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 264

Sales Hiring Scale Underperforming Technical Team Sales 264

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 351

Sales Hiring Scale Sales Interviewing 351

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 290

Sales Hiring Scale Marketing SaaS 290

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 183

Scale Sales Hiring Scaling Revenue 183

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.

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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

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 265

Sales Hiring Scale SaaS AI 265

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

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

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 242

Sales Recruiting Sales Hiring Scale AI 242

SaaStr

NOVEMBER 20, 2024

At this year’s SaaStr AI Summit, GitHub CRO Elizabeth Pemmerl shared how to bring AI products to market at scale successfully. With 90% of the Fortune 100 on GitHub and 40% of its $2B revenue coming from AI products, these real-world examples will also help you launch an AI-powered product at scale. The next horizon is scaling.

Scale 265

Scale AI Scaling Marketing 265

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 264

Scale Transportation Scaling SMB 264

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 264

Sales Hiring CTO Hire Scale Startup 264

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 307

Sales Hiring Scale Scaling Sales 307

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 236

Sales Hiring Customer Success Scale Retention 236

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

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

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 205

Scale Sales Hiring Sales Outsourced Development 205

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 201

Scale Sales Hiring Sales Compensation 201

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 239

Sales Hiring Scale Banking Scaling 239

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 189

Scale Sales Hiring Scaling Headcount 189

SaaStr

JANUARY 12, 2025

4: What Really Works When Hiring VPs, and How M&A Really Works, with HubSpot Co-Founder and Chair Brian Halligan + Jason Lemkin #5: Whats Better, X/Twitter or LinkedIn? And 10%-12% of Ones That IPO. #4:

Sales Hiring 286

Sales Hiring Scale Scaling Revenue 286

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 279

Sales Hiring Scale Sales Startup 279

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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Sales Hiring Headcount Scale Cloud 329

SaaStr

JANUARY 27, 2022

Q1 is really your last chance to get the hires done you really need for 2022. Add 60-90 days for onboarding and scale-up, they’re at 100% strength by Q3. This is a pretty basic post, but one so many busy CEOs and founders just miss: It’s already almost too late to make the hires you need for 2022! How can this be?

Sales Hiring 318

Sales Hiring Scale Scaling Onboarding 318

SaaStr

OCTOBER 2, 2024

Dear SaaStr: Why Do Founders Hire So Many Terrible VPs that Mislead Them? It’s hard to scale if you don’t. 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. Needing a team.

Sales Hiring 291

Sales Hiring Scale Interviewing Engineering 291

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 311

Sales Hiring Scale Sales Startup 311

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 251

Sales Hiring Scale Scaling Engineering 251

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. Yes, you need it at scale — but not in the same ways startups do. All good stuff.

Sales Hiring 357

Sales Hiring Scale Marketing Branding 357

SaaStr

APRIL 8, 2025

Many of the early break out leaders in AI for B2B and otherwise have been “small but mighty teams” Honestly we’d all love it if that scaled. And thus — hiring more. They they are doubling down and hiring even more to keep these gains going. And can it sell and scale sales?

AI 288

AI Sales Hiring Scale B2B 288

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 280

Scale Sales Hiring Sales Headcount 280

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.

Sales Hiring 292

Sales Hiring Scale Marketing Interviewing 292

SaaStr

JULY 13, 2022

Q: Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit? My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit: #1: Full-time sales rep at $8k-ish MRR. I Should have hired two. I hired at $20k MRR.

Sales Hiring 291

Sales Hiring Product Marketing Scale Marketing 291

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

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 314

Scale Sales Hiring Scaling Innovation 314

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

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 300

Revenue Scale Sales Hiring Compensation 300