SaaStr

SEPTEMBER 27, 2021

In the “old” days, there was a rough rule that as soon as you are bringing on more than 1–2 reps a quarter, you needed to hire a director of sales ops. That at that point, at a minimum, there would be too much administrative work for your VP of Sales to handle it herself. You want the sales ops help scaled up and helping before then.

Sales Hiring 289

Sales Hiring Sales Recruiting Scale Sales 289

SaaStr

AUGUST 9, 2022

Investments I've made that didn't work out: – Momentum investment – CEO a bit of bulls**t artist – CEO good at sales but weak product team / CTO. Investments I've made that had so-so outcomes: – CEO not better than me – CEO couldn't control burn rate – Not really SaaS.

Investment 307

Investment Sales Recruiting CTO Startup 307

SaaStr

JUNE 20, 2025

billion valuation after 175M round Scale AI : $29 billion valuation / “sale” with Meta’s $14.3 The Investment Reality Check Where the Smart Money is Moving AI Startup Investment Patterns: Over 70,000 AI-centric companies globally, with 25% based in the U.S. billion in funding xAI : $6.4 Palantir was ready.

AI Search 265

AI Search Artificial Intelligence AI CTO Hire 265

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. I was a local sales manager or regional manager.

Sales Recruiting 321

Sales Recruiting Sales Hiring Scale Sales 321

SaaStr

FEBRUARY 25, 2025

In addition, this year Mayfield is sponsoring our VC AI Pitch Stage and will invest from $500k-$5m in the winner! Finding and recruiting top talent is consistently ranked as one of the biggest challenges for growing SaaS companies. Meet and Find Your Next VP / CXO!

Sales Recruiting 169

Sales Recruiting Scale CTO Hire Sales Hiring 169

SaaStr

NOVEMBER 2, 2023

So we’ve spent a ton of time over the years on SaaS talking about hiring a great VP of Sales. Not only because it really matters, but because hiring the wrong VP of Sales can set you back a year — or longer. They never invest the time after they start, either. 50% of what a VP of Sales really does is recruiting.

Sales Hiring 301

Sales Hiring Sales Recruiting Sales Interviewing 301

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 236

Sales Recruiting Sales Hiring Scale Sales 236

SaaStr

MARCH 18, 2025

The result was a 5x increase over initial projections – growing from an $8M revenue target to $40M actual results – driven by a belief that market demand justified the investment. This approach required immense trust from the CEO to invest millions ahead of proven results.

Scale 174

Scale Sales Hiring Scaling Headcount 174

SaaStr

JULY 20, 2024

Dedicated Slack Channel For Every Metric From the early days at Secureframe, they have had a dedicated Slack channel for every metric: every net new sale, every expansion, every churn, and every expense. Invest in People You want to keep the bar high on talent, especially in hypergrowth, and not just in the early stages.

Sales Recruiting 298

Sales Recruiting Sales Hiring Scale Engineering 298

SaaStr

JULY 21, 2020

Your investors and others will learn a lot more hearing about sales from your VP of Sales, your CTO co-founder … and not you. This also will make you appear to be a much stronger manager. Especially, don’t try to talk over your weakest VPs and managers. Just assume none of your investors invest again.

Sales Recruiting 363

Sales Recruiting New CTO Scale CTO 363

SaaStr

SEPTEMBER 20, 2024

What are the top 10 mistakes founders are still making today when hiring their VP of Sales? In this post, we’ll delve into the common pitfalls founders encounter when hiring a VP of Sales. 1: You Can’t Stay Founder-Led Sales Forever. . #1: 1: You Can’t Stay Founder-Led Sales Forever. This one is newer.

Sales Hiring 303

Sales Hiring Sales Recruiting Scale Technical Review 303

SaaStr

AUGUST 30, 2022

On the investing side of life, the toughest meeting of all for me at least is probably the Right Co-Founder, Wrong CEO start-up. But after that, it starts to break down when you have to recruit a true management team, and in many cases, additional capital. They’ll know … Who can best recruit a management team?

Sales Recruiting 274

Sales Recruiting Technical Cofounder Scale Investment 274

SaaStr

FEBRUARY 16, 2025

While competitors invested in huge sales teams, Atlassian actually restricted direct customer interaction. The “Reverse Channel” Effect Counterintuitive channel finding: Unlike traditional partner programs that start with recruitment, Atlassian let partners self-select by becoming power users first.

Sales Recruiting 197

Sales Recruiting Marketplace as a Service Underperforming Technical Team Scale 197

SaaStr

MAY 6, 2021

A CRO owns and directs the strategy over a company’s revenue cycle, but there’s not a set standard for operational or management decisions: in addition to sales and sales development, they might be responsible for customer success, lead generation and pipelines, and even marketing and brand development. Is a CRO right for you?

