SaaStr

NOVEMBER 20, 2023

Dear SaaStr: What is The Best Way to Hire Your First Sales Rep? For at least your first few reps: hire someone >>you<< would buy >>your product<< from. I.e., Do not hire someone just because they worked at Facebook or Salesforce or even Datadog or Shopify in “sales”.

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SaaStr

OCTOBER 16, 2023

We’re hiring at SaaStr!! Take over our complex email campaigns to drive event attendance and ticket sales, as well as our 4 weekly newsletters. Senior Sales Executive. Own 50+ accounts. The post We’re Hiring at SaaStr! We’ve got at least 6 roles open: Director of Email / Growth Marketing.

Sales Hiring 282

Sales Hiring Healthcare Growth Marketing Sales 282

SaaStr

NOVEMBER 4, 2024

So recently we did a deep dive with Henry Schuck, founder CEO of ZoomInfo, on AI in Sales and so much more. But make sure if nothing else, you hire One Senior Exec a Quarter. I need a VP of Growth, and a VP of Sales, and to fix product, and to … So much to fix. And they end up hiring no one great for months and quarters on end.

Sales Hiring 242

Sales Hiring Sales Recruiting Interviewing Finance 242

SaaStr

DECEMBER 19, 2023

Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? For a higher-velocity, in-bound driven SaaS product, most sales reps will have trouble processing more than 50 or so truly qualified leads a month. Before $10m ARR or so, more qualified leads = more sales.

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Sales Hiring Scale Scaling Sales 282

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. Don’t make the hire. If they just show up at 2:05 onto the Zoom though, don’t make the hire. #2. Not during founder-led sales.

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Sales Hiring Sales Interviewing compliance 244

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

SEPTEMBER 5, 2024

And the mistake they make is they finally hire a great VP of Sales, Marketing, CS, Product, etc. that they really believe in … and then … they sort of veto or don’t quite believe in their first hire. Or “Jameson would be my first hire”. Don’t make the hire. Go hire whomever you want as your right hand.

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Sales Hiring Sales Marketing 289

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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Sales Hiring Social Media Interviewing Education 266

SaaStr

SEPTEMBER 21, 2023

But we’re lapping tougher times for many, and for many others, it’s just plain time to hire again. So many Cloud and SaaS leaders kept hiring flat for the past 12-18 months, and yet still grew. That works for a while, but you end up with not enough headcount if you do freeze hiring but still want to grow.

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Sales Hiring Headcount Scale Cloud 296

SaaStr

APRIL 1, 2023

On the hiring side, it often seemed like you just couldn’t hire anyone. Everyone was hiring everyone, anyone, back in mid-2021. We hired job hoppers that never stayed anywhere for more than 18 months for leadership roles. The post Lowering the Hiring (And Investing) Bar Didn’t Work appeared first on SaaStr.

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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. I think it’s a combination of three factors: Trusting your team.

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Sales Hiring Scale Interviewing Engineering 255

SaaStr

NOVEMBER 14, 2024

So Salesforce is hiring 1,000 more salespeople to sell AI software … that is supposed to reduce the need for humans and replace them with agents pic.twitter.com/hsjlrz3mqS — Jason ✨????SaaStr If it’s the latter, maybe AI will just create even more enterprise sales jobs. Maybe it’s not that clear. Or a human?

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Sales Hiring Sales AI Enterprise 252

SaaStr

NOVEMBER 30, 2024

Here’s an uncomfortable truth about SaaS companies: the majority of first-time VPs of Sales don’t make it past 12 months. As someone who has both succeeded and failed at making this critical hire, I can tell you that when it works, it’s transformative. When it doesn’t, it’s potentially catastrophic.

Sales Hiring 282

Sales Hiring Sales Recruiting Sales Headcount 282

SaaStr

SEPTEMBER 19, 2024

There are 3 types of hires you may be tempted to make now, but you just can’t: The Jaded, The Broken, and The Done They’ve always existed, it’s just there are so many more folks with great LinkedIns and experiences in these categories in SaaS. Just don’t hire them. You can’t hire them. Hints of it.

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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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Sales Hiring Sales Recruiting Sales Interviewing 243

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.

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Sales Hiring Scale Sales Startup 231

SaaStr

OCTOBER 11, 2024

ARR and is looking to hire an experienced COO how much equity should they give him/her? You should find, hire, and manage the VPs of Sales, Marketing, Customer Success, Product and Engineering and even Finance yourself. ARR is Hiring a COO, How Much Equity Should They Get? Dear SaaStr: If a startup is at $1.5M

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Sales Hiring Startup Finance Engineering 250

SaaStr

DECEMBER 7, 2023

Dear SaaStr: When Should I Expect New Sales Hires to Be On Target? sales cycles. You should know well before that if you are managing her or him — you’ll usually know by half a sales cycle. More here: Dear SaaStr: How Long Should You Give a New Sales Rep? At least by 1.5 appeared first on SaaStr.

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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.

