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. And relentlessly bring it down. It combines renewals, churn, and upsells.

Sales Hiring 231

Sales Hiring Customer Success Scale Retention 231

SaaStr

OCTOBER 20, 2020

Who should you hire, with limited budget? A VP of Sales? A truly great hire is >always< accretive. Hire anyone truly great you can find. And he was proud he’d just hired a VP of Sales at a below-market rate. You don’t want to save money on a great hire. In Just 2 Sales Cycles.

Sales Hiring 343

Sales Hiring Headcount Engineering Banking 343

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 227

Sales Recruiting Sales Hiring Scale AI 227

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 228

Sales Hiring Underperforming Technical Team AI Scale 228

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 187

Scale Sales Hiring Sales Compensation 187

SaaStr

APRIL 1, 2023

On the hiring side, it often seemed like you just couldn’t hire anyone. Everyone was hiring everyone, anyone, back in mid-2021. We hired job hoppers that never stayed anywhere for more than 18 months for leadership roles. The post Lowering the Hiring (And Investing) Bar Didn’t Work appeared first on SaaStr.

Sales Hiring 312

Sales Hiring Investment Leadership Startup 312

SaaStr

OCTOBER 7, 2020

As you scale up in SaaS, one thing I can almost guarantee is that you are going to hire some VPs who were either fired or quit their last role. But often, they don’t really have all the data and metrics, or even really know what they are getting themselves into. You’re still going to hire VPs with some of these flags.

Sales Hiring 362

Sales Hiring Scale Interviewing Startup 362

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 301

Sales Hiring Scale Scaling Sales 301

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

JUNE 8, 2025

Dear SaaStr: I Fired My VP of Sales. Here’s what you should do next: Step in as Interim VP of Sales (If Needed) If you don’t have someone ready to step up, you’ll need to take the reins yourself temporarily. You know the product, the customers, and the sales process better than anyone else. What you do need to do is have a plan.

Sales Hiring 140

Sales Hiring Sales Recruiting Sales Interviewing 140

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 293

Revenue Scale Sales Hiring Compensation 293

SaaStr

MAY 24, 2025

If you can maintain this pace and improve your metrics (like NRR and sales efficiency), you could still build a significant, valuable B2B business over time. Fundraising and Hiring Challenges Raising a Series A or B at 35% growth will be essentially impossible. However, youll need to be patientits a slower path.

Sales Hiring 192

Sales Hiring B2B Churn Retention 192

SaaStr

SEPTEMBER 19, 2021

If you want to hit the plan for Q1'22, You need to be hiring all the sales reps you'll need then … Now. To make the hires you need now, for next year. But you have to hire them NOW, not in January. How many Customer Success Managers. — Jason BeKind Lemkin (@jasonlk) September 15, 2021.

Sales Hiring 284

Sales Hiring Scale Headcount Acquisition 284

SaaStr

MARCH 22, 2022

This requires effort from your entire organization, and Handshake VP, Employer Partnerships Jessica Peluso outlines some changes that you can make to your brand, and your application, interview, and offer process that will help find the talent you are trying to attract and hire. Below is the transcript of Jessica’s session. Hi everyone.

Sales Hiring 261

Sales Hiring Sales Recruiting Scale Sales 261

SaaStr

NOVEMBER 27, 2021

Is your CS team growing as fast as your sales team? If this is your first SaaS company, you may not have ever hired or built a Customer Success team. This one isn’t nearly as risky as a VP of Sales , or a VP of Marketing hire. You’ll make a good hire. So hire your first as soon as you can. >>

Sales Hiring 246

Sales Hiring Customer Success Scale Customer Lifetime Value 246

SaaStr

OCTOBER 9, 2020

A VP of Sales and Success A VP of Sales and Marketing A VP of Sales and Anything Else. Is usually not really a VP of Sales. Sales managers back when I never managed sales. For signs the prospective hire just won’t work out, no matter how strong they might look on paper.

