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. But not usually.

Sales 126

Sales Up-sell Sell Process 126

SaaStr

JANUARY 19, 2023

So the other day Colin Cadmus, who was VP of Sales at Aircall, summarized a career question I’ve thought about many times over the past 10+ years. If you are a great AE, a great sales exec … I know you might want “more” … but is it really better to be a VP of Sales? Not zero stress.

Sales 98

Sales Promote Start-ups Closing 98

SaaStr

OCTOBER 27, 2023

Catch up on part one here , where he deep dives into what he really thinks about AI, Sales and lead Gen for SaaS in 2024. Building and scaling a startup isn’t for the faint of heart and often comes with many ups and downs that SaaS veterans have experience in. Q: When Should A Slow Growth Company Hire a Head of Sales?

Strategize 96

Strategize Growth Niche Quota 96

SaaStr

MAY 29, 2022

So we’ve talked so much over the years on SaaStr on how to hire a great VP of Sales, the difference they’ll make, and how the level-up comes quickly. Just not at your startup. And VPs of Sales do, too. A ton of great VPs of Sales have sold sales tools and similar products.

Sales 101

Sales Up-sell Drivers/motivators Gaming 101

SaaStr

JANUARY 9, 2024

The 1000+ unicorns of Covid fueled this, with ample capital to hire, hire and hire. The other day I interviewed yet another other great AE who had recently become a Director of Sales. You know you’ll have to sell yourself at this startup? Not just hire and manage people?”. Before They Hire Anymore.

Campaign 98

Campaign Up-sell Start-ups Sell 98

SaaStr

APRIL 8, 2024

Dear SaaStr: Why Do VC Backed Startups Seem To Almost Always Be Running Out of Money? But … but: A sales rep that can’t hit quota in a few months = cash drain. A VP of Marketing that can’t get you leads & opportunities = cash drain. I.e., hiring just to fill an org chart drains all the cash – fast.

Quota 77

Quota Engineering Customers Sales 77

SaaStr

MAY 8, 2024

As a SaaS veteran who built and sold a software company for nine figures, invested in startups since 2013, 10x-ing his fund, and continues to build a powerhouse community of SaaStr fans, he offers some hot takes on the communities’ burning questions. Sales is much harder than in 2021. How Does That Impact Sales and Marketing?

Quota 82

Quota GTM Price Finance 82

SaaStr

SEPTEMBER 1, 2023

Ah, hiring those first 1 or 2 sales reps. So often, they are mis-hires. But when you get that Sales Magician — they really can be a game changer. If that’s you, hiring your first few sales reps, here are our Top 10 SaaStr Posts on Hiring Your First Few Sales Reps: #1.

Quota 87

Quota Sales Gaming Closing 87

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?

Healthcare 129

Healthcare Finance Construction Government 129

SaaStr

AUGUST 8, 2023

So there’s a sort of org chart you’ll probably end up with at least twice as you start scaling in SaaS: The “Headless” Sales Org. It’s a bunch of sales reps without anyone to manage them other than … you. But if you end up not hiring a VP of Sales at that perfect moment in time (and most don’t), you’ll end up headless.

Sales 80

Sales Growth Start-ups Up-sell 80

SaaStr

DECEMBER 19, 2022

If the VP of Sales Doesn't Believe, It's All Over. So there’s a moment in time I’ve gotten pretty darn good at spotting in SaaS startups. So there’s a moment in time I’ve gotten pretty darn good at spotting in SaaS startups. That’s on you for hiring them, but it happens.

Quota 97

Quota Sales Closing Up-sell 97

Partners in Excellence

APRIL 1, 2024

He writes, “The (sales) profession is not in great shape…… This is the reason I am still in sales-I am determined to fix it! He writes, “The (sales) profession is not in great shape…… This is the reason I am still in sales-I am determined to fix it! Sales is service.

Sell 102

Sell Finance Quota Sales Experience 102

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.

