SaaStr

JANUARY 30, 2021

One of the starkest differences I see between First Timers in SaaS and Second Timers is when they hire their VP of Marketing. They often hire a VP of Demand Gen Marketing even before they have their first paying customers. It’s not quite as terrible as waiting too long for a VP of Sales. Second Timers know.

Sales Hiring 350

Sales Hiring Sales Recruiting Scale Marketing 350

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. So many VPs of Sales disagree with me here — at least at first when I make the point. Sales is hard.

Sales Hiring 220

Sales Hiring Sales Recruiting Sales Interviewing 220

SaaStr

DECEMBER 1, 2023

Hiring a VP of Sales isn’t new, but the conversations have evolved as the world has. Jason has written about the cheat codes for hiring VPs of Sales since 2012 and realized it was worth a deeper dive. Jason has written about the cheat codes for hiring VPs of Sales since 2012 and realized it was worth a deeper dive.

Sales Hiring 148

Sales Hiring Sales Recruiting Sales Interviewing 148

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 238

Sales Hiring Sales Recruiting Scale Outbound Sales Team 238

SaaStr

MARCH 1, 2024

In SaaS, once you have even a few million in ARR, the #1 challenge is recruiting top-tier VPs and building a truly top-tier management team: SaaS products mostly don’t sell themselves. You can hack managing and finding 1–3 reps yourself, but after that, you really need a VP of Sales. Marketing is also an art and science.

Scale 240

Scale Part-Time VPE CTO Hire Fractional VPE 240

SaaStr

JUNE 15, 2023

Dear SaaStr: Is a Big Market Really Better than a Niche Market? A big market is better than a small / niche market. Small markets are often, though not always, less crowded. If that’s the case, sometimes starting there and then expanding into a larger market segment can work out well. What Should I Expect?

Sales Recruiting 198

Sales Recruiting Marketing Sales Hiring Market Segmentation 198

SaaStr

JULY 27, 2021

Q: What are the most common challenges of a VP of marketing transitioning into a Chief Revenue officer CRO role? Way, way too many senior marketers think CRO is “the next step” for them. But here’s what happens: They don’t know how to recruit an A+ sales team. Recruiting 4, 5, 20, 50 great AEs is not the same at all.

Sales Recruiting 295

Sales Recruiting Trends Sales Hiring Growth Marketing 295

SaaStr

NOVEMBER 25, 2020

We’ve talked a lot on SaaStr about how to hire a Great VP of Sales. And we’ll keep talking about it — so long as 70% of first-time VPs of Sales don’t make it 1 year. I wanted to take a moment to explore the flip-side … a guide to why first-time VPs of Sales that finally get their shot — fail.

Sales Hiring 342

Sales Hiring Sales Recruiting Sales Headcount 342

SaaStr

AUGUST 9, 2023

Not becoming a better recruiter. I recruited a great VP of Sales, a strong VP of Marketing, a great VP of Product (now COO at Gong), and a great VP of Customer Success. But I was a sequential recruiter. I should have been recruiting more great folks, more often. And most of the team was great.

Part-Time VPE 191

Part-Time VPE Sales Recruiting CTO Scale 191

SaaStr

AUGUST 14, 2020

A mistake many founders make is hiring a VP of Sales who has many strengths — but not at sales per se. A VP of Sales who is smart, polished, and worked at the right place, in a management-level position. That can talk about quota attainment and sales operations and scaling and number. you might ask.

Sales Recruiting 361

Sales Recruiting Sales Hiring Scale Sales 361

OPEXEngine

APRIL 12, 2022

Emboldened by this seeming endorsement, I dashed off what turned into a lengthy email on interviewing and recruiting, a topic about which I am passionate not because I think I am good at it but because I think I am not. Thoughts on The Recruiting Process. Remember it’s a mutual sales process. Know what you’re looking for.

Sales Recruiting 40

Sales Recruiting Sales Hiring Interviewing Finance 40

SaaStr

MAY 14, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: 15+ of The Top Sales & Marketing Mistakes SaaS Startups Make (Updated) Cloudflare: Our Top Reps Are Hitting 129% of Quota. 7 Things All Founders Should Know About Sales with Dave Kellogg: SaaStr Workshop Wednesday LIVE 2.

Sales Recruiting 189

Sales Recruiting Scale Generative AI AI 189

SaaStr

AUGUST 30, 2022

Great product, driven team, good early product-market fit, great vision. 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? Check, check, check and check. My learning?

