SaaStr

AUGUST 28, 2020

I know we’ve hit a number of these points individually before on SaaStr, but after getting asked about the top mistakes hiring your first sales team so many times over the years, I thought it would be worthwhile to assemble a Top 10 List. Make fewer of them and you’ll scale faster with less stress. It’s sales, after all.

Sales Hiring 332

Sales Hiring Sales Recruiting Scale Sales 332

SaaStr

SEPTEMBER 13, 2020

Recruiting is tough. But to be a great CEO, you need to find a way to force yourself to be a great recruiter. Let me share some learnings, and what I do now to force myself to be a better recruiter. First, you will budget a ton of time for recruiting. Hire external recruiters — and be very good to them.

Sales Recruiting 363

Sales Recruiting Sales Hiring Interviewing Scale 363

SaaStr

SEPTEMBER 10, 2020

Perhaps the single most important thing you can ever do in SaaS, at least after $1m in ARR or so, is hire the best VPs you can. We’ve talked a lot over the years about how not to hire a wrong VP of Sales — 70%+ of the first VPs of Sales don’t make it even 10 months. You need to hire up-and-comers.

Part-Time VPE 352

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 352

SaaStr

MARCH 18, 2025

It’s an incredible look back on scaling and more: Colin Jones, first Chief Revenue Officer at Wiz. 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

SaaStr

SEPTEMBER 27, 2021

In the “old” days, there was a rough rule that as soon as you are bringing on more than 1–2 reps a quarter, you needed to hire a director of sales ops. That at that point, at a minimum, there would be too much administrative work for your VP of Sales to handle it herself. One manager can only really manage 8 AEs.

Sales Hiring 290

Sales Hiring Sales Recruiting Scale Sales 290

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.

Sales Hiring 304

Sales Hiring Sales Recruiting Scale Technical Review 304

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.

Sales Recruiting 184

Sales Recruiting Sales Hiring Scale Interviewing 184

Tom Tunguz

SEPTEMBER 8, 2022

This chart holds the secret to successful hiring of go-to-market teams. A stack rank of attributes within HubSpot account executive candidates that correlate to quota attainment. The pushier the account executive, the worse the result. I think it’s still one of the best books on how to repeatably scale sales teams.

Sales Hiring 349

Sales Hiring Sales Recruiting Scale Marketing 349

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. Define your hiring profile.

Scale 273

Scale Sales Recruiting Sales Hiring Scaling 273

SaaStr

DECEMBER 13, 2021

It’s a bit of a bummer than oftentimes, once you finally hire a few great VPs at $1m, $2m, $3m ARR … and they do a great job … that they then don’t scale. A few signs I see again and again of VPs that can’t scale beyond $5m-$10m ARR: Lack of organization. But it doesn’t scale. They get it.

Scale 354

Scale Sales Recruiting Sales Hiring Scaling 354

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. In the early days, Revenue Per Lead is critical.

Sales Hiring 352

Sales Hiring Sales Recruiting Scale Marketing 352

SaaStr

MARCH 5, 2025

Codium is one of the fastest-growing startups in the AI coding assistant space, having scaled its go-to-market team from 3 to 75 in just under a year. Before hiring their first sales reps, the founders personally closed millions in revenue. Their strategy?

Sales Hiring 180

Sales Hiring Scale Sales Recruiting AI 180

SaaStr

JULY 13, 2023

A strong sales leader is vital to any company hoping to scale. With this in mind, hiring for the Head of Sales role is one of the most important things a business can do. Fortunately, there are ways to avoid common hiring mistakes. Fortunately, there are ways to avoid common hiring mistakes.

Sales Recruiting 244

Sales Recruiting Sales Hiring Scale Sales 244

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. And your first VP of Marketing just increases qualified leads by 25%.

Part-Time VPE 363

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 363

SaaStr

AUGUST 14, 2020

A mistake many founders make is hiring a VP of Sales who has many strengths — but not at sales per se. A VP of Sales who is smart, polished, and worked at the right place, in a management-level position. That can talk about quota attainment and sales operations and scaling and number.

