SaaStr

MAY 27, 2021

For the past 10 years, I’ve been a sales advisor for the portfolio companies of early stage venture capital firm True Ventures. It’s fascinating work for a sales mind like mine that’s focused on helping brilliant people turn ideas into revenue-driving businesses. . In his piece, Jason recommends hiring VPs in a certain order.

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Sales Hiring Scale Venture Capital Sales 240

SaaStr

MARCH 4, 2021

But, I know many of you have never hired a head of marketing before. And if you hire the wrong type — the more common type — then instead of more customers, you may end up with just a bunch of Blue Pens with your logo on them. And both types of marketers are exactly the wrong hire for you. That hire fails.

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Sales Hiring Scale Marketing Branding 357

TechEmpower SaaS

DECEMBER 11, 2023

million software developers worldwide. While the appearance matters, remember you are hiring the development firm primarily for its development skills, not its graphic design skills. Is there a project manager? An account manager? While beneficial, some project managers hinder effective communication.

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Software Development Development Software Review Software 443

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.

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Sales Hiring Marketing Technical Review Underperforming Technical Team 195

SaaStr

JULY 11, 2024

How Do You Sift Out the Bitter and Broken Individuals When Hiring? If it’s a role you’ve never hired, find someone great at it and have them do your final interview. For sales, product, or customer success, the best question you could ask is, “What would you do your first couple of weeks?” Don’t hire those people to lead.

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Sales Hiring Scale Marketing Interviewing 279

SaaStr

DECEMBER 18, 2024

Dear SaaStr: What is the best way to deal with an “unauthorized signer” on a contract in SaaS sales? A large company signed a contract to buy about $30K worth of software from us, and then the person who signed the contract said he didn’t have the authority to. I’ve been there, on both sides of it.

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Outsourcing Services Sales Hiring Software Sales 258

SaaStr

FEBRUARY 24, 2022

I’ve recently had several different conversations with founders looking to hire “PLG experts”. One wanted to hire “Mr/Ms PLG” to make their product more viral. It’s too early in this PLG cycle to hire a “VP of PLG”. Instead: * Hire a great VP of Product with strong freemium experience. Probably in that order.

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Sales Hiring Scale SMB Acquisition 268

SaaStr

JULY 14, 2024

Hiring and Interviewing Tips: Jason emphasizes the importance of interviewing at least 30 candidates for a role and consulting with an expert in the field to interview the final candidate. Product-Led Growth (PLG) vs. Enterprise Sales: Jason discusses the evolution of PLG, noting that it’s essentially freemium with better analytics.

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Sales Hiring Outsourcing Services Scale Interviewing 251

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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Sales Hiring Sales Recruiting Scale Sales 240

SaaStr

AUGUST 12, 2024

Probably the biggest challenge in vertical SaaS I see is scaling the sales team. It’s pretty easy to hire SaaS sales execs to sell … a SaaS sales product. But who do you hire to sell a very complex piece of vertical software? It’s tempting to hire consultants in an industry to do sales for you.

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Sales Hiring Scale Sales SaaS 311

Tom Tunguz

SEPTEMBER 10, 2024

Mark Roberge published The Sales Acceleration Formula about Hubspot’s journey. Account executive to SDR ratios, sales cycle lengths, conversion rates, customer acquisition costs, customer lifetime values, net dollar retention. The new software GTM playbook has yet to be written.

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Software Sales Hiring Customer Lifetime Value Scale 293

SaaStr

AUGUST 26, 2022

As SaaStr Europa 2022 drew to a close, attendees took one more opportunity to ask Jason questions about topics like how to navigate the current market, the future of work, playing in a crowded space, and hiring your first VP of Sales. It was funny for Henry to say he segmented his sales team at 80 million in ARR. Transcript.

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Sales Hiring Scale Sales Recruiting Scaling 246

SaaStr

FEBRUARY 5, 2021

Would you still hire them if they hadn't last worked at [insert logo here]? You’ll be very tempted to hire someone with a seemingly magical rolodex. You’ll be very tempted to hire someone with a seemingly magical rolodex. But at $250k a year, those two ringer deals can more than justify the hire. See who does better.

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Sales Hiring Sales Enterprise Pricing 328

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.

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Sales Hiring Sales Forecasting Travel 334

SaaStr

NOVEMBER 6, 2021

The other day Brendon Cassidy, the first head of sales at LinkedIn and the first VP of Sales at $10B Talkdesk, Adobe Sign / EchoSign, and more — and now co-CEO of Cosell — and I caught on what’s changing in the Sales Playbook for 2022. An interim VP of Sales can work — if it’s done right.

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Scale Sales Hiring Sales SMB 339

Tom Tunguz

OCTOBER 29, 2022

We can examine the sales efficiency of public software companies to get a sense. Since 2016, the average public software witnessed its sales efficiency winnowed from 52% to 47%, a decline of about 10%. Covid, marked in the orange rectangle, didn’t impact sales efficiency initially. Hiring stopped.

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Sales Hiring Sales Startup Acquisition 306

SaaStr

FEBRUARY 12, 2024

And business software spend is set to cross $1 Trillion this year for the first time ever! And so many of you in fact are, well … hiring. Most of you are, in fact: According to our latest unscientific but directionally correct survey of over 2,000 SaaS execs, 64% of you are growing your sales team in 2024. Slow it down.

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Sales Hiring Scale Sales Interviewing 311

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?

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Sales Recruiting Sales Hiring Scale Sales 331

SaaStr

APRIL 7, 2025

I’m shocked we don’t already have this for sales calls. By the end of the year, every single sales call should have a digital representative that can fill in when the human doesn’t know an answer. This will utterly change how we do sales. The Software Layer Around It Probably Is, However.