Quota 60

Quota Gaming Sales Up-sell 60

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. They often melt. I say, you just gotta know the product.

Product 90

Product Objection handling Sales Up-sell 90

SaaStr

FEBRUARY 25, 2021

Ah the VP of Sales. The toughest hire. The first post is What a Great VP of Sales Actually Does. So you expect the right things, and hire your rockstar at the right time to do the right things. So you hire someone that really did it, and can do it — not a pretender. Now — who do you hire?

X-functional 145

X-functional Cross-sell Sales Up-sell 145

SaaStr

FEBRUARY 26, 2021

Brendon Cassidy, my VP of Sales wrote a version of this piece a while back. I though an updated version of this would be good for founders thinking about hiring a VP of Sales … VPs of Sales themselves … and VPs-to-be to read — Jason, ed. It isn’t going to work in a startup.

Commission 117

Commission Finance Sales Engineering 117

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. Just do it!

Quota 145

Quota B2C Sales Closing 145

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. We were coming off an environment where startup funding was as fruitful as ever. On the sales side, people hired way too much. Each VC has a different “flavor.”

Quota 101

Quota Finance Drivers/motivators GTM 101

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.

Quota 144

Quota Sales Promote Up-sell 144

SaaStr

JANUARY 16, 2023

Most salespeople will succeed somewhere … but fail at >your< specific startup. Earlier stage startups: – Have no brand – Have no/little training – Have very few resources. Most important is making sure they will thrive at your startup. The ones you hire before your first great VP of Sales.

Up-sell 104

Up-sell Sales Support Price Start-ups 104

SaaStr

DECEMBER 24, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: 10+ Signs of a Mediocre Hire The Where, When, and How of AI with Theory Ventures, Open AI and More 15 Signs You Have a SaaS Metrics Problem (and How to Fix it) 4 Recent, Very Bad, Truly Terrible Customer Success Experiences.

Pitch 83

Pitch Product Customers Sales 83

SaaStr

JULY 17, 2022

Q: Dear SaaStr: When Should a Startup Hire its First Sales Person, and What Should Their Profile Look Like? Try to close at least 10–20 customers yourself first, before you hire a sales rep. Then, hire a sales rep to help you. Hire someone that has sold at your price point / deal size.

A/B testing 85

A/B testing Quota Closing Sales 85

SaaStr

MAY 12, 2022

The biggest mistake you can make as a founder when you hire your first VP of Sales is stepping out of sales. It only works with the very best VPs of Sales. Every other first VP of Sales needs you doing at least half of what you were doing before. A founder hires a Pretty Good First VP of Sales.

Contract 95

Contract Sales Engineering Prospecting 95

SaaStr

JANUARY 29, 2023

Basically all of the SaaS CEOs/founders I know of have made at least one terrible VP+ level hire. Sometimes it’s VP Sales (OK, often, this is the most common mishire — another post here on what a really great VPS can do for you, and how a poor one can wreck your company, coming).

Start-ups 111

Start-ups Up-sell Meeting Closing 111

SaaStr

OCTOBER 1, 2022

So That VP That Has Done it Before always cost more than the stretch VP. Recently I talked with a founder who had hired a seasoned VP of Marketing at $3m that had an 8 person content marketing team. VPs of Marketing, Success, Product, Sales and more that really have done it. As they should. Not really.

Quota 115

Quota Campaign Customers Process 115

SaaStr

DECEMBER 26, 2023

Dear SaaStr: What Is A Good Demo Conversion Rate for a SaaS Startup? If fewer than 8%-10% or so of your demos convert to paid customers, you’ll start to burn out your sales team. This is why SaaS start-ups often are so proud of their “amazing” conversion rates before they hire a real VP of Demand Gen. Even that’s a lot.

