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. Nothing else matters, right?

Sales Recruiting 300

Sales Recruiting Sales Hiring Scale AI 300

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. 50% of your team are humans.

Scale 213

Scale Sales Hiring AI Sales 213

SaaStr

NOVEMBER 20, 2024

GitHub, founded in 2008, is a leading platform for software development and version control that has made waves since 2018 with its AI Copilot. At this year’s SaaStr AI Summit, GitHub CRO Elizabeth Pemmerl shared how to bring AI products to market at scale successfully. The next horizon is scaling.

Scale 260

Scale AI Scaling Marketing 260

SaaStr

APRIL 28, 2025

Samsara was intentionally multi-product from the earliest days, and they carefully planned out scaling 5+ products to $100M+ ARR. At Samsara, they formalized this with practices like “Transportation Tuesdays” where 20% of sales capacity focused on transportation verticals.

Scale 258

Scale Transportation Scaling SMB 258

SaaStr

JUNE 15, 2025

Dear SaaStr: How Do I Hire a Great First 1-2 Sales Reps? Hiring your first AE (Account Executive) is a pivotal moment for your startup. "Never, ever hire a VP of Sales until you have 2 individual sales reps really closing. . "Never, And that early sales team? Hitting quota.

Sales Hiring 209

Sales Hiring Scale Sales Compensation 209

SaaStr

APRIL 8, 2025

Dear SaaStr: When Should I Hire Our First Sales Person, and Who Should I Hire? "The "The one cheat code to making your first sales hires. Because as a founder, you need to understand the sales process, the objections, and what resonates with your customers. Hire smarter.

Sales Hiring 170

Sales Hiring Scale Sales Pricing 170

SaaStr

FEBRUARY 7, 2025

With Databricks now one of the largest pre-IPO technology companies, with $10 billion of expected non-dilutive financing and a valuation of $62 billion, Ron’s insights are gold for any revenue leader looking to scale. His view is your sales team teaches your customers how to get value out of your product.

Scale 173

Scale Sales Hiring Scaling Revenue 173

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 232

Scale AI Sales Hiring Sales 232

SaaStr

JUNE 5, 2025

Dear SaaStr: What Are A Few Top Tips to Hiring The Right First VP of Sales? Hiring a great VP of Sales is one of the most critical decisions youll make as a founder. Get it right, and theyll scale your revenue and team. Heres how to approach it: Timing is Everything Dont hire a VP of Sales too early.

Sales Hiring 222

Sales Hiring Sales Recruiting Scale Sales 222

SaaStr

JUNE 1, 2025

Dear SaaStr: What are the most common mistakes first-time founders make when building enterprise sales teams? The most common mistakes first-time founders make when building enterprise sales teams are surprisingly consistent. Heres the breakdown: Hiring a VP of Sales Too Early : This is a classic.

Outsourcing Services 179

Outsourcing Services Sales Hiring Scale Enterprise 179

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

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 186

Scale Sales Hiring Sales Outsourced Development 186

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." Highlight your ability to scale.

Sales Recruiting 189

Sales Recruiting Sales Hiring Scale Development Team Review 189

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 260

Sales Hiring Scale SaaS AI 260

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.

Scale 176

Scale Sales Hiring Sales Compensation 176

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

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 280

Sales Hiring Scale Marketing SaaS 280

SaaStr

DECEMBER 19, 2023

Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? In the early days, it’s simply that you have a few more leads than you can currently handle. Plus — following up on the 50 qualified leads from the month before. To a point. appeared first on SaaStr.

Sales Hiring 297

Sales Hiring Scale Scaling Sales 297

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.

Scale 271

Scale Sales Hiring Sales Headcount 271

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. The 5 Key Elements of Codeium’s GTM Scaling Playbook 1. What is Codeium and Windsurf?

