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

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.

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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

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

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

DECEMBER 19, 2024

Salesforce, Nov 2024: We're hiring 1,000 new sales execs to sell AI! Well that must have gone well as Salesforce is now hiring 2,000 (!) in sales to sell AI. Per The Information , Benioff has also instructed his sales team to go all-in and put AI and Agentforce into every deal possible. Not really.

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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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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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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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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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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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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

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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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

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

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

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.

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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

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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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

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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SaaStr

JULY 3, 2023

Dear SaaStr: When Should You Hire Your First Demand Generation Marketer in SaaS? A deep dive on that and why here: I Hired My VP of Marketing at $20k MRR. In a recurring revenue model, you want to make every accretive hire you can. Or just hiring a junior marketer to start to save a few dollars. Even when you hire a VP.

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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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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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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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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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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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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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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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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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SaaStr

APRIL 7, 2024

So just a little while back, Lenny Rachintsky had me on his hyper-popular podcast to talk about scaling sales, from the perspective of a founder who hasn’t really done sales. They really are a great checklist when you are starting to scale sales in SaaS: #1. And sales go down, not up. #2. It’s a tough job.

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SaaStr

JUNE 10, 2024

So in the earlier days especially, you’ll be tempted to lean on the sales team to do more than just … sell. Especially because the first 1-2 successful reps you hire will often be a bit of a product expert, and be great at really understanding customer problems. It has some positives, the more you ask sales to do.

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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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SaaStr

FEBRUARY 12, 2024

And so many of you in fact are, well … hiring. Most of you are, in fact: According to our latest unscientific but directionally correct survey of over 2,000 SaaS execs, 64% of you are growing your sales team in 2024. Find those still hiring, and find 5 or 10 that truly are a match for your skills. Slow it down.

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SaaStr

NOVEMBER 29, 2024

It’s not the crazy hiring market of 2021. He just can’t find enough great folks to hire. It earned them special attention from others on the hiring panel + company leaders… — Brie Wolfson (@zebriez) November 26, 2024 Everyone great is hiring. But almost everyone growing even at “pretty good” rates is hiring.

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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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