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. Heres what Id look at: Pipeline Growth : Have they increased your pipeline metrics?

Sales Hiring 171

Sales Hiring Scale Sales Onboarding 171

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 344

Sales Hiring Headcount Engineering Banking 344

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 316

Sales Hiring Investment Leadership Startup 316

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 306

Sales Hiring Scale Scaling Sales 306

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 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 298

Sales Hiring Sales Management Metrics 298

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 299

Revenue Scale Sales Hiring Compensation 299

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 165

Sales Recruiting Sales Hiring Sales Leadership 165

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 290

Sales Hiring Scale Headcount Acquisition 290

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 264

Sales Hiring Sales Recruiting Scale Sales 264

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 207

Sales Hiring Marketing Technical Review Underperforming Technical Team 207

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 259

Sales Hiring Part-Time VPE CTO Hire Sales Recruiting 259

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

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 252

Part-Time VPE Sales Hiring Sales Recruiting Metrics 252

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

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 240

Sales Hiring Sales Recruiting Scale Sales 240

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 263

Sales Hiring Product Marketing Scale Marketing 263

SaaStr

OCTOBER 18, 2019

I still see most startups way behind on their 2020 planning, and most importantly, hiring, at this point in the year. Actual GAAP revenue, real recognized revenue is, has, and always will be, your primary metric. Second, you have to try to hire as many of the sales reps you’ll need for the end of Q1 … by mid-Q4.

Sales Hiring 242

Sales Hiring Scale Headcount Revenue 242

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 191

Scale Sales Hiring Scaling Headcount 191

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 315

Sales Recruiting Sales Hiring Scale Metrics 315

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 324

Sales Hiring Scale Sales Scaling 324

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 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 278

Sales Hiring Scale Churn Metrics 278

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 279

Sales Hiring Metrics Sales Churn 279

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

MAY 8, 2024

Let’s jump right into this set of community questions focused on SaaS metrics, growth, and efficiency. What metrics should we expect in this environment? Sales is much harder than in 2021. Therefore, sales and marketing practices made no sense in 2020. How Does That Impact Sales and Marketing?

Metrics 276

Metrics Scale Sales Hiring SaaS 276

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 294

Sales Hiring Scale Sales Interviewing 294

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 342

Sales Hiring Sales Retention Churn 342

SaaStr

JULY 8, 2024

How much more could you accomplish with your sales organization? Justworks CRO, Robert Lopez, and Director of Sales, Valeria Avila, show you how to create longevity in your sales organization and why it matters. If you’re hiring great people and giving them the tools to succeed, get out of their way. They’ll step up.

Sales Hiring 293

Sales Hiring Scale Sales Education 293

SaaStr

JULY 20, 2024

Metrics, Metrics, Metrics The first thing Secureframe thinks about is metrics. If you don’t know your key company or North Star metrics, talk to your investors or other experts to figure out what they should be. So they can take action on the metrics in real time if they’re going in a direction they don’t like.

Sales Recruiting 304

Sales Recruiting Sales Hiring Scale Engineering 304

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 316

Sales Hiring Sales Recruiting Scale Outbound Sales Team 316

SaaStr

NOVEMBER 20, 2024

Other places this feedback loop worked well were: Adoption loop metrics. Customers crave metrics about how teams are using all AI products. Other Learnings in the GTM Journey GitHub has had to adjust to new sales stages and new buyer personas. Deciding where you don’t want to spend your time.

Scale 264

Scale AI Scaling Marketing 264

Tom Tunguz

MAY 31, 2021

The cost of a failed account executive hire is about 8 months of lost productivity. What does it cost the organization to hire the wrong executive? In terms of time cost to the startup, a failed executive hire is roughly similar, 9 months. Hiring takes longer and is less fruitful. Looker was one of those examples.

Sales Hiring 197

Sales Hiring Sales Recruiting Startup Branding 197

SaaStr

DECEMBER 13, 2023

Dave Kellogg, EIR at Balderton Capital and 25-year C-level veteran, shares the top 14 signs that you have a SaaS metrics problem, the five reasons those symptoms exist, and a SaaS metrics maturity model with five layers to help you move the needle at every stage. The 15 Types of Misuse and Abuse of SaaS Metrics #1: Bludgeoning.

Metrics 340

Metrics Sales Hiring Benchmarks SaaS 340

SaaStr

JANUARY 21, 2020

Justin Welsh, former SVP of Sales at PatientPop explains how he started in SaaS in 2009 as the second sales hire at Zocdoc. Justin used Sales Culture to grow a successful PatientPop team to 140 employees and 55 million in revenue. Justin Welsh | SVP Sales @ PatientPop. Want to see more content like this?

Sales Recruiting 332

Sales Recruiting Sales Hiring Scale Sales 332

SaaStr

JANUARY 31, 2022

Having learned from thousands of customers and prospects, Sarah Lash, Envoy’s head of enterprise sales, will talk about what it takes to guide and scale enterprise sales programs during an uncertain future. Metrics That Matter. In my first six months at Envoy , I grew the sales team from six to 17. Hiring For Growth.

Sales Recruiting 246

Sales Recruiting Sales Hiring Scale Enterprise 246