Sales Hiring 299

Sales Hiring Sales Recruiting Interviewing Revenue 299

SaaStr

MARCH 7, 2021

I thought it would be worth drilling down deeper into each of them, and sharing the learnings and mistakes: 1/ Spending less time fixing things, more time recruiting senior folks to own them. No one spends enough time recruiting as it is, after $1m ARR or so. Yes, you can manage the sales team yourself. You can do this.

Part-Time VPE 293

Part-Time VPE Sales Recruiting Sales Hiring Scale 293

SaaStr

JUNE 21, 2023

They hired their first VP of Sales with a wonderful pedigree and experience at some of the hottest startups. because they needed to rebuild the sales team. They rebuilt the sales team and closed some big deals. VCs can be fickle about what they fund, but if you have revenue, you have more leeway for when you take an investment.

Sales Recruiting 293

Sales Recruiting Sales Hiring Underperforming Technical Team Pricing 293

SaaStr

MAY 1, 2021

Who can help me find that first VP of Sales? A lot of folks will want to invest in the next round of their startups. This does help with recruiting and partnerships. Many employees really do want to join one they see a well-regarded and popular VC has invested in. Let’s say a VC invests $3m into your start-up.

Sales Recruiting 313

Sales Recruiting Venture Capital Sales Hiring Startup 313

SaaStr

MAY 21, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: SaaS Capital: Across 1,500 SaaS Startups, Yearly Contracts Don’t Actually Increase NRR Dear SaaStr: How Long Should a CEO Continue Being the Head of Product? Co-Founder & Co-CEO Brendon Cassidy  2.

Sales Recruiting 246

Sales Recruiting Startup Investment SaaS 246

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. Turning over a sales team is very hard on the organization. A great VP of Sales is worth her weight in gold.

Sales Hiring 363

Sales Hiring Scale Sales Recruiting Compensation 363

SaaStr

AUGUST 8, 2023

So there’s a sort of org chart you’ll probably end up with at least twice as you start scaling in SaaS: The “Headless” Sales Org. It’s a bunch of sales reps without anyone to manage them other than … you. But if you end up not hiring a VP of Sales at that perfect moment in time (and most don’t), you’ll end up headless.

Sales Hiring 246

Sales Hiring Sales Recruiting Scale Sales 246

SaaStr

OCTOBER 5, 2020

There’s a common thinking that sales teams should be relatively high churn. That the bottom 15-20% of the sales team almost has to churn each year, because it’s survival of the fittest. At Salesforce, at Box, the bottom end of the sales team churns out each year. First, do sales reps really compete with each other?

Scale 293

Scale Sales Hiring Sales Recruiting Sales 293

SaaStr

JULY 18, 2023

The most successful entrepreneurs I’ve invested in (6+ unicorns, 3 billion+ exits) are very different in many ways. Some engineers by training, others in sales or product originally. But a few uniting characteristics of the very best: Relentless Recruiters. You have to be constantly recruiting the best. No Excuses.

Sales Recruiting 246

Sales Recruiting Scale Scaling Engineering 246

SaaStr

OCTOBER 25, 2023

For part one of this Ask Me Anything session, Jason covers everything you need to know about hiring your first VP of Sales, what he really thinks about AI, what the future of lead generation in 2024 looks like, and much more. Lead generation tools do change, but the basic motions of sales and marketing haven’t changed much.

Scale 284

Scale Sales Hiring Sales Recruiting AI 284

SaaStr

JUNE 17, 2023

The toughest part in the end is always recruiting. Recruiting. Over time, that’s recruiting more and more senior folks, so the target changes. You’ll have to be recruiting new ones all the time. That means you are constantly recruiting. Dear SaaStr: How Should I Design My First Sales Rep Compensation Plan?

Sales Recruiting 237

Sales Recruiting Scale Compensation Business Model 237

SaaStr

MARCH 22, 2022

I really appreciate you coming to talk about how to attract, hire, and build a more diverse sales team in your organization. So I’ve been building top-producing sales teams for a really, really long time. So over the years, I’ve watched many sales leaders go out and say, “Brian’s my top producer.

Sales Hiring 261

Sales Hiring Sales Recruiting Scale Sales 261

SaaStr

JULY 11, 2020

When I catch up with founders on the march from $1m to $10m in ARR, the number one topic has always shifted to recruiting. Where do i find a great VP of Sales, Marketing, Engineering, Product, Customer Success, etc.? Some times, it seems like simply building a management team is all you have time for. jasonlk) July 10, 2020.

