SaaStr

APRIL 21, 2022

Yes, sometimes it’s OK to hire a VP of Sales that everyone loves. At least 9 times out of 10, if everyone on the team loves a VP of Sales, it’s the wrong hire. And this especially matters because I often see CEOs picking between 2 final VP of Sales candidates. VCs love VP of Sales that sell up well.

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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. That result alone should encourage rethinking of AE interviewing. What is it?

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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

MARCH 15, 2025

It’s live on SaaStr.com itself and you can also access it here and talk to AI Jason about any of 1000s and 1000s of B2B, sales, SaaS, VC, etc. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days. Here are some of the top ones: “How My VP, Sales Doubled Our Sales in 90 Days.

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SaaStr

MARCH 23, 2025

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. Create Compelling Economic Incentives For sales talent, compensation is critical.

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SaaStr

JANUARY 6, 2021

Finding the perfect VP of Sales position can be daunting, especially in the middle of a global pandemic. Candidates need to find opportunities that not only fit their sales experience and stretch goals, but also companies that are coming out of the pandemic with momentum. Who is looking to hire a VP of Sales in January / Q1?

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SaaStr

MAY 9, 2021

The toughest hire of all is probably your VP of Sales. What are the right interview questions? When is too early to make the hire? When do you know that you’ve made a mis-hire? How far can you stretch to make the hire? What’s fair to expect from a VP of Sales, and what isn’t?

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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

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

JUNE 25, 2020

One of the classic original SaaStr posts was on the Top 10 Questions to Ask a VP of Sales Candidate. We did an update of that classic post below together with this brand new video on the topic: Use this script for hiring that first VP of Sales. Ready to hire your first VP Sales? And When to Hire One.

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SaaStr

MARCH 11, 2024

So you’re hiring your first few sales reps in the early days? Before you have a great VP of Sales? So you need a very certain type of sales rep. They’re Late Many will challenge me here, but if they’re late to the interview, they’ll be late to customer calls, too. That’s fine.

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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

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

OCTOBER 7, 2020

As you scale up in SaaS, one thing I can almost guarantee is that you are going to hire some VPs who were either fired or quit their last role. So you’ll end up hiring VPs who went through a significant transition at their last gig, sometimes an involuntary one. They are good managers, and they know there is no upside here.

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SaaStr

MAY 10, 2024

At this week’s Workshop Wednesday, Lucas Price, former SVP of Sales at Zipwhip and founder and CEO at Yardstick, shares his insights on how to hire and build a high-performing sales team. During that time, he wasted a lot of money on failed sales hires and decided to learn everything about hiring sellers.

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SaaStr

OCTOBER 2, 2024

Dear SaaStr: Why Do Founders Hire So Many Terrible VPs that Mislead Them? And Hiring folks to do something you don’t know yourself and/or haven’t done yourself. If you hire a VP of Sales and have never done sales yourself, you won’t really know. And have them interview the top 1-2 candidates for each role.

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SaaStr

AUGUST 31, 2023

Dear SaaStr: How does a First Time Founder Identify 10x Hires? How do you hire a great CTO, a great VP of Product, a great VP of Sales … if you’ve never worked with one? There’s a reason almost every founder you talk to had a mis-hire for their first head of sales. It’s hard.

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SaaStr

AUGUST 4, 2021

Ask them what those top 3 are before you hire them. I’ve interviewed 100s of VP of marketing candidates over the past years and I can tell you one think — it’s easy to spot the ones that won’t work out. How have you worked with the sales team in the past? Were they close to the VP of Sales?

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SaaStr

JULY 12, 2022

One of the first what How to Hire a Great VP of Sales at the New York Enterprise Tech Meet-Up (thank you to John Lehr and Work-Bench for setting this up). The Number One Thing You Can Do to Accelerate Your Business Post-Initial Traction is Hiring a Great VP of Sales. I don’t know anything about sales.