Sales Recruiting 211

Sales Recruiting Sales Hiring Scale AI 211

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 257

Sales Hiring CTO Hire Scale Startup 257

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 254

Sales Hiring AI Scale Compensation 254

SaaStr

MARCH 18, 2025

It’s an incredible look back on scaling and more: Colin Jones, first Chief Revenue Officer at Wiz. As Colin describes it, “I went to the CEO and asked to generate more revenue and hire more people, which is counter-intuitive to the standard approach where revenue leaders may sandbag to over deliver and crush numbers.”

Scale 170

Scale Sales Hiring Scaling Headcount 170

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 209

Sales Hiring Underperforming Technical Team AI Scale 209

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 299

Sales Hiring Sales Recruiting Scale Technical Review 299

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 145

Sales Hiring Scale Sales Onboarding 145

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

JANUARY 12, 2025

Top Posts: #1: 2025 And The Rise of the Mech AE (Account Executive) #2: 2025 Should Be Better Than 2024 For Almost All Leading Public SaaS Companies #3: 38% of Bootstrapped Start-Ups Have Solo Founders. But Only 17% of VC-Backed Ones Do. And 10%-12% of Ones That IPO. #4: appeared first on SaaStr.

Sales Hiring 273

Sales Hiring Scale Scaling Revenue 273

SaaStr

FEBRUARY 18, 2022

Sales-driven SaaS startups end up with about half their headcount in sales and marketing. Sales doesn't. One thing that sneaks up on you in SaaS is just how many sales, marketing and revenue professionals you are going to need: First it sneaks up on you in the early days because the initial tiny team become so efficient.

Scale 351

Scale Sales Hiring Scaling Headcount 351

SaaStr

JANUARY 19, 2025

We’ll hear from the CRO of $3B Clio (legal SaaS), the CEO and CRO of Flock Safety (police and safety SaaS), and dozens of others on how to scale their vertical SaaS industries and platforms. It takes getting out in the field, and creating a ton of true value — before the sale. #2. See you there! How Kyle does it here: #3.

Scale 189

Scale Sales Hiring Scaling SMB 189

SaaStr

JANUARY 8, 2025

When Lindsey joined, she inherited an already built-out self-serve/PLG model for small businesses and a mid-market and enterprise sales, customer success, and post-sales team. But at the start of its expansion play, Checkr’s enterprise motion failed, and sales cycles were slow, taking up to a year for $100k & up deals.

Revenue 290

Revenue Scale Sales Hiring Compensation 290

SaaStr

DECEMBER 13, 2021

It’s a bit of a bummer than oftentimes, once you finally hire a few great VPs at $1m, $2m, $3m ARR … and they do a great job … that they then don’t scale. A few signs I see again and again of VPs that can’t scale beyond $5m-$10m ARR: Lack of organization. But it doesn’t scale. They get it.

Scale 353

Scale Sales Recruiting Sales Hiring Scaling 353

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 226

Sales Hiring Customer Success Scale Retention 226

SaaStr

OCTOBER 10, 2023

On a sales front, how do you evolve past founder-led sales, or together with it, so that you can scale your organization? Founder-led sales can be an immense strength and rapidly become a limiting factor. PST, Laura Connell, Partner at Atomico, shares how to scale beyond founder-led sales on your path to Series B.

Scale 269

Scale Sales Hiring Scaling Sales 269

SaaStr

AUGUST 15, 2024

There’s always someone a few years ahead of you on the scaling journey who can share their lessons learned. Robbie O’Connor, the GM EMEA at Notion and the first European hire at Asana and Dropbox takes the stage at SaaStr Europa to talk about the building blocks required to scale GTM teams and operations. You can get this wrong.

Scale 302

Scale Sales Hiring Scaling Innovation 302

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 235

Sales Hiring Scale Scaling Engineering 235

SaaStr

MAY 25, 2025

Reasons To Should Raise Now: Hire Ahead of Growth : At this stage, every great hire is accretive. If youve got the cash to hire ahead of demandmore sales reps, SDRs, engineersyou can accelerate growth instead of waiting for revenue to fund those hires. But don’t just raise because you can.

Sales Hiring 214

Sales Hiring Scale Banking Scaling 214