SaaStr

JANUARY 24, 2023

During the Boom Times of late ’20-early ’22, we all often confused Taking Risks in hiring … with Just Plain Ignoring Flags. The best VPs of Sales I’ve hired were Directors of Sales before. That’s far better in my experience than hiring a random top tier university grad.

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SaaStr

SEPTEMBER 20, 2024

What are the top 10 mistakes founders are still making today when hiring their VP of Sales? SaaStr CEO and Founder, Jason Lemkin, has done numerous surveys now that confirm that a startling 70% of first hires don’t make it. In this post, we’ll delve into the common pitfalls founders encounter when hiring a VP of Sales.

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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. Don’t make this hire. 50% of what a VP of Sales really does is recruiting.

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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. But they have to close something in one sales cycle.

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SaaStr

JULY 13, 2023

A strong sales leader is vital to any company hoping to scale. With this in mind, hiring for the Head of Sales role is one of the most important things a business can do. Unfortunately, too many companies focus on the wrong things when hiring their sales leaders, which can lead to hires that aren’t the best fit for the business.

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SaaStr

MAY 24, 2022

So did startups. Many mediocre hires were made to fill slots, reference checks not made, etc. VCs funded startups in a day, with limited diligence, sometimes at 100x revenue for the hottest of deals. And startups … well, they moved pretty darn quickly too. A related post here: How To Get Better at Recruiting. (We

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Sales Hiring Sales Recruiting Interviewing Startup 320

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.

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SaaStr

MARCH 5, 2025

Codium is one of the fastest-growing startups in the AI coding assistant space, having scaled its go-to-market team from 3 to 75 in just under a year. Before hiring their first sales reps, the founders personally closed millions in revenue. Their strategy?

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Sales Hiring Scale Sales Recruiting AI 180

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?

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Tom Tunguz

APRIL 5, 2020

Which startup sectors are most affected by coronavirus? Roger Lee is maintaining Layoffs.fyi , which is a table of all the startups who have unfortunately cut staff. On the brighter side, it is a resource for startups looking to hire as they grow. Over the weekend, I analyzed Roger’s data to answer this question.

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SaaStr

JUNE 6, 2025

Even as the world has gone more remote and distributed, there are unique advantages to being based here—especially for startups that want to build something really big. Whether it’s hiring a VP of Sales who’s scaled a team to $50M ARR or finding a product leader who’s built enterprise-grade solutions, the talent pool here is unparalleled. #2.

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Sales Recruiting Scale Sales Hiring B2B 224

SaaStr

SEPTEMBER 10, 2021

We’ve talked a ton on SaaStr about how to hire a great VP. We even have 3 great checklists to make sure you hire right: VP of Sales hiring checklist here. VP of Marketing hiring checklist here. VP of Customer Success hiring checklist here. Those can be amazing hires. And for your stage.

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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.

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SaaStr

FEBRUARY 1, 2021

That you absolutely, positively, have to only hire “Rockstars” in your startups. If you don’t think you need a great VP of Sales, Product, Marketing, Customer Success, and Engineering — then all that all that means is you’ve never worked with a great one. Should you hire an up-and-comer?

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SaaStr

MARCH 3, 2023

At SaaStr APAC 2023, Scott Pugh, VP of Sales at Figma, shared how to scale these two sales teams while building culture. Pugh’s strategy is simple, albeit not always easy: Recruitment — how to hire the best talent to scale your sales organization. Let’s look at five tips to consider for successful recruiting.

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Scale Sales Recruiting Sales Hiring Scaling 273

Tom Tunguz

SEPTEMBER 7, 2020

When a new leader joins a startup, their impact hinges on their ability to build their teams. Whether you manage a team of engineers, a team of regional sales managers, or the company, your first responsibility is to hire and successfully manage the seven people who will form your leadership team.

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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.

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SaaStr

JUNE 20, 2025

And the evidence is mounting that AI startups aren’t just complementing SaaS — they’re actively hunting traditional SaaS incumbents for lunch. The Billion-Dollar AI Unicorn Factory The scale of AI startup funding isn’t just impressive — it’s existential for SaaS: The AI Billion-Dollar Club: OpenAI : $8.4

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Tom Tunguz

JULY 25, 2020

To handle this complexity, some startups have split the role under two leaders: a head of product marketing and a head of demand generation. But I see this company structure more frequently across SaaS startups. By hiring two focused people, the startup is free to find the best person in each role. 464k results.