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AI B2B ChatGPT Scale 207

SaaStr

FEBRUARY 18, 2022

Sales-driven SaaS startups end up with about half their headcount in sales and marketing. Software itself and other departments get leverage. Sales doesn't. 2x the sales headcount you thought you did to hit the full plan for this year, and Q1 of next year. And start hiring all of them now.

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Scale Sales Hiring Scaling Headcount 351

SaaStr

MAY 28, 2024

If you’ve read SaaStr or have been around for the last decade, you might be familiar with some of the repeated GTM mistakes founders tend to make, but the world of hiring, people, scaling, and workplace expectations are significantly different today than they were before March 2020. Don’t make the hire. They weren’t getting any leads.

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Sales Hiring Scale AI Search AI 299

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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Sales Hiring Sales Recruiting Startup Sales 294

SaaStr

JANUARY 12, 2024

We just wrote up how some of the biggest changes of SaaS are now coming, specifically in Customer Success and Sales. Even if this is stressful for folks, as leaders and founders, you need to pause and look at this, dial it in, build better software, and make customers happy. In the bubble, people gorged on software and entitlements.

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Sales Hiring Customer Success Scale AI 315

SaaStr

JANUARY 22, 2021

As you try to hire up for your SaaS company, you’re going to be faced with a lot of choices and trade-offs. No hire is the perfect package. A certain way, even, that you build software. Customers will expect more services, more account management, more configuration. You can spend more time with prospects.

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Fractional VPE Sales Hiring Part-Time VPE Engineering 269

SaaStr

NOVEMBER 20, 2024

GitHub, founded in 2008, is a leading platform for software development and version control that has made waves since 2018 with its AI Copilot. Other Learnings in the GTM Journey GitHub has had to adjust to new sales stages and new buyer personas. You might have to take a new approach to feedback to keep up with demand.

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Scale AI Scaling Marketing 258

SaaStr

JANUARY 19, 2023

So the other day Colin Cadmus, who was VP of Sales at Aircall, summarized a career question I’ve thought about many times over the past 10+ years. If you are a great AE, a great sales exec … I know you might want “more” … but is it really better to be a VP of Sales? VP of Sales is a tough job.

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Sales Hiring Sales Startup Leadership 278

Tom Tunguz

FEBRUARY 8, 2022

The business builds software to help other crypto companies grow. Perhaps you’ll sell infrastructure to help other startups scale or software to manage internal operations. The customer roster brims with the best names, each client increases their spend every year, and the sales team outpaces its quota handsomely.

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Payment Solutions Outsourced Development Software Review Software 261

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.

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Scale Sales Hiring Sales Recruiting AI 278

SaaStr

AUGUST 13, 2024

1: Don’t hire a VP (or anyone in the early days) that you aren’t 95% sure is great. Founders between a million and $250M are talking about lowering the bar for hiring because they aren’t sure if the person is great or they’re trying to fill a gap. A great Head of Sales will move the needle. It never works.

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Sales Hiring Part-Time VPE Venture Capital Fractional VPE 300

SaaStr

APRIL 20, 2022

This famous quote from self-help author Robert Collier applies to every sales organization because excellent results come through repeatable activities, not one-off wins. Alice Katwan , SVP at Twilio , discusses how you can build a high-retention sales team while being remote. Implement systems to attract great talent.

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Sales Hiring Scale Retention Sales 267

SaaStr

MARCH 24, 2021

If you want to hire your first sales rep and close more deals, you need to understand how the sales process works, what tools your team needs to be successful and learn to speak sales. Sales definitions you should know. CRM objects — Represent the sales relationship you have with a specific person or company.

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Sales Hiring Startup Sales Outsourced Development 312

TechEmpower SaaS

MARCH 4, 2024

Key Functions with High Impact Generative AI is revolutionizing sales by enabling dynamic pricing and personalized customer interactions, boosting conversion rates and customer satisfaction. Post-sale, AI analyzes customer data to improve service and loyalty, making it a cornerstone of modern sales methodologies.

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Generative AI CTO Hire AI Sales Recruiting 443

SaaStr

MAY 5, 2022

What are some of the foundational ways sales leaders can think about building their sales teams as their company continues to expand and grow? There’s no shortage of ways to tackle this challenge, but one thing is clear: build sales teams thoughtfully and intentionally. Principle #1: Ownership is Key.

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Scale Sales Hiring Scaling Sales 246

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. Then I say … you probably made a mis-hire. They often melt. Be present.

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Scale Sales Hiring Sales Recruiting Sales 285

SaaStr

JULY 24, 2024

Sign #2: You’re Too Slow to Hire VPs If you want to gauge momentum in a startup, see how quickly they hire VPs. Is it easy to hire mercenary VPs when you’re growing 500%, or you’ve raised $100M? They both seem cool, yet only one can push out 50% more software a quarter. If you don’t see it, it’s a bad sign.

Sales Hiring 294

Sales Hiring Startup Scale SMB 294

Tom Tunguz

JUNE 20, 2020

The median startup with between 1-5M in ARR will have 12 engineers, 6 in sales and 3 in marketing. Meanwhile, the size of the marketing team increases only by 4X, compared to a 10X increase in sales and a 5X+ in engineering. As a company skills to between 1-5M in ARR, the typical company hires their first VP in Sales.

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Scale Scaling Sales Hiring Software Review 363

Tom Tunguz

MAY 2, 2022

When I asked him what he meant, he replied because capital was so plentiful and accessible today, he hired more expensive people, spent more time developing a product, and invested with a longer time horizon before demonstrating evidence of success. Software startups would need at least $1m in ARR to raise capital to muster a small round.

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Product Marketing Sales Hiring Marketing Software Development 359