Sales Recruiting 363

Sales Recruiting Management Engineering Customer Success 363

SaaStr

JANUARY 25, 2021

And then, I would have invested more wisely in Year 1 especially. Not Hiring 2-3 Sales Reps to Start. More on that here: When You Hire Your First Sales Rep — Just Make Sure You Hire Two. I should have invested a little more in sales reps, more quickly, one we had some initial traction (see above).

Sales Recruiting 274

Sales Recruiting Sales Hiring Scale SaaS 274

SaaStr

JULY 29, 2021

Someone great at something core you aren’t: Sales, Engineering, Marketing. Great at sales. If you hire someone to do the first sales, you’ll never understand it yourself. When you go to hire your first sales rep, hire 2. 50% of the job for a VP is recruiting. A bit more here. Great at engineering. More here.

Sales Hiring 313

Sales Hiring Sales Recruiting Interviewing Engineering 313

SaaStr

JUNE 2, 2023

Recruit diverse leaders The goal of hiring a revenue leader is to put gasoline on finding product market fit success. So the playbook for Colin during that time was tuned to one goal: hire and scale a sales team that could listen to those customers and put together a value proposition with a complimentary tone that customers were reacting to.

Sales Recruiting 261

Sales Recruiting Sales Hiring Scale Branding 261

SaaStr

NOVEMBER 19, 2020

Enough to invest, but not enough to go crazy with. More on that here and a great video discussion below: You’ll probably be ready for your first VP of Sales by $1m in ARR. Ideally, have your VP of Sales on board in time to hire reps 3-300. You’ll need a VP of Engineering by $8m-$10m ARR. ARR VPS: $1-$1.5m

Part-Time VPE 363

Part-Time VPE Sales Hiring CTO Hire Scale 363

SaaStr

JANUARY 18, 2023

It’s the most common objection you’ll get in SaaS sales … Not Right Now. It can’t strategically improve sales software, financial software, quoting software, recruiting software, QA processes, call center software, etc. And when you hire a real, great VP of Sales. Truly qualified leads and prospects. I Don’t Have Budget.

Sales Recruiting 312

Sales Recruiting Sales Hiring Technical Review Software Review 312

SaaStr

SEPTEMBER 6, 2022

Think about it — who else is so invested in your long-term success? If they’ve bought 7%, 10%, 20% of your company (with no exit on the horizon) … they’re pretty invested personally. They have a good incentive to recruit almost as hard as you do, and network a lot to help you. Your VCs are. More Money.

Sales Hiring 286

Sales Hiring Sales Recruiting Investment Acquisition 286

SaaStr

DECEMBER 4, 2023

So backstage at SaaStr Annual this year, and in a number of other conversations since, I’ve had a chance to get a few quiet moments with maybe two dozen top CROs and VPs of Sales. Yes, macro issues come up, and how they have to sell to more stakeholders now, and sales cycles are longer. But the best long ago adapted.

Sales Recruiting 293

Sales Recruiting Sales Hiring Onboarding Sales 293

SaaStr

JANUARY 27, 2021

I probably will pass on investing in you if I don’t know you want money. We recently did a New New in Venture event and I asked the question of many top VCs including David Sacks, Keith Rabois, Aileen Lee and more. “Give the VP of Sales More Time” This is always terrible advice. In one sales cycle, or less.

Part-Time VPE 348

Part-Time VPE Sales Hiring Scale Sales Recruiting 348

SaaStr

NOVEMBER 12, 2022

I’ve had the privilege to invest one way or another in about 35 SaaS companies, both as a VC and as angel. They understand why they got “No”s in the early, pre-traction days, and even, in the early-ish days when they had a handful of customers but wasn’t really taking off yet (my favorite time to invest).

Scale 343

Scale Sales Recruiting Artificial Intelligence Machine Learning 343

SaaStr

DECEMBER 28, 2019

Enough with the excuses for not having hired your real VP of Sales, or that VP of Engineering, or whatever. Hire a real recruiter. Hire more sales reps in the areas where they are profitable. Invest in Your Brand and Customer Marketing. This is the one investment everyone skimps on, but always works. Not in April.

Part-Time VPE 325

Part-Time VPE Sales Hiring Scale Sales Recruiting 325

SaaStr

JANUARY 5, 2021

1% equity considered low as a startup Director of Sales? What types of due diligence are undertaken by VCs before investing in a company? I’m Head of Product and I think our CEO is actively recruiting a VP of Product. He has met Adam Neumann for only 4 minutes and decided to invest $4.4 How much does a VC make?

Software Review 293

Software Review CTO Coach Technical Review Sales Recruiting 293