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 31, 2025

Pre-Seed / Seed Stage (Pre-Revenue or <$1M ARR) At this stage, you’re compensating for high risk with high equity. Key hires like a VP of Engineering or VP of Product might get 1%-2% each. A good rule of thumb is to offer 2x-3x the equity you’d give at later stages to account for the risk. Executives : 0.3%-1%

Part-Time VPE 182

Part-Time VPE Sales Hiring Sales Recruiting Compensation 182

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 174

Sales Hiring Sales Recruiting Scale AI 174

SaaStr

OCTOBER 28, 2024

f you are starting from the ground floor, first, bear in mind your compensation will be just OK, you won’t really get any “carry” (i.e., Third, you are going to have to find some way to get really good at sales. And even if you did source Uber, well, the partner that manages the deal will likely take all the credit.

Sales Hiring 300

Sales Hiring Compensation Branding Investment 300

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

JANUARY 27, 2023

As the past few years have demonstrated, it’s wise to expect the unexpected, especially when it comes to hiring. In particular, hiring for your sales team is critical in an uncertain economic outlook. Additionally, sales professionals looking for a new role should choose their next company wisely.

Sales Recruiting 242

Sales Recruiting Sales Hiring Scale Compensation 242

SaaStr

MARCH 6, 2025

One of the classic original SaaStr posts was on the Top 10+ Questions to Ask a VP of Sales Candidate. It’s a different world today, AI-fueled, often distributed and hybrid, and with inflation both in titles (CRO or VP Sales) and compensation expectations. Use this updated script for hiring that first VP of Sales.

Sales Recruiting 184

Sales Recruiting Sales Hiring Scale Interviewing 184

SaaStr

MARCH 16, 2023

A rough structure from 1–25 sales reps: Early days: CEO acts as VP of Sales. CEO hires 2 reps, in the beginning, each barely pays for themselves, but by months 4–6 they are able to close 3x or more of their total compensation. CEO often struggles to manage so many directly, trains them poorly.

Sales Hiring 326

Sales Hiring Scale Startup Compensation 326

SaaStr

JULY 22, 2020

I’m not ashamed to admit that when I set up our first SaaS sales comp plan, I had no idea what I was doing. But I did all the sales myself, and stupidly, had no sales comp plan at all ??. Then, as we first scaled up a sales team, we ended up literally copying Salesforce’s comp plan. the Moment After Sale.

Scale 363

Scale Sales Hiring Sales SaaS 363

SaaStr

JULY 25, 2020

Q: What is a typical organizational structure for a SaaS startup with sales reps? A rough structure from 1–25 sales reps: Early days: CEO acts as VP of Sales. CEO hires 2 reps, in the beginning, each barely pays for themselves, but by months 4–6 they are able to close 3x-5x their total compensation.

Sales Hiring 302

Sales Hiring Scale Compensation Sales 302

SaaStr

NOVEMBER 8, 2024

They’ve achieved this due to the systems they’ve set up and the profiles they’ve hired for. With AI creating a cohesive message across the entire customer journey, we might see the ability to consolidate marketing, sales, and customer success. So let’s dive in. They’re a creative approach to GTM. They’re trying to grow.

AI Search 273

AI Search Sales Hiring AI Systems Review 273

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 236

Sales Hiring Sales Recruiting Scale Sales 236

Tom Tunguz

NOVEMBER 16, 2015

As he told me a few days ago, he has observed the lack of sales management and sales execution skills as one of the most consistent deficiencies limiting the potential of early stage SaaS companies. Sales execution deficiency manifests itself at roughly the same time as product market fit.

Sales Hiring 184

Sales Hiring Sales Recruiting Startup Compensation 184

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 318

Sales Recruiting Sales Hiring Scale Sales 318

SaaStr

DECEMBER 2, 2023

Dear SaaStr: What Is The Optimal Structure of an Initial SaaS B2B Sales Team? Where, roughly speaking, each sales rep brings in at least 4x-5x the total compensation they take out. Where you burn a ton of cash is “buying” sales. Shoving sales reps into segments where you don’t have enough leads / enough demand.