Sales Recruiting 363

Sales Recruiting Sales Hiring Scale Sales 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.

Sales Recruiting 244

Sales Recruiting Sales Hiring Scale Compensation 244

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.

Sales Recruiting 265

Sales Recruiting Sales Hiring Scale Engineering 265

SaaStr

MARCH 12, 2021

We’ve talked a lot about hiring a great VP of Sales at SaaStr, and I’ve relinked to some of the most popular posts below. But after 5+ years of SaaStr.com, I think we can almost boil it all down to 2 things to look for when you make the hire — and 2 things not to look for as much. That takes years to learn.

Sales Hiring 274

Sales Hiring Sales Recruiting Scale Development Team Review 274

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

MAY 31, 2025

Key hires like a VP of Engineering or VP of Product might get 1%-2% each. Another way to think of this stage; the first 10 or so should probably get at least twice the equity of others for joining early, if they are mission-critical hires. This ensures you have enough to reward early hires without running out too quickly.

Part-Time VPE 202

Part-Time VPE Sales Hiring Sales Recruiting Compensation 202

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. Maybe you can wait longer, sometimes a lot longer. — Jason ?BeKind?

Sales Hiring 326

Sales Hiring Sales Recruiting Scale Sales 326

SaaStr

DECEMBER 16, 2020

Q: What makes a great sales leader? The best sales managers / directors / VPs: Recruit great team members. Sales requires a linear number of hires to grow bookings. So you have to be a great recruiter to scale. Retain the top hires. But the best sales leaders know where they are #1.

Sales Recruiting 293

Sales Recruiting Sales Hiring Scale Sales 293

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 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. For better or worse, there’s a perception that Bay Area startups are more ambitious and better positioned to scale globally. This is minor but still a plus. #5.

Sales Recruiting 224

Sales Recruiting Scale Sales Hiring B2B 224

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.

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

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. So I’d hire earlier here rather than wait.

Sales Hiring 284

Sales Hiring Part-Time VPE Scale Sales Recruiting 284

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.

Sales Hiring 349

Sales Hiring Sales Recruiting Scale Scaling 349

SaaStr

JUNE 20, 2025

The Billion-Dollar AI Unicorn Factory The scale of AI startup funding isn’t just impressive — it’s existential for SaaS: The AI Billion-Dollar Club: OpenAI : $8.4 billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3 billion in funding xAI : $6.4

AI Search 289

AI Search Artificial Intelligence AI CTO Hire 289

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.

Sales Hiring 311

Sales Hiring Sales Recruiting Scale Outbound Sales Team 311

SaaStr

JUNE 14, 2020

The lead commit goes up each quarter and every year. To hire 3-4 folks to do what you used to do mostly yourself. To want a head of sales operations and a director of sales to help carry the load not later … but on Day 1. You can’t scale after that without one. In many cases this is a good thing.

Sales Hiring 299

Sales Hiring Scale Sales Recruiting SaaS 299

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.

Sales Recruiting 290

Sales Recruiting Sales Hiring Scale Outsourced Development 290

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.

Sales Recruiting 246

Sales Recruiting Sales Hiring Scale Enterprise 246

SaaStr

JULY 12, 2024

Scaling to $150M ARR and beyond is no simple task. Back then, remote first was a recruiting advantage. Will this change as Grafana Labs scales? Communication is easier You can ramp people faster You can hire junior people The tradeoff is global talent. First, let’s rewind the clock and look at Grafana Labs’ origin story.

Scale 291

Scale Scaling Sales Hiring Sales Recruiting 291

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.

Sales Recruiting 246

Sales Recruiting Product Marketing Scale Sales Hiring 246

SaaStr

MARCH 1, 2024

Dear SaaStr: What’s The Number One Challenge for Scale-Up Stage Founders? 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 will need a VP of Product to scale your roadmap.

Scale 274

Scale Part-Time VPE CTO Hire Fractional VPE 274

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 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. Here are some things to remember when you think about scaling your next big SaaS company.

Sales Recruiting 251

Sales Recruiting Sales Hiring Scale Sales 251