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?

Sales Hiring 287

Sales Hiring Sales AI Enterprise 287

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 304

Sales Hiring Sales Recruiting Sales Headcount 304

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.”

Sales Recruiting 308

Sales Recruiting Sales Hiring Scale AI 308

SaaStr

DECEMBER 20, 2024

Former Head of Revenue at BILL and HubSpot Americas leader Michelle Benfer recently joined us on a SaaStr Workshop Wednesday share her insights on one of the most critical roles in any SaaS organization: the frontline sales manager. “At HubSpot, I had over 100 frontline sales managers reporting to me.

Sales Hiring 262

Sales Hiring Scale Underperforming Technical Team Sales 262

SaaStr

MARCH 13, 2025

Dear SaaStr: Should I Let My VP of Sales Go? I’m Not Sure I’ve Made The Right Hire 60 Days In? All Your VPs Really Need to Do is Tilt the Curve A great VP of Sales should show meaningful progress within one sales cycle. Taking Work Off Your Plate : Have they taken ownership of sales?

Sales Hiring 169

Sales Hiring Scale Sales Onboarding 169

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.

Sales Hiring 287

Sales Hiring Sales Interviewing Startup 287

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 296

Sales Hiring Banking Sales SaaS 296

SaaStr

NOVEMBER 4, 2024

Dear SaaStr: What’s the #1 Reason You See Sales Reps Fail These Days? The #1 reason I see sales execs struggling today in new roles: they are convinced their playbook is better. And you have to run their playbook, 9 times out of 10, to succeed in sales. You are being hired in part for your experience.

Sales Hiring 287

Sales Hiring Sales 287

SaaStr

JANUARY 16, 2025

Workato’s SVP of Embedded Sales and Director of Solutions Marketing joined us at SaaStr Annual to talk about how to nurture customers — a great topic in general, but especially for embedded sales and APIs that can take a while to scale. The Second Most Important SaaS Hire? Customer Success. But the results?

Sales Hiring 246

Sales Hiring Scale Sales Churn 246

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”.

Sales Hiring 342

Sales Hiring Sales 342

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.

Sales Hiring 287

Sales Hiring Scale Marketing SaaS 287

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.

Sales Hiring 307

Sales Hiring Sales Recruiting Scale Technical Review 307

SaaStr

JANUARY 2, 2025

Have we lost interest in investing in the human side of sales? Not in hiring sales execs themselves, but in giving them more tools to be more efficient. AI has hardly rendered the sales professional obsolete. Salesforce itself is hiring 2,000 sales execs this year to sell its AI platform, AgentForce.

Sales Hiring 330

Sales Hiring Scale Headcount AI 330

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.

Sales Hiring 259

Sales Hiring AI Scale Compensation 259

SaaStr

OCTOBER 16, 2024

AI has ripped through categories like the post-sales space and customer support centers. You see this first point viscerally if you’re involved in post-sales or support. Sales is beginning to promise this. That might mean you hire fewer but better people. Settling is worse than hiring no one. You have to do it all.

Sales Hiring 320

Sales Hiring Scale AI SaaS 320

SaaStr

JANUARY 15, 2025

During a recent SaaStr Workshop Wednesday , Mangomint’s VP of Sales Marchelle Mooney shared 10 ways sales is different in vertical SaaS. Marchelle’s personal journey took her from early adopter of Mangomint, to 6 years later, VP of Sales over a 25+ person SMB sales team. Find the one that has felt the pain.”

Scale 276

Scale Sales Hiring SaaS Payments Sales 276

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 296

Sales Hiring Healthcare Growth Marketing Sales 296

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.

Sales Hiring 306

Sales Hiring Sales Interviewing compliance 306

SaaStr

DECEMBER 25, 2024

If you are sales-driven, youll usually stall out at $1.5m-$2m in ARR or so if you dont start growing the team to the next level, The First 50. Theres just physics here to get to $10m in ARR in a sales-led model, even a partially sales-led model: After $1.5m Youll need another sales rep at least per every $500k in new ARR.

Sales Hiring 263

Sales Hiring Scale SaaS AI 263

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.

Sales Hiring 306

Sales Hiring Sales Recruiting Sales Interviewing 306

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.

Sales Recruiting 179

Sales Recruiting Sales Hiring Scale AI 179

SaaStr

FEBRUARY 8, 2025

Every great hire starts before their first day And often even during the interview process — Jason SaaStr 2025 is May 13-15 Lemkin (@jasonlk) January 12, 2025 #1. The Best VPs Start Before They Start The best sales leaders start reaching out to a few great customers they already know. Struggling on whether or not to hire that VP?

Sales Hiring 268

Sales Hiring Interviewing Sales Marketing 268

SaaStr

DECEMBER 19, 2024

Go Hire That Missing VP! The best way to get out of a hole is to hire a great VP. A great VP of Sales. Well, stop saying you cant hire anyone. And just go finally hire her. Everyone lowered the hiring bar in the Boom. And whether you promote them or not, get extra stock grants to your Top 10% hires.

Sales Hiring 283

Sales Hiring SaaS Venture Capital Healthcare 283

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.

Sales Hiring 315

Sales Hiring Investment Leadership Startup 315

SaaStr

OCTOBER 13, 2024

I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. Or didn’t want to do sales. I still believe a CEO should “do it all” in terms of building a decent management team first before hiring a COO. Hiring a strong COO between Management Team 1.0

Sales Hiring 262

Sales Hiring CTO Hire Scale Startup 262

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.

Sales Hiring 310

Sales Hiring Sales Marketing 310

SaaStr

MARCH 17, 2025

Hire an Ex Post-Facto Co-Founder: This is someone who isnt technically a co-founder but acts like one. It could be a VP of Product, Sales, or Engineeringsomeone who takes ownership of a big chunk of the business and cares almost as much as you do. Prioritize Great Early Hires. If youre technical, hire someone who can sell.

Sales Hiring 249

Sales Hiring Scale Scaling Engineering 249

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.

Sales Hiring 287

Sales Hiring Scale Interviewing Engineering 287

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.

Sales Hiring 295

Sales Hiring Sales Management Metrics 295

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.

Sales Hiring 327

Sales Hiring Headcount Scale Cloud 327

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.

Sales Hiring 304

Sales Hiring Scale Scaling Sales 304

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.

Sales Hiring 290

Sales Hiring CTO Hire CTO Coach CTO 290

SaaStr

JANUARY 4, 2025

Ive discussed variants of this question with so many CEOs and also CROs and VPs of Sales. You cant get sales reps used to only doing inbox to magically start cold calling for real. You have to start with a certain set of expectations, and hire folks that want to meet them. Y ou gotta hire those folks from Day 1.

Sales Hiring 276

Sales Hiring Sales 276

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?

Sales Hiring 296

Sales Hiring Social Media Interviewing Education 296

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.

Sales Hiring 245

Sales Hiring Scale Sales Interviewing 245