Sales Recruiting 221

Sales Recruiting Technical Cofounder Scale Investment 221

SaaStr

AUGUST 12, 2021

Q: What are the top 3 biggest concerns in managing a first sales team? A few of the top ones: Recruiting. Top sales people want to work for a great VP of Sales. If you don’t have one, it’s very hard to attract top sales reps. All sales execs want to make a lot of money :). Paying the best ones well.

Sales Recruiting 245

Sales Recruiting Sales Hiring Sales Onboarding 245

OpenView Labs

DECEMBER 16, 2019

So if scaling your sales organization is a priority in 2020, here are the things you need to be aware of to make sure you do so successfully. Marketing and candidate experience will be table stakes. Hiring sales leaders will get harder. So giving them a reason to choose you will be essential next year.

Sales Recruiting 53

Sales Recruiting Sales Hiring Scale Trends 53

SaaStr

FEBRUARY 5, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Dear SaaStr: Is It OK to Fly First Class to Close A Big 7 Figure Deal? SaaStr 630: Sales-led vs. Product-led? SaaStr 628: Revenue Alignment: How to Pull Marketing, Sales, and Customer Success Together with Divvy CRO Sterling Snow  5.

Sales Recruiting 183

Sales Recruiting Sales Hiring Scale Venture Capital 183

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 170

Sales Recruiting Sales Hiring Scale Sales 170

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 166

Sales Recruiting Scale Compensation Business Model 166

SaaStr

JANUARY 29, 2023

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Why Now is a Great Time to Raise Seed Funding. SaaStr 628: Revenue Alignment: How to Pull Marketing, Sales, and Customer Success Together with Divvy CRO Sterling Snow  2. Even If It’s Awful for Series A-E Rounds.

Sales Recruiting 178

Sales Recruiting Sales Hiring Scale AWS 178

SaaStr

NOVEMBER 13, 2022

Check out this week’s top blog posts, podcasts, and videos: Top Blog Posts This Week: Datadog, ZoomInfo, Atlassian, AWS: Epic Growth — But Some Real Headwinds For The First Time. When You Fall Out of Product-Market Fit. 5 Interesting Learnings from Duolingo at $360,000,000 in ARR. Top Videos This Week: 1.

Sales Recruiting 213

Sales Recruiting AWS Compensation Enterprise 213

SaaStr

AUGUST 15, 2021

Are you both willing to go 18–24 months before initial product market fit? But one of you has to lead on Customers/Sales/Marketing and the other likely on Product/Engineering for it really to work. Better recruiter than you. If your co-founder is a better recruiter than you, this is an immediate upgrade.

Sales Recruiting 272

Sales Recruiting Engineering Product Marketing Marketing 272

SaaStr

NOVEMBER 22, 2021

I've never seen a great VP of Sales hide from a miss. We’ve talked a lot on SaaStr over the years about how to hire a great VP of Sales — and how to course-correct if you’ve made a miss hire. Every great VP of Sales has 1 or 2 folks that wants to follow them from their last role. Nothing gets better in 1 sales cycle.

Sales Recruiting 231

Sales Recruiting Sales Hiring Sales Marketing 231

SaaStr

JULY 12, 2021

Q: What are some common blind spots and mistakes startups make when hiring for and building out a sales team? Some of the top blind spots founders and even VPs of Sales make: #1. You hire a sales rep to sell before you can prove you can do it yourself. You hire a VP of Sales to sell before you prove you can do it yourself.

Sales Hiring 260

Sales Hiring Sales Recruiting Sales Branding 260

SaaStr

FEBRUARY 25, 2021

Ah the VP of Sales. The first post is What a Great VP of Sales Actually Does. The second post is a script for you to use (and modify as you see fit) – 10 Great Questions to Ask a VP Sales Candidate. Just so you know, there are 48 Different Types of VP Sales. Corporate Marketing). The toughest hire.

Sales Hiring 362

Sales Hiring Scale Sales Recruiting Sales 362

SaaStr

AUGUST 28, 2020

I know we’ve hit a number of these points individually before on SaaStr, but after getting asked about the top mistakes hiring your first sales team so many times over the years, I thought it would be worthwhile to assemble a Top 10 List. Yes, you may be terrible at sales. It’s sales, after all. Here’s my Top 10 list: #1.

Sales Hiring 320

Sales Hiring Sales Recruiting Scale Sales 320

SaaStr

OCTOBER 28, 2022

Conversations about the state of the SaaS market in 2022 are everywhere, and it can seem overwhelming for entrepreneurs and business leaders to make sense of everything. However, don’t this doesn’t mean that your sales teams shouldn’t bring in more revenue –– quite the opposite.

