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?

Scale 233

Scale Sales Hiring Scaling Marketing 233

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 260

Sales Hiring Scale Underperforming Technical Team Sales 260

SaaStr

OCTOBER 18, 2024

“The best hack,” Jason adds, “is not recruiting one management team. 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.’ It’s recruiting five or six.”

Sales Recruiting 305

Sales Recruiting Sales Hiring Scale AI 305

SaaStr

JUNE 23, 2025

Should I Stop Hiring? But … if growth remains strong and the burn rate overall is manageable and isn’t growing out of control, maybe don’t fully tap the brakes. That’s not a reason to stop or slow hiring. Evaluate Your Sales Efficiency Are your sales reps hitting quota?

Sales Hiring 169

Sales Hiring Scale Investment Acquisition 169

SaaStr

AUGUST 26, 2022

Who we’re hiring for at SaaStr: Director of Account Management to support our top sponsors. The post Who We’re Hiring for Team SaaStr: Director of Account Management, and Director of Email / Growth Marketing appeared first on SaaStr. Ideally has some services or agency CS experience, not just SaaS.

Sales Hiring 58

Sales Hiring Growth Marketing Management Marketing 58

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. VCs love VP of Sales that sell up well.

Sales Hiring 350

Sales Hiring Scale Sales Interviewing 350

SaaStr

JUNE 19, 2025

Dear SaaStr: How Do I Get a Job as a First Time VP of Sales? If you’re aiming to land a VP of Sales role, you need to position yourself as someone who can deliver results and scale a team. "The "The biggest mistakes CROs and VPs of Sales make when they take a new role." A VP of Sales’ #1 job is building a team.

Sales Recruiting 211

Sales Recruiting Sales Hiring Scale Development Team Review 211

SaaStr

FEBRUARY 11, 2021

In SaaS, #1 most common misfire, with a bullet, is the VP/head of sales. It goes something like “You’ve Got to Get Past the Carcass of Your First VP of Sales” or “It’s The Second VP of Sales When You Really Start Selling” or variants thereof. Because in SaaS start-ups, it seems like the majority of first VP Sales fail.

Sales Hiring 363

Sales Hiring Scale Sales Recruiting Sales 363

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

MAY 26, 2025

So what does that mean for inside sales? A 50/50 Sales Team. At least for SMB and more routine mid-market sales. By 2026, these same AI systems will have evolved to manage entire sections of the sales process autonomously. An A+ AI will soon join every sales call, for real. You’ll Need to Manage Both.

Scale 236

Scale Sales Hiring AI Sales 236

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.

Sales Hiring 349

Sales Hiring Sales Recruiting Scale Marketing 349

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 284

Sales Hiring Scale Marketing SaaS 284

SaaStr

JUNE 22, 2025

Dear SaaStr: I’m a Seed Stage, First Time VP of Sales. Don’t wait to hire an SDR team—start building pipeline immediately. Use tools like LinkedIn Sales Navigator, Apollo, or ZoomInfo to find leads. Sell the First $1M Yourself At this stage, you’re not just managing—you’re selling. What’s the sales cycle?

Sales Hiring 204

Sales Hiring Sales Recruiting Sales Metrics 204

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 261

Sales Hiring Scale SaaS AI 261

SaaStr

FEBRUARY 25, 2022

Dear SaaStr: How Many More Junior Marketers Should you Hire Before Hiring a VP of Marketing? In fact, one of the 10 most unforced errors I see founders make is hire someone too junior to get marketing going. If you are say $500k in ARR, you can’t hire a CMO that needs a team of 15-20 around her/him. They may have helped.

Sales Hiring 337

Sales Hiring Marketing Revenue Sales 337

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.

Scale 195

Scale Sales Hiring Sales Outsourced Development 195

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 260

Sales Hiring CTO Hire Scale Startup 260

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 230

SaaStr

JUNE 19, 2025

✨ Lemkin (@jasonlk) June 16, 2025 The Top 3 Reasons AI Sales Tools “Don’t Work” (Spoiler: They Actually Do, If You Use The Tools Properly) I get this question at least 3x a week: “Jason, we tried AI sales tools and they just don’t work. I’ve been in B2B and Saa sales for 15+ years.

Scale 269

Scale AI Sales Hiring Sales 269

SaaStr

JULY 1, 2025

Insights from Jasper Carmichael-Jack, CEO of Artisan at 2025 SaaStr AI Summit About Artisan: AI-powered sales platform building the end-to-end solution —from marketing personalization to AE automation across the entire revenue cycle. Sales is messier. CRM data accuracy sits at 47% across most sales orgs.