Sales Hiring 257

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 257

SaaStr

NOVEMBER 27, 2021

Is your CS team growing as fast as your sales team? If this is your first SaaS company, you may not have ever hired or built a Customer Success team. This one isn’t nearly as risky as a VP of Sales , or a VP of Marketing hire. You’ll make a good hire. So hire your first as soon as you can. >>

Sales Hiring 245

Sales Hiring Customer Success Scale Customer Lifetime Value 245

SaaStr

JANUARY 23, 2025

You need: Sales leaders who understand complex, multi-stakeholder deals Customer success teams ready for high-touch support Legal expertise for enterprise contract negotiation Product leaders who can balance current needs with future vision Pro tip: Hire enterprise reps in pairs. If both succeed, you’re ready to scale.

Enterprise 244

Enterprise Sales Hiring Scale Outsourced Development 244

SaaStr

MARCH 12, 2025

The 4 Things Most Founders Get Wrong About Marketing: “We’re a product company, not a marketing company” – The hard truth is that 9 out of 10 B2B companies spend more on sales and marketing than R&D. Better to hire for your specific needs and stage. These “five-five” CMOs barely exist.

Sales Hiring 194

Sales Hiring Marketing Technical Review Underperforming Technical Team 194

SaaStr

APRIL 28, 2025

The Journey: From WiFi to IoT Fleet Management Sekar’s journey began unexpectedly when he joined Meraki (founded by MIT researchers Sanjit Biswas and John Bicket) to help them figure out marketing and sales “from first principles.” Now well above $1.3B The Five Lessons 1.

Scale 260

Scale Transportation Scaling SMB 260

SaaStr

MAY 5, 2021

Did you hire a good enough VP? 4 part test: – who great did they hire in the first 60 days? – did their #1 key metric improve? Hiring your VPs as a founder is tough. How do you know, quickly, if you’ve hired a “good enough” VP? Criterion #2: Did their #1 key metric improve?

Part-Time VPE 233

Part-Time VPE Sales Hiring Sales Recruiting Metrics 233

SaaStr

SEPTEMBER 25, 2020

379: From how many reps to hire, to compensation models, here are the top 10 mistakes founders make when hiring their first sales teams and how to avoid them. Announcer: In today’s SaaStr Insider, SaaStr CEO and founder, Jason Lemkin, shared the top 10 mistakes founders make when hiring their first sales team.

Sales Hiring 239

Sales Hiring Sales Recruiting Scale Sales 239

SaaStr

MARCH 24, 2025

Dear SaaStr: I’m Starting as a New VP of Sales. A new VP of Sales can add value immediately by focusing on a few critical areas that drive results and demonstrate leadership from day one: Assess and Support Top Performers : A great VP of Sales will immediately identify the top-performing reps and double down on them.

Sales Recruiting 155

Sales Recruiting Sales Hiring Sales Leadership 155

SaaStr

FEBRUARY 2, 2023

Product marketing can be difficult, and managing product launches and rollouts can be complex. Your sales rise to a very high level You may realize that your sales are reaching high levels, but at the same time, you may encounter a situation where there needs to be more structure or control in your sales process.

Sales Hiring 260

Sales Hiring Product Marketing Scale Marketing 260

SaaStr

MAY 22, 2025

Dear SaaStr: How Can I Crush a VP of Sales Interview? To nail a VP Sales interview, you need to demonstrate that youre not just a smooth talker with a great LinkedIn profileyou need to show youre the real deal. Too many VPs of Sales and CROs show up to interviews knowing almost nothing about the product.

Sales Recruiting 194

Sales Recruiting Interviewing Sales Hiring Scale 194

SaaStr

MARCH 5, 2025

In our most recent episode of CRO Confidential , hosted by Sam Blond , Graham Moreno , VP of Worldwide Sales at Codium, shared invaluable insights on what drove this growth, the challenges they faced, and how other SaaS companies can replicate this success. Their strategy?

