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.

Sales Recruiting 165

Sales Recruiting Sales Hiring Sales Leadership 165

SaaStr

JANUARY 27, 2023

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. Great Companies Attract Great Talent Blond and Braverman have enjoyed successful careers as sales leaders in high-performing companies.

Sales Recruiting 244

Sales Recruiting Sales Hiring Scale Compensation 244

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.

Sales Recruiting 246

Sales Recruiting Product Marketing Scale Sales Hiring 246

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 195

Sales Recruiting Sales Hiring Scale Underperforming Technical Team 195

SaaStr

DECEMBER 9, 2023

Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. It is incredibly hard to figure out how to replicate the magic of the first 1 or 2 sales reps that work closely with the CEO.

Sales Recruiting 290

Sales Recruiting Sales Hiring Sales Management 290

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. you might ask.

Sales Recruiting 363

Sales Recruiting Sales Hiring Scale Sales 363

SaaStr

DECEMBER 16, 2020

We’ve talked a lot on SaaStr about how to make that critical hire: the VP Sales. 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. And lessons learned on what a VP Sales really does. Job #1 is Recruiting. It all clicks.

Sales Recruiting 360

Sales Recruiting Sales Hiring Sales Engineering 360

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. I wanted to take a moment to explore the flip-side … a guide to why first-time VPs of Sales that finally get their shot — fail.

Sales Hiring 359

Sales Hiring Sales Recruiting Sales Headcount 359

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. You want the sales ops help scaled up and helping before then.

Sales Hiring 296

Sales Hiring Sales Recruiting Scale Sales 296

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.

Sales Recruiting 325

Sales Recruiting Scale Venture Capital Sales Hiring 325

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. In fact, the best sales leaders always upgrade the team within 60 days of taking a new role.

Sales Recruiting 299

Sales Recruiting Sales Hiring Scale Sales 299

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.

Sales Recruiting 317

Sales Recruiting Sales Hiring Sales Interviewing 317

SaaStr

JULY 11, 2020

When I catch up with founders on the march from $1m to $10m in ARR, the number one topic has always shifted to recruiting. Where do i find a great VP of Sales, Marketing, Engineering, Product, Customer Success, etc.? Some times, it seems like simply building a management team is all you have time for. But it’s not.

Sales Recruiting 363

Sales Recruiting Management Engineering Customer Success 363

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. I was a local sales manager or regional manager.

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

SaaStr

JANUARY 24, 2021

2021 will be the year SaaS sales evolves the most since the Appexchange ecosystem started to take off ~15 years ago, which spawned the entire notion of a true sales app stack. The permanent move to distributed sales teams. Almost every SaaS VP of Sales and CRO I’ve talked to in the past few months isn’t going back.

Sales Recruiting 354

Sales Recruiting Scale Technical Review Sales 354

SaaStr

NOVEMBER 19, 2020

More on that here and a great video discussion below: You’ll probably be ready for your first VP of Sales by $1m in ARR. We’ve talked about this a lot on SaaStr, but hiring a true VP of Sales before you have 2 reps hitting quota (and thus a repeatable, if not yet fully repeating process) is too early. Earlier is better.

Part-Time VPE 363

Part-Time VPE Sales Hiring CTO Hire Scale 363

SaaStr

APRIL 29, 2019

Either by yourself, or with a Sales Ops / Marketing Ops / Some Sort of Ops leader under you. Look for dashboards, strong project management, strong pipeline projection after $5m ARR. If you don’t see things getting more organized, that manager can’t scale. Inability to hire great Directors / managers under them.

Sales Recruiting 278

Sales Recruiting Sales Hiring Scale Management 278

Tom Tunguz

SEPTEMBER 7, 2020

Whether you manage a team of engineers, a team of regional sales managers, or the company, your first responsibility is to hire and successfully manage the seven people who will form your leadership team. First, as a company grows, the most important thing is recruiting.

Sales Hiring 263

Sales Hiring Sales Recruiting Management Leadership 263

SaaStr

SEPTEMBER 10, 2020

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. Don’t just check who they managed at their last company. Not inherited as a manager. And you end up with hires that can’t recruit great people.

Part-Time VPE 352

Part-Time VPE Sales Hiring CTO Hire Sales Recruiting 352

SaaStr

JANUARY 3, 2024

Dear SaaStr: Should I Go Into SaaS Sales? If you aren’t sure you want to go into sales — don’t do it. Maybe in 2021, when many SaaS leaders were growing at simply unprecedented rates, could succeed in sales if you weren’t sure you wanted to sell. link] You will build amazing people, management and recruiting skills.