Conversion 92

Conversion Quota Engineering Start-ups 92

SaaStr

MARCH 5, 2023

Ode to the $100,000,000 Exit Dear SaaStr: Should You Hire Someone That Seems Good … But Always Job Hops? SaaStr 639: Scaling a SaaS Sales Team While Building Culture with Figma VP of Sales Scott Pugh   3. SaaStr 639: Scaling a SaaS Sales Team While Building Culture with Figma VP of Sales Scott Pugh   3.

Growth 79

Growth Sales Customers Product 79

SaaStr

JULY 12, 2021

Q: What are some common blind spots and mistakes startups make when hiring for and building out a sales team? Some of the top blind spots founders and even VPs of Sales make: #1. You hire a sales rep to sell before you can prove you can do it yourself. Otherwise, they don’t know sales.

Quota 106

Quota Sales Up-sell Closing 106

SaaStr

JUNE 4, 2023

But I’m still going to make one simple suggestion when you go to hire your first set of VPs, your second, or even your third: Beware The Mediocre Recycled What does that mean? Well, there is a certain type of VP candidate that worked somewhere good once, twice, sometimes even three times. A VP of Sales role.

Follow-up 93

Follow-up Customers Product Sales 93

SaaStr

SEPTEMBER 21, 2020

So much of sales is process and execution. When you are finally ready to hire your VP of Sales, oftentimes, there’s often a bit of a quiet panic around time. About getting the hire done. You can’t hire more reps yourself. Why would a great VP of Sales join a start-up with mediocre growth?

Growth 102

Growth Sales Start-ups Process 102

SaaStr

SEPTEMBER 17, 2023

As a sales exec, you may not know actually the product well. A few recent examples: Example #1: I was recently chatting with a VP of Sales about a job position, which I get he wasn’t 100% sure he wanted. But he took 4 days to get back to the startup on it. Don’t hire that one. Or to get a demo?

Contact 98

Contact Sales Prospecting Customers 98

SaaStr

JULY 26, 2021

Q: Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or whatever) customers. Then, hire first 2 reps. Ideally, hire your Head of Demand Gen around now.

A/B testing 107

A/B testing Quota Engineering Sales 107

SaaStr

SEPTEMBER 28, 2022

Dear SaaStr: What do you look for when hiring a VP of Product for a B2B SaaS? In particular, the dilemma I’m facing is hiring between a SaaS expert or a target market expert. First, I’d go for a SaaS expert over a domain/target market expert in just about any senior hire — VP Product, VP Sales, VP Marketing.

Product 103

Product B2C B2B Engineering 103

SaaStr

JANUARY 4, 2023

It may seem counterintuitive to seek out a sales leadership hire during this time of slowed hiring, but it’s the number one topic that many founders talk about and many SDRs, AEs, and sales managers ask about. . Founders may ask, “how do I find the right sales leadership hire?” But that’s not good enough. .

Networking 76

Networking Promote Growth Start-ups 76

SaaStr

SEPTEMBER 12, 2023

You Have to Train Sales Reps 3–10. You have to start formal sales training by rep #3. Hire Early. Hire your first customer success manager as early as you can afford to once you have some larger customers. How would you structure a sales team to get you from $10s to $100 millions in revenue? Or they fail.

Price 91

Price Contract Territory Growth 91

SaaStr

APRIL 12, 2021

The biggest mistake folks make when they go to hire a VP of Sales is hiring a top AE that's never really built a team. But it does not remotely prepare you to be a VP of Sales on its own. Not until you are Uipath, or Canva, or Algolia, or whatever the next super hot startup is.

Inside sales 128

Inside sales Start-ups Strategize Growth 128

SaaStr

OCTOBER 1, 2022

What almost never works, somewhat surprisingly, is hiring a Director of Outbound as your first outbound hire. I see many startups want to add outbound, but not really have a lot of experience. And especially, a new VP of Sales comes in without real outbound experience. Why does this seemingly logical hire fail?

Niche 97

Niche Pipeline Gaming Start-ups 97