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. Too many VPs of Sales and CROs show up to interviews knowing almost nothing about the product.

Sales Recruiting 197

Sales Recruiting Interviewing Sales Hiring Scale 197

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.

Scale 273

Scale Sales Recruiting Sales Hiring Scaling 273

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?

Sales Recruiting 331

Sales Recruiting Sales Hiring Scale Sales 331

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

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

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.

Sales Recruiting 189

Sales Recruiting Sales Hiring Scale Underperforming Technical Team 189

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.

Sales Hiring 301

Sales Hiring Sales Recruiting SMB Sales 301

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.

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

SaaStr

MARCH 18, 2025

As Colin describes it, “I went to the CEO and asked to generate more revenue and hire more people, which is counter-intuitive to the standard approach where revenue leaders may sandbag to over deliver and crush numbers.”

Scale 180

Scale Sales Hiring Scaling Sales Recruiting 180

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. PLG, enterprise SaaS, marketplaces). And you send the wrong signal to recruiters. It’s a crazy market.

Sales Hiring 97

Sales Hiring Sales Recruiting AI Search Scale 97

SaaStr

JUNE 26, 2023

Dear SaaStr: What’s the Best Way to Get Ahead in SaaS Sales? It is important to decide which of 3 life tracks you want to be on: Super-successful sales rep / individual contributor. Successful sales manager. I.e., become a VP of Sales someday. Leverage “sales” to become a founder, business owner , etc.

Sales Recruiting 261

Sales Recruiting Sales Hiring Sales SMB 261

SaaStr

DECEMBER 10, 2020

I hear again and again from SaaS founders growing to $5m, $10m ARR or even more that they don’t need a certain VP — with the exception of a VP of Sales. Basically, in SaaS, everyone “gets” that they need a VP of Sales. Hire not just 1-2 reps, but 10. I Need a VP of Sales. Manage a trade show?

Sales Hiring 363

Sales Hiring CTO Hire Sales Recruiting Scale 363

SaaStr

MARCH 25, 2023

So one recent survey we did really brought out a healthy debate: does your VP of Sales really need to be a product expert? Many of the comments said it was more important a VP of Sales understand process and leadership more than the product itself. Then I say … you probably made a mis-hire. They often melt. Be present.

Scale 291

Scale Sales Hiring Sales Recruiting Sales 291

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?

Scale 293

Scale Sales Hiring Sales Recruiting Sales 293

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.

Sales Recruiting 293

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 293

SaaStr

MARCH 7, 2021

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. Yes, you can manage the sales team yourself. You can do this.

Part-Time VPE 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

SaaStr

JANUARY 27, 2021

“Give the VP of Sales More Time” This is always terrible advice. If a VP of Sales can’t improve things in one sales cycle or less — she never will. In one sales cycle, or less. Don’t hire some junior marketing person that can’t really get you more leads. More on that here.

Part-Time VPE 348

Part-Time VPE Sales Hiring Scale Sales Recruiting 348

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. Lead generation tools do change, but the basic motions of sales and marketing haven’t changed much.

Scale 284

Scale Sales Hiring Sales Recruiting AI 284

SaaStr

JUNE 9, 2021

A ways back, I asked Brendon Cassidy, VP of Sales at LinkedIn, Adobe Sign / EchoSign, and Talkdesk to put together his playbook for double sales. … How We Increased Sales Nearly 100% In One Quarter at HackerRank – Brendon Cassidy. I thought it was a great checklist for all of us to take a look at.

Scale 284

Scale Sales Recruiting Sales Hiring Sales 284

SaaStr

JUNE 23, 2020

In SaaS, it is recruiting your VPs and management team : SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. Finding, hiring and retaining these VPs is challenge #1 for scaling up. She can be your CTO forever.

Part-Time VPE 306

Part-Time VPE CTO Hire Fractional VPE Sales Recruiting 306

SaaStr

MARCH 19, 2021

I see this all the time in marketing hires that come out of non-demand gen roles. A head of sales that doesn’t recruit at least one strong rep in the first 90 days. A VP of Sales that has never done outbound, if they don’t take it on fairly early — they never really will. “9 months.”

Sales Recruiting 349

Sales Recruiting Sales Hiring SMB Engineering 349

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.

Sales Hiring 157

Sales Hiring Sales Recruiting Sales Interviewing 157

SaaStr

NOVEMBER 16, 2021

You’ll need to hire aggressively to get to the next level and continue that rapid growth. But what roles should you hire for, and what will your org chart look like at each stage? In 2008, he founded Yammer, an enterprise software company that David grew to 500 employees and $60 million in sales. Head of Sales.

CTO Hire 284

CTO Hire Sales Hiring Sales Recruiting CTO 284

SaaStr

MARCH 1, 2024

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. She can be your CTO forever.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

SaaStr

JANUARY 25, 2021

If I had, I would have better understood the likely end point vis-a-vis freemium vs. enterprise. Not Hiring 2-3 Sales Reps to Start. I should have hired 2-3 as soon as we were ready for 1. More on that here: When You Hire Your First Sales Rep — Just Make Sure You Hire Two. I started with one.

