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.

Sales Hiring

SaaStr

OCTOBER 11, 2024

ARR and is looking to hire an experienced COO how much equity should they give him/her? You should find, hire, and manage the VPs of Sales, Marketing, Customer Success, Product and Engineering and even Finance yourself. ARR is Hiring a COO, How Much Equity Should They Get? Dear SaaStr: If a startup is at $1.5M

Sales Hiring

SaaStr

MAY 3, 2025

Dear SaaStr: From 0 to $10m ARR, At What Point Do We Start Hiring and Whom? From 0 t o $ 10M ARR, the hiring roadmap is critical because every hire has a disproportionate impact on your trajectory. Heres how Id break it down: 0 t o $ 1M ARR: Founder-Led Everything Sales : Founders should lead sales.

Sales Hiring

SaaStr

JUNE 12, 2025

Dear SaaStr: When Should I Hire My First AE? We’re said this many times over the years at SaaStr, and it’s as true today as then: You should hire your first AE (Account Executive) once you’ve closed at least 10-20 customers yourself as the founder. Hire someone scrappy, hungry, and willing to learn.

Sales Hiring

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

SaaStr

JUNE 13, 2025

” I saw a term sheet the other day where a leading VC firm reserved $1m of the round … for hiring a “VP of AI” Leadership teams scrambling to post job descriptions for “Head of Artificial Intelligence.” Would you hire a “VP of Internet” in 2010? Think about it.

Sales Hiring

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

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

SaaStr

AUGUST 4, 2025

Dear SaaStr: What Do I Look For In My First Marketing Hire? Hiring your first marketing leader is a pivotal moment, and it’s easy to get it wrong if you don’t approach it strategically. The vast, vast majority of “marketers” are just not the right fit to be your first marketing hire and leader. And Hire That.

Sales Hiring

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

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

SaaStr

AUGUST 6, 2025

Dear SaaStr: What Are Some Top Tips for Hiring and Retaining Top Leaders? Hiring and retaining top leaders is one of the most critical things you’ll do as a founder or CEO. The best leaders will transform your company, but the wrong hire can set you back months—or even years. But mediocre VPs only talk about process.

Sales Hiring

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

SaaStr

JULY 23, 2025

Managing revenue operations (RevOps) in a SaaS company is all about aligning sales, marketing, and customer success to drive growth efficiently. Align Sales, Marketing, and Customer Success These teams need to work as one unit. If you can afford it, hire this role even earlier.

Sales Hiring

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

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

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

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

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

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

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

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

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

SaaStr

JULY 3, 2025

Dear SaaStr: How Long of a Ramp Period Should I Give a New VP of Sales? Everyone else … looks a little lost when they start 😉 For a Head of Sales at a seed or Series A startup, you should give them one full sales cycle —usually 90 days—to show meaningful progress. Not to quadruple sales, but to tilt the curve for real.

Sales Hiring

SaaStr

JULY 22, 2025

Dear SaaStr: What Are Your Top Tips to Building A First Sales Team? When it comes to sales hires, the key is to approach it methodically and avoid common pitfalls. Here’s how I’d break it down: Hire Two Reps to Start. Always hire at least two sales reps initially. Hire Reps You’d Buy From. For real.

Sales Hiring

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

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

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

SaaStr

JULY 20, 2025

As CRO of Databricks, he’s built one of the most successful developer-focused sales organizations in the world. Hiring Non-Technical Sales Leaders for Technical Products The Mistake : Founders think great sales skills translate to any market. “They want salespeople who can add value on the technical front.

Scale

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

SaaStr

JULY 14, 2025

Dear SaaStr: How Do I Know If My New VP of Sales is Working Out? This is one of the most discussed topics on SaaStr, and a deep dive here: The 30-Day Test: How to Know if Your VP of Sales Will Succeed In a nutshell, you’ll know if your VP of Sales is working out by looking at two things: results and team-building ability.

Sales Recruiting

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

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

SaaStr

AUGUST 8, 2025

Dear SaaStr: I’m Joining a B2B Startup at $3m ARR as VP of Sales. Stepping into the VP Sales role at a company with $3M ARR is a pivotal moment. Sales Team : How many reps are there, and what’s their productivity? Processes : Are there anyrepeatable sales and customer success processes in place, or is everything ad hoc?

Scale

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