Sales Hiring 273

Sales Hiring Scale B2B Sales 273

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 284

Sales Hiring Scale Sales Education 284

SaaStr

APRIL 4, 2024

The post The Top 8 SaaStr Tips to Building an Effective First Sales Team (per Perplexity) appeared first on SaaStr. I think it did a pretty good job The summaries we do might be better, but this is a great place to start. I think it did a pretty good job The summaries we do might be better, but this is a great place to start.

Sales Hiring 279

Sales Hiring Scale AI Search Compensation 279

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 273

Scale Sales Hiring Scaling Sales 273

Tom Tunguz

NOVEMBER 24, 2018

You might have a few account executives and a sales leader in place; maybe some revenue and a handful of customers. The sales team costs real money, and the question before the company is: how do you know what quota plan to assign to the account executives? Stage 1: Management by Objectives.

Compensation 195

Compensation Sales Recruiting Sales Hiring Scale 195

SaaStr

AUGUST 7, 2020

A few factors that contribute to high-performing sales teams: High quota attainment. The best startups invest in their sales teams and work hard so most of the reps hit and exceed quota. It does mean a well-oiled machine that hires strong reps of all backgrounds, and gets them the help and training so they can scale up and succeed.

Sales Hiring 362

Sales Hiring Scale Sales Recruiting Compensation 362

SaaStr

DECEMBER 27, 2020

If the founders are the highest compensated people in the start-up, at least pre-Scale (e.g., So once you’ve raised a bit, if you make sure at least someone else on the team makes more than the founders … that great VP you just hired for example … you’ve probably found the right compensation level for you as CEO.

Venture Capital 343

Venture Capital Sales Hiring Scale Compensation 343

SaaStr

AUGUST 9, 2021

So how do you simplify and speed up your sales cycles? He started as the first sales hire at TripActions when the company was small and he helped scale the business to 5,000 customers, 1,200 employees and a $5 billion private valuation. Read on for Michael’s insightful advice for driving faster sales cycles. Subscribe.

Scale 293

Scale Sales Hiring Enterprise Sales 293

The Angel VC

APRIL 1, 2017

I couldn’t agree more, and I think startups should make that hire sooner rather than later. If you can hire only one or two handful of people with your seed round, hiring anybody who doesn’t either code or sell is hard to justify. Let’s say you want to hire 10 people in the next 12 months. Here’s why.

Sales Hiring 168

Sales Hiring Sales Recruiting Startup Software Review 168

SaaStr

FEBRUARY 8, 2022

Scaling a sales organization isn’t easy. Knowing which metrics matter and how to analyze them to increase your revenue and hit organizational sales goals is essential. . What makes a sales organization grow? What’s the best way to grow a sales organization? Are you compensating your teams to sell recurring revenue?

Scale 291

Scale Sales Hiring Compensation Sales 291

SaaStr

NOVEMBER 24, 2021

The SaaS sales model seems so well-established, as hundreds of founders build their businesses and raise funding. Mark Roberge, Founder of Stage 2 Capital and Senior Lecturer at Harvard Business School, shares insights from his years of experience into common SaaS sales missteps and how you can avoid them.

Sales Hiring 254

Sales Hiring Scale Compensation Sales 254

SaaStr

MARCH 5, 2021

Flock Safety’s Founder and CEO, Garrett Langley, and its VP of Growth, Alex Latraverse, know a bit about sales. Enough to go from 0 to 100 sales reps in about 18 months — and they’re looking to be well beyond 100 by the end of this month. The three things that led to ramping up sales at Flock Safety were: Achieving product-market fit.