Scale 207

Scale Software Review Sales Hiring AI 207

SaaStr

JULY 1, 2025

Dear SaaStr: I’m Joining a Start-Up as Head of Sales At Just $1m ARR. Don’t wait to hire an SDR team—start building pipeline immediately. Use tools like LinkedIn Sales Navigator, Apollo, or ZoomInfo to find leads. What’s the sales cycle? Hire Slowly, But Hire Right Don’t rush to hire a big team.

Sales Hiring 179

Sales Hiring Sales Recruiting Sales Metrics 179

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 303

Sales Hiring Sales Interviewing compliance 303

SaaStr

JUNE 29, 2025

Here’s how early-stage founders should approach it: Hire Early, Even Before It Feels Necessary Don’t wait until churn becomes a problem. Customer Success should be a single-digit hire—ideally, your first 5-10 employees should include at least one CS hire. You will run out of time to do this right as founders.

Sales Hiring 189

Sales Hiring Customer Success Scale Churn 189

SaaStr

JULY 11, 2025

Later, it’s about building a repeatable sales process and ensuring your infrastructure can handle the growth. Burn Rate and Cash Management: Managing cash burn is a constant concern for almost all of us. Hiring the Right Team: A lot of founders wait too long to hire great VPs—VP of Sales, VP of Marketing, VP of Engineering.

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Scale Part-Time VPE Scaling Sales Hiring 227

SaaStr

JUNE 29, 2025

The Pivot : They interviewed 200 companies and 400 founders in just 6 weeks, asking one simple question: “If you’re open to hiring internationally, what are your biggest challenges?” Scaled Sales Without Revenue Operations (And Paid Dearly) The Explosion : From 2 AEs to 50 AEs in one year. ” Training was broken.

Payment Services 179

Payment Services Sales Hiring Payment Solutions SaaS Payments 179

SaaStr

MAY 10, 2025

A good playbook for customer success is all about driving retention, expansion, and customer happiness while making it scalable: Hire Truly Product-Savvy Customer Success Managers at First Focus on hiring people who customer-focused product nerds to start. Measure time-to-value and/or time-to-go-live. Be careful here.

Sales Hiring 232

Sales Hiring Customer Success Scale Retention 232

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 303

Sales Hiring Sales Recruiting Sales Interviewing 303

SaaStr

MAY 29, 2025

At SaaStr + AI Summit 2025, Jason Lemkin and Kyle Norton CRO of $1B+ vertical SaaS leader Owner (where Jason is on the board) did a deep dive on AI in Sales today. This isn’t about being an AI expertit’s about demonstrating active engagement with AI tools and genuine interest in how they can transform sales outcomes.

Sales Hiring 231

Sales Hiring Underperforming Technical Team AI Scale 231

SaaStr

OCTOBER 1, 2022

What almost never works, somewhat surprisingly, is hiring a Director of Outbound as your first outbound hire. And especially, a new VP of Sales comes in without real outbound experience. So they naturally look for a leader to start, a Director of Outbound that has built and managed an outbound team before.

Sales Hiring 306

Sales Hiring Scale Sales Startup 306

SaaStr

FEBRUARY 26, 2025

Is That Too Many Management Layers? If your VP of Sales is your closer, you have a VP of Accounts, and a VP of CS who is going to manage them all? If your VP of Sales is your closer, you have a VP of Accounts, and a VP of CS who is going to manage them all? Is That Too Many Management Layers?

Sales Hiring 198

Sales Hiring Startup Management SaaS 198

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 292

Sales Hiring Sales Management Metrics 292

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.

Sales Hiring 273

Sales Hiring Scale Sales Startup 273

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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Sales Hiring Consulting SaaS Strategy 318

SaaStr

MARCH 4, 2021

But, I know many of you have never hired a head of marketing before. And if you hire the wrong type — the more common type — then instead of more customers, you may end up with just a bunch of Blue Pens with your logo on them. Which means there’s a real brand to manage. That hire fails. All good stuff.

Sales Hiring 357

Sales Hiring Scale Marketing Branding 357

SaaStr

FEBRUARY 7, 2025

His view is your sales team teaches your customers how to get value out of your product. Ron explains: “Wehire mostly technical backgrounds, but as our customers get larger and larger, you start to get global account managers, and they’re going to have much more business strategic account management experience.

Scale 176

Scale Sales Hiring Scaling Revenue 176

SaaStr

JUNE 17, 2025

Dear SaaStr: What Are Some Tips For Shortening Enterprise Sales Cycles? A bit more on that here : How to Cope With Long Sales Cycles But there are plenty of things that help : Hire a VP of Sales with Enterprise Experience : A great VP of Sales who’s closed deals at your price point can shave months off your sales cycle.

Sales Hiring 169

Sales Hiring Enterprise Sales SMB 169

SaaStr

SEPTEMBER 26, 2022

Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $5m ARR, and ideally, Sales and Marketing well before that.

Sales Hiring 284

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 284