking for your next role? Been through a lay off? For real.

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SaaStr

JUNE 21, 2023

They hired their first VP of Sales with a wonderful pedigree and experience at some of the hottest startups. because they needed to rebuild the sales team. They rebuilt the sales team and closed some big deals. The lesson — Don’t hire someone just because they have a great pedigree. A good recruiter is worth it.

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Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 293

SaaStr

FEBRUARY 25, 2025

Finding and recruiting top talent is consistently ranked as one of the biggest challenges for growing SaaS companies. SaaStr Annual attracts thousands of high-quality SaaS professionals across functions like engineering, product, marketing, sales, and customer success. Competitive Intelligence and Market Insights and New!!

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SaaStr

OCTOBER 5, 2020

There’s a common thinking that sales teams should be relatively high churn. That the bottom 15-20% of the sales team almost has to churn each year, because it’s survival of the fittest. At Salesforce, at Box, the bottom end of the sales team churns out each year. First, do sales reps really compete with each other?

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SaaStr

OCTOBER 25, 2023

For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. In this interview, David Sacks talks about how 70-80% of investor time is spent looking at AI.

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FastSpring

FEBRUARY 6, 2025

If you’re running a smaller digital business, you may find it challenging to hire great talent. In this episode of Growth Stage, we interview Lizzie Mintus Founder and CEO of Here’s Waldo Recruiting and host of The Heres Waldo Podcast about her thoughts on: The most effective recruiting strategies for SMBs.

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The Angel VC

APRIL 1, 2017

At the excellent SaaStr Annual 2016 conference about a year ago, a very experienced SaaS CEO said on stage that an internal recruiter can be a startup CEO’s secret superpower. I couldn’t agree more, and I think startups should make that hire sooner rather than later. Let’s say you want to hire 10 people in the next 12 months.

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SaaStr

JULY 29, 2021

Someone great at something core you aren’t: Sales, Engineering, Marketing. Great at sales. Do at least 20–30 customer interviews before you start writing too much code. 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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SaaStr

DECEMBER 1, 2023

Hiring a VP of Sales isn’t new, but the conversations have evolved as the world has. SaaStr’s own Jason Lemkin shares the top 10 mistakes he sees during the hiring process during Workshop Wednesday, held every Wednesday at 10 a.m. The last 18 months have seen the biggest changes in the VP of Sales in his SaaS career.

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Kellblog

FEBRUARY 16, 2022

The other day a founder asked me about interviewing because a candidate had described me as “a great interviewer,” and she wanted to know why. I find interviewing and recruiting difficult, have made plenty of mistakes over the years, and the consequences of those mistakes are invariably painful.

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SaaStr

JUNE 24, 2022

Your best sales reps can close so much more than your average rep. Move the bottom 10% out and give the best leads to your top performer, and watch sales go up 20%. The best VPs of Sales design comp plans so the team never wants to leave. You should be striving for zero voluntary attrition on your sales team.

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SaaStr

OCTOBER 28, 2022

In the first session of the eye-opening CRO Confidential series, SaaStr CEO Jason Lemkin interviews Founders Fund Partner Sam Blond about the current economic climate. However, don’t this doesn’t mean that your sales teams shouldn’t bring in more revenue –– quite the opposite.

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SaaStr

JUNE 27, 2024

As it grows, it changes significantly, especially as you move from hiring people who can do everything to hiring more specialized roles. Job Stopped Participating in Every Interview Early On Many founders still interview everyone when their company is at 200 or 300 people. And it was true.

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Sales Hacker

JUNE 10, 2021

There’s one thing recruiters are unanimous about. It’s that sales representatives are one of the toughest positions to hire for. The demand for sales reps is one of the highest of any job. Our recruitment team at EASI has gotten really good at this. Sales courses are largely absent from college curricula.

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