Sales Recruiting 234

Sales Recruiting Sales Hiring Scale Sales 234

SaaStr

FEBRUARY 23, 2021

I want to spend a few posts and some time on sales comp plans for early-ish stage SaaS companies (up to say $20m in ARR). Because almost all the sales comp plans you are going to read about, and learn about are great — for SaaS companies that are well post-Scale. That work great for Salesforce, or Box. Just the top rep.

Sales Hiring 326

Sales Hiring Scale Sales Business Model 326

SaaStr

APRIL 30, 2024

How do you build GTM efficiency in SMB sales? Lesson #1: Just Say No Once he joined, Kyle quickly discovered that Owner had a leaky bucket and had either bad or no targeting on prospects, was closing a lot of poor-fit customers, and there were a lot of miss set expectations from sales so customer handoff was sketchy at best.

Scale 300

Scale SMB Sales Hiring Sales 300

SaaStr

OCTOBER 3, 2022

Imagine a coverage model, from end to end, for the full customer life cycle: from demand generation to sales to post-sales. Sales Cycle. This includes everything from inside sales to account executives to strategic asset allocation. Post Sales. Hire those who have proven their value. Land the account.

Scale 272

Scale Sales Hiring Sales Recruiting Scaling 272

SaaStr

APRIL 9, 2022

Hiring has never been easy in SaaS. Transparent compensation information is concern #1. Second, many of us worry about being fully transparent with compensation. It’s time to get over it. Second, many of us worry about being fully transparent with compensation. It’s always been hard. Fix this today.

Revenue 301

Revenue Sales Hiring Compensation Startup 301

SaaStr

AUGUST 25, 2023

Dear SaaStr: As An Employee, As an acquired employee, How Do I Negotiate My Compensation in an Acquisition? They pretty much never get any really incentives to stay, maybe some standard stock options as new hires. and in some sad cases, sales and marketing — the acquirer doesn’t even want.

Compensation 183

Compensation Acquisition Sales Hiring Finance 183

SaaStr

SEPTEMBER 12, 2023

You Have to Train Sales Reps 3–10. You have to start formal sales training by rep #3. Hire Early. Customer success teams are critical for SaaS companies as they own the customer relationship from start to finish, managing up to 75% of revenue through renewals and upsells. And you can start very small. Or they fail.

Sales Hiring 283

Sales Hiring Technical Advisors Compensation Outsourced Development 283

SaaStr

SEPTEMBER 9, 2022

Back in the day, premium comp for some software sales execs made simple and easy sense. Traditional software had 90% gross margins, and the classic enterprise sales reps, the best ones, could close a million or more dollars a year. Sales reps in low NRR and high churn environments got paid almost the same as enterprise reps.

Scale 345

Scale Venture Capital Sales Hiring Sales 345

SaaStr

NOVEMBER 30, 2023

Go-to-Market matters because sales and marketing spend remain the biggest proportion of SaaS spend, so honing in on that spend to build an engine and drive growth is paramount. Because founder-led sales worked really well for most of the early stages, but you eventually start running out of juice around $15M ARR.

Scale 274

Scale Sales Hiring Scaling Outsourced Development 274

Tom Tunguz

MARCH 27, 2025

As startups scale, effective sales implementation becomes the difference between stagnation and sustainable growth. After analyzing hundreds of sales organizations across startups, I’ve distilled the key pieces of advice that founders and leaders should keep in mind.

Scale 182

Scale Sales Hiring Startup Sales 182

Tom Tunguz

MAY 2, 2013

To many entrepreneurs, hiring the first salesperson is a mystery. The great part about sales teams and sales departments is that they quantitative - sales teams thrive on numbers. At the most fundamental level, sales productivity has to exceed costs. The output of that salesperson - sales productivity.

Sales Hiring 113

Sales Hiring Compensation Forecasting Pricing 113

SaaStr

OCTOBER 19, 2023

One thing I have learned, though: If the founders are the highest compensated people in the start-up, especially pre-Scale (e.g., pre $10m ARR) … IMHE, something is wrong.

Scale 293

Scale Sales Hiring Compensation Marketing 293