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

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 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

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

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. Don’t.

Sales Hiring 352

Sales Hiring Sales Recruiting Scale Marketing 352

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].

Part-Time VPE 363

Part-Time VPE Sales Hiring CTO Hire Scale 363

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 198

Part-Time VPE Sales Hiring Sales Recruiting Compensation 198

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

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

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 222

Sales Recruiting Scale Sales Hiring B2B 222

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 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

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 179

Scale Sales Hiring Scaling Headcount 179

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

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 195

Sales Recruiting Interviewing Sales Hiring Scale 195

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

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 179

Sales Hiring Scale Sales Recruiting AI 179

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

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

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

OCTOBER 27, 2022

You need engineering, product in all start-ups — but in SaaS, even in the very early days, you also need sales, client success, true support, demand gen marketing, etc. 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 293

Sales Hiring Sales Recruiting Scale Scaling 293

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 330

Sales Recruiting Sales Hiring Scale Sales 330

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

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

JUNE 14, 2020

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. To not have to manage any customers yourself in customer success, and instead be a strategist. You can’t scale after that without one.

Sales Hiring 297

Sales Hiring Scale Sales Recruiting SaaS 297

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. Hi everyone.

Sales Hiring 261

Sales Hiring Sales Recruiting Scale Sales 261

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

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 188

Sales Recruiting Sales Hiring Scale Underperforming Technical Team 188

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

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

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 14, 2022

We’ve talked a ton about How to Hire a Great VP of Sales on SaaStr, but I wanted to highlight a few VP of Sales “personas” that I rarely, if ever, see work out. Because again and again, many of your will hire this VP of Sales. Here are the types of VP of Sales that just never work out.

Sales Recruiting 300

Sales Recruiting Sales Hiring Technical Review Scale 300

SaaStr

SEPTEMBER 8, 2024

So just as supply chain logistics juggernaut Flexport was beginning to scale, founder CEO Ryan Petersen came to SaaStr Annual to share his top lessons — and mistakes. When building a list, try to define your potential customer as granularly as possible – size, location, industry, ideal buyer, sales process, technology stack, etc.

Sales Recruiting 322

Sales Recruiting Scale Venture Capital Sales Hiring 322

SaaStr

JULY 2, 2021

I’ve written a lot about this, but for most start-ups, you can boil it down to two criteria any first VP of Sales just has to meet: Has she built at least a small team before? Have they hired at least 2–3 reps that have performed well? If you can hire 2–3 great ones, you can likely scale and hire 20–30.

Sales Recruiting 284

Sales Recruiting Sales Hiring Scale Development Team Review 284

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