Sales Recruiting 298

Sales Recruiting Sales SaaS Management 298

The Daily Egg

MAY 13, 2021

Getting your sales job advertisement in front of eyeballs can be an uphill task but doable with targeted keywords. Most managers and recruiters will admit to having a hard time crafting appealing job postings. The post Sales Job Descriptions and Titles – The Complete Guide appeared first on The Daily Egg.

Sales Recruiting 283

Sales Recruiting Sales Advertising Management 283

SaaStr

MAY 17, 2021

Q: Dear SaaStr: What is the path to become a great VP of Sales? Each story is different, but there is one clear penultimate step: recruiting and managing a small team yourself. What 95 times out of 100 is a recipe for failure is jumping straight from successful individual rep to VP of sales. Not just managing one.

Sales Recruiting 243

Sales Recruiting Sales Hiring Sales Startup 243

SaaStr

FEBRUARY 25, 2021

Ah the VP of Sales. The first post is What a Great VP of Sales Actually Does. The second post is a script for you to use (and modify as you see fit) – 10 Great Questions to Ask a VP Sales Candidate. Just so you know, there are 48 Different Types of VP Sales. The toughest hire. Such a high failure rate.

Sales Hiring 364

Sales Hiring Scale Sales Recruiting Sales 364

Tom Tunguz

APRIL 5, 2020

If we tally the reductions by category, travel, retail, fitness, real estate, transportation, and recruiting constitute the top 6 categories. Aside from recruiting, these are all consumer discretionary spend categories. ClassPass, one of the fitness startups to reduce headcount, reported a 95% drop in sales in 10 days.

Sales Recruiting 357

Sales Recruiting Startup Headcount Sales Hiring 357

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. Ask who they are.

Sales Recruiting 334

Sales Recruiting Sales Hiring Scale Sales 334

TechEmpower SaaS

MARCH 4, 2024

Key Functions with High Impact Generative AI is revolutionizing sales by enabling dynamic pricing and personalized customer interactions, boosting conversion rates and customer satisfaction. Post-sale, AI analyzes customer data to improve service and loyalty, making it a cornerstone of modern sales methodologies.

Generative AI 443

Generative AI AI CTO Hire Sales Recruiting 443

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. Way too many folks give managers a pass here that never understand the product. Sales is hard.

Sales Hiring 308

Sales Hiring Sales Recruiting Sales Interviewing 308

SaaStr

JANUARY 30, 2021

Most of us can’t afford to hire a VPM 12 months before we have our first customer, and we can’t survive through 10 sales reps without one. It’s not quite as terrible as waiting too long for a VP of Sales. A great VP of Marketing can help make the sales reps better qualitatively, even before you have a VP of Sales.

Sales Hiring 352

Sales Hiring Sales Recruiting Scale Marketing 352

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

JUNE 22, 2021

The other day I saw a VP of Sales flame out and resign with no notice from a SaaS company doing $10m ARR growing quickly. So I thought it might be helpful to brush off the topic of alignment between Sales and Marketing by updating a classic post on the topic. The original version here on Lattice Engines’ Sales and Marketing Hub.

Sales Recruiting 317

Sales Recruiting Scale Sales Hiring Revenue 317

SaaStr

DECEMBER 13, 2021

Either by yourself, or with a Sales Ops / Marketing Ops / Some Sort of Ops leader under you. Look for dashboards, strong project management, strong pipeline projection after $5m ARR. If you don’t see things getting more organized, that manager can’t scale. Inability to hire great Directors / managers under them.

Scale 354

Scale Sales Recruiting Sales Hiring Scaling 354

SaaStr

AUGUST 12, 2021

Q: What are the top 3 biggest concerns in managing a first sales team? A few of the top ones: Recruiting. Top sales people want to work for a great VP of Sales. If you don’t have one, it’s very hard to attract top sales reps. All sales execs want to make a lot of money :). Paying the best ones well.

Sales Recruiting 290

Sales Recruiting Sales Hiring Sales Onboarding 290

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 264

Sales Recruiting Sales Hiring Sales SMB 264

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? Month 24: closes 50% of top enterprise accounts.

Sales Hiring 306

Sales Hiring Sales Recruiting SMB Sales 306

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 316

Sales Hiring Sales Recruiting Scale Outbound Sales Team 316

SaaStr

MARCH 18, 2025

Rather than seeing this as a liability, Wiz leveraged it as a strategic advantage — even in its sales team. By building operational capacity ahead of revenue, they avoided the common trap of having sales capabilities outstrip the organization’s ability to deliver and support those sales.

Scale 191

Scale Sales Hiring Scaling Headcount 191

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.

Sales Hiring 363

Sales Hiring Scale Sales Recruiting Sales 363