SaaStr

JANUARY 19, 2025

Dear SaaStr: At What Point Should a Startup Hire a Salesperson? If you hire a salesperson before 10 customers. And when you do go to hire that first sales rep, at the very minimum, only hire someone you’d truly, honestly buy your own product from — yourself. Never before. After 10 you will know.

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Sales Hiring Startup Sales 246

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 291

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.

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Sales Hiring Scale Underperforming Technical Team Sales 264

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 311

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 291

SaaStr

APRIL 6, 2025

A little ways back Databricks VP of Sales Heather Akuiyibo joined SaaStr to share unexpected things that work well at Databricks GTM organization as well as some things that havent worked as well. Deep Dive: Unexpected Learnings Time Management as Competitive Advantage Most sales organizations guess how reps should spend their time. .”

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Scale Sales Hiring Sales Outsourced Development 208

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.

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Sales Hiring Sales 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.

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Sales Hiring Banking Sales SaaS 300

SaaStr

MARCH 16, 2025

Alex Rosenblatt was the first marketing hire and Chief Marketing Officer at Datadog, all the way through IPO and beyond. The 10th marketing hire is the most critical inflection point for team scaling – This is where informal processes break down and requires a complete rethinking of how the team operates. The problem?

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Scale Sales Hiring Scaling Marketing 249

SaaStr

APRIL 15, 2025

On everything from how to hire a great VP of Sales, to reviewing investor memos, to helping (many!) Not for selling per se, but for answering sales-related questions. So we do love our SaaStr AI. It’s not perfect, but in its first month alone, it’s answered over 6,000 chats and questions from the SaaStr community!

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Sales Hiring AI Sales B2B 299

SaaStr

MARCH 29, 2025

Dear SaaStr: What Are The Best Ways to Transition From The Founder-Led Sales Stage? Transitioning from founder-led sales to a commissioned sales team is one of the most criticaland trickysteps in scaling a SaaS business. You Never Get to Leave Sales. This is non-negotiableeven if you hate sales. Be specific.

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Scale Sales Hiring Sales Compensation 206

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?

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Sales Hiring Scale Sales Churn 246

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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Sales Recruiting Sales Hiring Scale AI 248

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?

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Sales Hiring Scale Sales Onboarding 171

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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Sales Hiring Sales 342

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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Sales Hiring Sales Recruiting Scale Technical Review 310

SaaStr

JANUARY 9, 2025

Dear SaaStr: What Are Some Successful SaaS Leaders Without Sales Teams? Many that are self-serve and SMB-focused can start off without a sales team … for a while. But almost none stay without a sales team … forever. Yes, Atlassian since well past its IPO had almost no direct sales team. Maybe on Day 0.

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Scale Sales Hiring Sales Headcount 280

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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Sales Hiring Scale Marketing SaaS 290

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 309

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. I think it’s still one of the best books on how to repeatably scale sales teams.

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Sales Hiring Sales Recruiting Scale Marketing 349

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 308

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.

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Sales Hiring Scale SaaS AI 265

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?

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Sales Hiring Interviewing Sales Marketing 272

SaaStr

APRIL 20, 2025

Dear SaaStr: How Should I Actually Set the Sales Plan for the Year For My VP Sales? This is where you build your operational model: sales hiring, marketing spend, product investments, etc. This is critical for managing your burn rate and ensuring you dont run out of cash. Try the C10, C60, and C90 framework.

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Sales Hiring Sales Communication Revenue 166

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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Sales Hiring Sales compliance Interviewing 192

SaaStr

APRIL 2, 2025

Dear SaaStr: How Long Should You Give a New Sales Rep? sales cycles. Sales is tough. And while sales is pretty similar in SaaS at a given price point / ACV, different products are still different to sell.A sales cycles, it rarely works out. But you do need to see some deals closing within a standard sales cycle.

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Sales Hiring Sales Onboarding Pricing 180

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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Sales Hiring Sales Management Metrics 299

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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Sales Hiring Healthcare Growth Marketing Sales 300

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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Sales Hiring AI Scale Compensation 261

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 245

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 307

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

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Sales Hiring CTO Hire Scale Startup 264

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.

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Sales Hiring SaaS Venture Capital Healthcare 287

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.

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Sales Hiring Sales 279

SaaStr

DECEMBER 31, 2024

Agentforce at Salesforce is Benioffs #1 push but its literally just getting started: Salesforce: Actually We’re Going to Hire 2,000 Sales Execs Now To … Sell AI Lets be clear: a lot of SaaS and B2B apps are still experimenting with AI. But it mostly is enhancing the classic product, near as I can tell.

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AI CTO Hire Sales Hiring CTO 331