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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

SEPTEMBER 24, 2020

That when you make a mis-hire, you'll always look back and say you should have made a change 3-4 month earlier? When to hire them. How to interview them and qualify them. Some classics here: How My VP, Sales Doubled Our Sales in 90 Days. If Your VP Sales Isn’t Going to Work Out — You’ll Know in 30 Days.

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SaaStr

JANUARY 26, 2021

There’s nothing wrong with hiring folks from the competition. Only hire them if you still would if they worked somewhere else. The time will come when you are first tempted to hire someone from your competitor. Hiring from your Competitor. Interview them, learn from them … but generally, stop there.

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SaaStr

FEBRUARY 26, 2024

We all saw the Cloudflare sales rep on social media not work out. It reminded me of a golden rule it took me years and years to figure out: If a new hire doesn’t work out, it’s always 100% your fault What do I mean? Did the hire really meet the bar? Did you test the hire for real before they started?

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SaaStr

JULY 11, 2024

How Do You Sift Out the Bitter and Broken Individuals When Hiring? As a startup, most people who come to an interview appear happy. You interview 30 people. If it’s a role you’ve never hired, find someone great at it and have them do your final interview. What do the best Heads of Product and VPs of Sales say?

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SaaStr

FEBRUARY 1, 2025

When I look at the VP of Sales / CRO that didnt work out the past 12-18 months across the SaaStr Fund portfolio and my ecosystem, one thing stands out. And its an old SaaStr theme: #1: You have to hire folks in sales where their last job was harder. There may exceptions at rocketships. You often fly. Voice APIs?

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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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Tom Tunguz

FEBRUARY 3, 2020

Market challenger sales are very different. In fact, this is where the name challenger sale originates. Sales cycles lengthen, demand more work, and consumer more time. When you interview salespeople for your startup, do you consider their experience at a market leader or market challenger? How do you sell a new product?

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SaaStr

JULY 18, 2022

Q: Dear SaaStr: What Are Some Good Strategies To Hire People In The Early Days? A few basic thoughts … that many still don’t get right: Don’t hire anyone that doesn’t understand their functional area better than you do. Don’t hire anyone you don’t believe in. If you’re not sure how to hire for a role, get an advisor that does.

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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? Probably, even slower.

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SaaStr

JUNE 5, 2022

Most of you are hiring twice as many sales reps as last year. This isn’t an epic insight, but I did the poll because I find so many SaaS founders underestimate how many reps you have to hire. If you want to double, you have to at least double your sales team. At least. #23. Of course not. #24. Another Sigh.

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SaaStr

JUNE 27, 2020

A little while back we put together some of the top sales & marketing mistakes SaaS companies and founders make, especially in the early days. Sales: Hiring any reps you wouldn’t buy from yourself. Later, once you have a strong VP of Sales, it’s fine though. Your sales reps need to eat. Hiring just 1 rep.

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SaaStr

JULY 14, 2024

Hiring and Interviewing Tips: Jason emphasizes the importance of interviewing at least 30 candidates for a role and consulting with an expert in the field to interview the final candidate. He highlights that many companies, like Canva and Asana, start with PLG but eventually incorporate a sales-led motion as they scale.

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SaaStr

AUGUST 19, 2022

So we’ve talked a lot of the years on SaaStr on how to avoid a mis-hire for a key VP role: We’ve talked here about the 48 Types of VPs of Sales, and making sure you hire the right type. We’ve talked here about how to hire the right VP of Marketing, so you get leads and not just blue pens with your logo on them.

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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

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

SEPTEMBER 13, 2020

And what I wish I’d done better as a SaaS CEO: Force yourself to interview 30 candidates for each VP position. You’ll have to, to get through 30 interviews. Second, you’ll force yourself to spend more time tracking and managing candidates. Hire external recruiters — and be very good to them. But plan on 30.

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SaaStr

FEBRUARY 2, 2023

Product marketing can be difficult, and managing product launches and rollouts can be complex. Your sales rise to a very high level You may realize that your sales are reaching high levels, but at the same time, you may encounter a situation where there needs to be more structure or control in your sales process.

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