Sales Recruiting 194

Sales Recruiting Sales Hiring Leadership Interviewing 194

SaaStr

MARCH 20, 2024

They discuss Sam’s learnings at Founders Fund, what the 2024 playbook looks like, hiring and motivating sales teams, and a handful of audience questions. On the marketing side, people got ‘lazy’ under the guise of, “Let’s increase our paid online ad spend and turn that dial up and spend more.”

Sales Hiring 244

Sales Hiring Sales Recruiting Scale Headcount 244

SaaStr

OCTOBER 27, 2022

You need engineering, product in all start-ups — but in SaaS, even in the very early days, you also need sales, client success, true support, demand gen marketing, etc. Routine Sales. You gotta hire 2 great sales reps as soon as you can. This didn’t work well until I had a Great VP of Sales.

Sales Hiring 278

Sales Hiring Sales Recruiting Scale Scaling 278

FastSpring

SEPTEMBER 15, 2020

Affiliate marketing can mean different things to different people, but at its core, it refers to paid marketing that is based on trackable performance. When there is a good fit, and affiliate marketing is used effectively, it can provide a healthy boost to sales and marketing activities, but how can you tell if it is right for you?

Sales Recruiting 141

Sales Recruiting Marketing Social Media Software Review 141

SaaStr

MAY 29, 2022

So we’ve talked so much over the years on SaaStr on how to hire a great VP of Sales, the difference they’ll make, and how the level-up comes quickly. And VPs of Sales do, too. Don’t hire a VP of Sales that isn’t truly comfortable selling to your buyer persona, especially in B2D and fintech. Be careful.

Sales Hiring 244

Sales Hiring Sales Recruiting Startup Sales 244

SaaStr

APRIL 16, 2021

Own product marketing. Own customer marketing (hopefully). Support and partner with sales. And part of being a good marketer is … well, marketing yourself. Many of the top CMOs are out there are always marketing. Having a CMO that is present, that is visible, is great for recruiting and much more.

Sales Recruiting 264

Sales Recruiting Sales Hiring Branding Product Marketing 264

Buffer Resources

SEPTEMBER 11, 2023

The reality is that the best LinkedIn users are marketing machines. I've built real friendships with the best B2B marketers in the world and I’m on a text-message basis with countless founders, CEOs, VPs, and executives. They use the platform as a content distribution system, not a resume builder. Quantify your results.

Sales Recruiting 133

Sales Recruiting Sales Hiring Scale Social Media 133

SaaStr

AUGUST 26, 2020

Founder-led sales generally stops scaling around $1m-$2m ARR. A sign to hire a real sales leader. Over the years at SaaStr we’ve talked a lot about hiring a great VP of Sales, when it works, when it does, and how it moves the needle. To stick with founder-led sales longer than most folks do, i.e. past $1.5m-$2m ARR or so.

Sales Hiring 276

Sales Hiring Sales Recruiting Scale Sales 276

Neil Patel

FEBRUARY 17, 2021

With the competition for customers becoming stiffer by the day, brands have to be savvy about the way they do their marketing. You must employ marketing strategies that work. One such marketing strategy is direct response marketing. What is Direct Response Marketing? Advantages of Direct Response Marketing.

Sales Recruiting 141

Sales Recruiting Marketing Social Media Branding 141

SaaStr

FEBRUARY 26, 2021

Brendon Cassidy, my VP of Sales wrote a version of this piece a while back. I though an updated version of this would be good for founders thinking about hiring a VP of Sales … VPs of Sales themselves … and VPs-to-be to read — Jason, ed. … 10 Rules to Being a VP of Sales in a Startup.

Sales Hiring 286

Sales Hiring Sales Recruiting Startup Sales 286

SaaStr

MARCH 25, 2023

So one recent survey we did really brought out a healthy debate: does your VP of Sales really need to be a product expert? Many of the comments said it was more important a VP of Sales understand process and leadership more than the product itself. They often melt. I say, you just gotta know the product. Not just with buzzwords.

Scale 217

Scale Sales Hiring Sales Recruiting Sales 217

SaaStr

DECEMBER 10, 2020

I hear again and again from SaaS founders growing to $5m, $10m ARR or even more that they don’t need a certain VP — with the exception of a VP of Sales. That they can get away without no one in the role, or a just a junior person in marketing, in product, in success, in biz dev, etc. I Need a VP of Sales.

Sales Hiring 349

Sales Hiring CTO Hire Sales Recruiting Scale 349