Sales Hiring 178

Sales Hiring Scale Sales Recruiting AI 178

SaaStr

NOVEMBER 8, 2024

Clay has raised $50M with a $500M valuation, and they only have 55 people on the team at this point, a lean company compared to other startups with the same valuation metrics. They’ve achieved this due to the systems they’ve set up and the profiles they’ve hired for. So let’s dive in. They’re trying to grow.

AI Search 274

AI Search Sales Hiring AI Systems Review 274

SaaStr

SEPTEMBER 1, 2021

Really, what you tend to see when you keep a stretch VP too long in their current role is flat metrics. For example, a great Stretch VP of Sales might get you to from $50k to $500k a month in new bookings. But if it goes one for more than a sales cycle, or a few releases, it’s time to bring in the VP for the next stage of growth.

Sales Recruiting 311

Sales Recruiting Sales Hiring Scale Metrics 311

Tom Tunguz

JULY 13, 2022

Yesterday, Office Hours welcomed Lars Nilsson, VP Sales Development from Snowflake to talk about his learnings across 5 companies he helped take public. Throughout the hour, Lars provided insightful perspectives on how to build sales organizations. Then, many founders opt to hire an AE. Hire for hunger.

Scale 324

Scale Sales Hiring Development Sales 324

SaaStr

JUNE 28, 2020

A debate so many start-ups go through is what to do about a Just OK VP of Sales they’ve hired. The VP of Sales turns out to be OK, but great. A Great VP of Sales has an immediate impact and closes much more than before she started. A Bad VP of Sales sees bookings decline. Like in one sales cycle.

Sales Hiring 313

Sales Hiring Scale Sales Scaling 313

SaaStr

JUNE 13, 2022

Metrics are critical in SaaS, and you need to track them fastidiously. But it’s also important to focus on the right metrics, at the right stage, and not obsess about the less important ones at the wrong times. Yes, long sales cycles are worse than short sales cycles. Customer Lifetime Value is just Churn inverted.

Sales Hiring 274

Sales Hiring Scale Churn Metrics 274

SaaStr

MARCH 11, 2021

Congratulations on finally hiring your VP of Sales! There are 3 general options: Your VP of Sales is responsible for net new revenue only. Post-sales, other than upsell which adds to net new revenue for this year, is someone else’s job. Your VP of Sales is responsible for the ARR target for the end of the year.

Sales Hiring 274

Sales Hiring Metrics Sales Churn 274

Tom Tunguz

APRIL 14, 2020

Sam Jacobs created the Revenue Collective , a group of more than 1700 sales professionals at some of the fastest-growing companies. With chapters across the US, Revenue Collective has broad reach within the sales community. Typically, sales leaders have reduced quota somewhere between 10-50%. You can download the survey here.

Sales Hiring 334

Sales Hiring Sales Forecasting Travel 334

SaaStr

MARCH 18, 2025

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 178

Scale Sales Hiring Scaling Headcount 178

SaaStr

APRIL 7, 2020

In the early days of SaaStr, we wrote a bunch of posts that were controversial at the time, but later, most sales leaders eventually agreed with. That you know even in 1 sales cycle if a VP of Sales is going to work out. As soon as you hear a VP of Sales start to blame her/his own reports for missing a number, it’s over.

Sales Hiring 341

Sales Hiring Sales Retention Churn 341

SaaStr

JANUARY 11, 2021

The moment comes when it’s time to hire your first VP Sales. We’ve talked in the past about the 48 Different Types of VP Sales , What a VP Sales Really Does , and even given you a Script to Use When Interviewing a VP Sales. So at this stage, the VP Sales, while necessary, sure looks expensive.

Sales Hiring 288

Sales Hiring Scale Sales Interviewing 288

SaaStr

JANUARY 5, 2024

In the latest episode of CRO Confidential, host Sam Blond, partner at Founders Fund and former CRO at Brex, sits down with Ashley Kelly, VP of Global Sales Development at Rippling. For context – Ashley had previously helped Sam scale Brex’s outbound sales from $2M to over $300M in ARR as Senior Director of SDR.

Sales Hiring 311

Sales Hiring Sales Recruiting Scale Outbound Sales Team 311