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Sales Hiring Sales Recruiting Scale Scaling 293

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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Sales Hiring Scale Sales Interviewing 197

SaaStr

AUGUST 23, 2024

Dear SaaStr: Growth Has Slowed and My VP of Sales is Pushing Me To Hire More Reps. In fact, the #1 sign your VP of Sales is really struggling is when their best answer to slowing sales is to hire even more sales reps. As if more humans, on their own, magically equal more sales. Not 9+ times out of 10.

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SaaStr

JANUARY 19, 2024

He made many great leadership points, but one in particular rattles around my head a lot and I think deserves its own post: You usually won’t know if you’ve made a 10x hire … when you make the hire. But I didn’t know they were truly 10x hires. Hire the very, very people you can. They more often rise up. months later.

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SaaStr

JULY 11, 2024

How Do You Sift Out the Bitter and Broken Individuals When Hiring? If it’s a role you’ve never hired, find someone great at it and have them do your final interview. For sales, product, or customer success, the best question you could ask is, “What would you do your first couple of weeks?” Don’t hire those people to lead.

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Sales Hiring Scale Marketing Interviewing 220

SaaStr

MARCH 18, 2024

Dear SaaStr: If you were hiring a head of sales for a high-priced, niche B2B SaaS product, would you focus on general B2B SaaS sales experience or on market/customer knowledge, assuming it will be very difficult to find a candidate with both? You’ll be very tempted to hire someone with a seemingly magical rolodex.

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Sales Hiring Sales SaaS B2B 287

SaaStr

AUGUST 17, 2024

Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales? In theory, why not let sales “keep” the customer longer? Even if having a CRO own post-sales and CS is becoming much more common these days. A “true” VP of Sales often wants nothing more to do with a customer after a deal closes.

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Sales Hiring Sales Customer Success Revenue 291

SaaStr

NOVEMBER 17, 2024

3 Came from the Investment Bank They Hired. In my experience, hiring an investment bank to help you in any acquisition > $100m or so is critical. But Andy got 3 other firm offers through the bank he hired — along with a price more than $10m higher. They lost their entire sales team, except one exec.

Sales Hiring 272

Sales Hiring Banking Sales SaaS 272

SaaStr

AUGUST 7, 2024

Dear SaaStr: Our VC Is Encouraging Us to Hire Aggressively and Increase the Burn Rate. Most of the first-time founders I’ve invested in aren’t “spending enough” in that they are a bit too slow to make accretive hires. The best version of this advice is to help founders learn where to make certain hires faster.

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Sales Hiring Venture Capital Investment Customer Success 197

SaaStr

JUNE 8, 2024

So David Obrand, CEO of Salesloft, had a great post the other day on consistency being one of the biggest challenges with enterprise sales. In SMB sales, you see the variance in performance among reps really fast, and you can take action fast. That’s the nature of a very short sales cycle. The best VPs of Sales know this.

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Sales Hiring Scale Sales SMB 260

SaaStr

NOVEMBER 3, 2024

I’m not talking about any close friends in sales here. But — there are a ton of folks I know that used to be great in sales. The other day someone who used to be an A+ sales leader emailed me about a position I’d introduced to him as a super hot start-up. And you just might want to hire him.

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Sales Hiring Sales Interviewing Startup 263

SaaStr

MARCH 16, 2023

A rough structure from 1–25 sales reps: Early days: CEO acts as VP of Sales. CEO hires 2 reps, in the beginning, each barely pays for themselves, but by months 4–6 they are able to close 3x or more of their total compensation. CEO often struggles to manage so many directly, trains them poorly. This is a rough guide.

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Sales Hiring Scale Startup Compensation 301

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. Product-Led Growth (PLG) vs. Enterprise Sales: Jason discusses the evolution of PLG, noting that it’s essentially freemium with better analytics.

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Sales Hiring Outsourcing Services Scale Interviewing 190

SaaStr

AUGUST 12, 2024

Probably the biggest challenge in vertical SaaS I see is scaling the sales team. It’s pretty easy to hire SaaS sales execs to sell … a SaaS sales product. But who do you hire to sell a very complex piece of vertical software? So if you hire reps for standard B2B companies, they often literally close nothing.

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Sales Hiring Scale Sales SaaS 262

SaaStr

OCTOBER 18, 2024

You can talk about the roadmap or sales strategy until you’re blue in the face, but if you don’t have the team to do it at scale, there’s no point in talking a ‘big game.’ ” The best sales leaders are the ones that are even better recruiters than the CEO. It’s recruiting five or six.”

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Sales Recruiting Sales Hiring Scale AI 252

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.

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SaaStr

FEBRUARY 19, 2024

and Lenny asked us to join his podcast to talk about building a sales team — from the perspective of a product-first founder or exec. It was a pretty strong conversation and we took a lot of our learnings over the years and focused on how to learn to do sales right if you come from a product-first background: It’s good.

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Sales Hiring Scale Sales Headcount 259

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.

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