Sales Recruiting 274

Sales Recruiting Sales Hiring Scale SaaS 274

SaaStr

JUNE 2, 2023

The company helps enterprises internationally with contextual and actionable insights to secure their cloud infrastructure. Recruit diverse leaders The goal of hiring a revenue leader is to put gasoline on finding product market fit success. Each employee hired at Wiz is individually a personal brand.

Sales Recruiting 261

Sales Recruiting Sales Hiring Scale Branding 261

SaaStr

MARCH 20, 2024

They discuss Sam’s learnings at Founders Fund, what the 2024 playbook looks like, hiring and motivating sales teams, and a handful of audience questions. On the sales side, people hired way too much. More salespeople do not equal more sales. If that’s true, then you should absolutely hire more salespeople.

Sales Hiring 300

Sales Hiring Sales Recruiting Scale Headcount 300

Sales Hacker

MAY 18, 2021

On today’s episode of Sales Hacker podcast, we have Mike Levy of TitahHouse, a transparent and effective platform, loaded with in-depth career and job intelligence, exclusively designed to connect tech-focused sales professionals with their next great position. Subscribe to the Sales Hacker Podcast. Special Announcement.

Sales Recruiting 103

Sales Recruiting Sales Hiring Data Sales 103

SaaStr

FEBRUARY 27, 2023

They credit this growth to their global team, a switch to an enterprise business model switch, and flexible work operations. Hiring a global team to achieve the vision What do you do when your company’s location limits your access to talent? You spread your hiring net and draw in as much talent as possible.

Scale 245

Scale Sales Hiring Sales Recruiting Scaling 245

SaaStr

JULY 12, 2024

Back then, remote first was a recruiting advantage. Communication is easier You can ramp people faster You can hire junior people The tradeoff is global talent. Grafana Labs still has features and capabilities they hold back that appeal to large enterprises, such as things around security and compliance. Today, not so much.

Scale 291

Scale Scaling Sales Hiring Sales Recruiting 291

SaaStr

SEPTEMBER 11, 2023

They are all avoidable : #1: Stepping Out of Sales Ok really this is mistake #1, #2, #3, #4 and #5. I see way too many founders, in the transition from founder-led sales to their first (or second) VP of Sales, look to get that time back. Instead, how they spend time in sales changes. You start hiring faster.

Sales Hiring 312

Sales Hiring Scale Sales Recruiting Scaling 312

SaaStr

JULY 11, 2023

How do you win with a high-velocity sales strategy in a fast-moving, competitive market? In a special session of Workshop Wednesday, Gorgias Founder & CEO Romain Lapeyre and Gorgias VP of Sales & Partnerships Aasif Osmany share their learnings, advice, and hacks for optimizing your sales process. Enterprise?

Sales Hiring 200

Sales Hiring SMB Sales Recruiting Payment Methods 200

SaaStr

JULY 25, 2021

They talked about product adoption, sales alignment, freemium models and lessons they have learned throughout their successful SaaS careers. As two CEO who love the art of sales and scaling, this one really was special. Recruiting is easier, but the things that don’t change are customers don’t care.

Sales Recruiting 261

Sales Recruiting Sales Hiring Scale VP of Engineering 261

SaaStr

JANUARY 9, 2020

For example, Google put a lot of work into Google Hire, its recruiting SaaS product. Salesforce is really 4+ clouds that are all at scale (sales, marketing, commerce and platform). Accelerated Enterprise Credibility. Everyone in Cloud is now dueling in the enterprise. But then shut it down. Salesforce.

Sales Recruiting 290

Sales Recruiting Scale Sales Hiring Cloud 290

SaaStr

OCTOBER 26, 2023

Co-founder and CEO at Greenhouse, Daniel Chait, sits down with SaaStr CEO and Founder Jason Lemkin to share what’s new at Greenhouse, a successful recruiting software company at $200M in ARR today. Getting off the ground is one thing — an easy pitch of being an HR tech startup focused on improving hiring.

Sales Hiring 281

Sales Hiring AI SMB Scale 281

SaaStr

SEPTEMBER 14, 2023

In this Ask Me Anything Part 1, Lemkin answers the questions: Many VCs talk about funding, yet you’re so focused on sales. Question #1: Why Are You So Focused On Sales When Other VCs Are Focused On Funding? That VP of Sales came out of Salesforce. Lemkin’s Hail Mary was hiring Brendon Cassidy when that first VP of Sales quit.

Outsourcing Services 285

Outsourcing Services Sales Hiring Scale Sales Recruiting 285

SaaStr

JANUARY 24, 2024

What should you look for in an Enterprise rep vs. a Mid-Market rep? She was hired because they saw a bit of softening in new business growth, and she came to help diagnose what was going on and help scale the business. Key Takeaways Creating Sales Acceleration at Lattice There are a few takeaways from Dini’s time at Lattice.

Scale 273

Scale Sales Hiring Scaling Revenue 273

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. It usually takes 3-4 years in the enterprise for this to happen, 1-2 in SMBs. I Don’t Have Budget.

Sales Recruiting 312

Sales Recruiting Sales Hiring Technical Review Software Review 312