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SaaStr

MARCH 24, 2020

Nothing matters but recruiting and using your personal network. Sam Blond, CSO at Brex explains why recruiting, networking and employee happiness is the key to this playbook on recruiting your sales team. Sam Blond | Chief Sales Officer @ Brex. I’m doing The Playbook To Recruiting Your Sales Team.

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Sales Recruiting Sales Hiring Scale Underperforming Technical Team 189

SaaStr

MARCH 14, 2022

We’ve talked a ton about How to Hire a Great VP of Sales on SaaStr, but I wanted to highlight a few VP of Sales “personas” that I rarely, if ever, see work out. Because again and again, many of your will hire this VP of Sales. Here are the types of VP of Sales that just never work out.

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Sales Recruiting Sales Hiring Technical Review Scale 300

Tom Tunguz

NOVEMBER 16, 2015

Mark Roberge, the Chief Revenue Officer at Hubspot, has spent 20 years in startups. 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. The first step is hiring a sales leader.

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SaaStr

JUNE 21, 2024

Sam Blond, the former CRO at Brex with 15 years in tech sales, took the stage at SaaStr Europa 2024 to share nine easy sales concepts that so many get wrong. Sam got his first job in tech sales as an SDR for Jason Lemkin’s company, EchoSign, which later sold to Adobe and launched his career. They did this right at Brex.

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SaaStr

SEPTEMBER 8, 2024

When building a list, try to define your potential customer as granularly as possible – size, location, industry, ideal buyer, sales process, technology stack, etc. This will allow you to be much more targeted with your messaging when reaching out and will help you optimize your sales funnel. Pricing is always evolving.

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Sales Recruiting Scale Venture Capital Sales Hiring 322

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.

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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.”

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Scale Sales Hiring Scaling Sales Recruiting 180

SaaStr

MAY 10, 2023

In this week’s episode of CRO Confidential, host Sam Blond, Partner at Founders Fund, continues a mini-series on founder-led sales with Colin Zima, founder and CEO of Omni. Leverage Your Network First When you’re ready to hire your first AE, don’t create a job posting and see who comes in. Instead, leverage your network.

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SaaStr

FEBRUARY 12, 2022

What was the first warning sign your VP of Sales wasn't going to work out? A new VP of Sales doesn’t always double sales in 30 days — although it can happen in SMB sales. The old playbook does help, but every great VP of Sales knows they quickly have to evolve it to any new role.

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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. Too many startups don’t train or onboard reps properly.

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SaaStr

MAY 17, 2021

Q: Dear SaaStr: What is the path to become a great VP of Sales? Each story is different, but there is one clear penultimate step: recruiting and managing a small team yourself. What 95 times out of 100 is a recipe for failure is jumping straight from successful individual rep to VP of sales. Not just managing one.

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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.

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SaaStr

SEPTEMBER 27, 2023

Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder? Many will want to quit when you finally have revenues, just not enough to hire anyone else or pay anyone a decent salary. From $1m in ARR, and Then Forever After: Recruiting Great VPs. You need to learn to become great at recruiting. It never ends.

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Sales Recruiting Sales Hiring Startup Scale 284

Tom Tunguz

AUGUST 2, 2019

If you must choose a long term headquarters for your startup, call an executive recruiter who focuses in that city. Ask her about each of the key roles your company will need to hire in the next 2 to 3 years. VP Engineering, VP Product, VP Sales, VP Customer Success, VP Marketing, or VP Operations.

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Sales Recruiting Sales Hiring Startup Scale 255

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. Work with Great Executive Recruiters ”The first time I saw an invoice for an executive search, I think I had a heart attack,” Shrav joked.

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Tom Tunguz

AUGUST 18, 2018

Startups are business machines engineered to grow quickly. This is one of the most important things to keep in mind when hiring. Every lead hired today, whether marketing , sales, engineering or product, will have a very different job nine months from now, much less two years from now. You hire a head of engineering.

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Sales Hacker

JUNE 20, 2025

People post in our Slack channel that they’re hiring but it’s not posted. And in a world of layoffs, AI disruption, and hiring freezes, your next opportunity will increasingly come through backchannels, not applications. Refresh your LinkedIn to tell a singular story Most recruiters spend less than 20 seconds on a profile.

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SaaStr

MAY 5, 2021

Did you hire a good enough VP? 4 part test: – who great did they hire in the first 60 days? Hiring your VPs as a founder is tough. How do you know, quickly, if you’ve hired a “good enough” VP? Or if you hired someone that talked the talk, but isn’t the right fit for your startup?

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Part-Time VPE Sales Hiring Sales Recruiting Metrics 239