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. Watch them fly.

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Sales Hiring Sales Recruiting Interviewing Startup 307

SaaStr

APRIL 12, 2021

The biggest mistake folks make when they go to hire a VP of Sales is hiring a top AE that's never really built a team. But it does not remotely prepare you to be a VP of Sales on its own. Not until you are Uipath, or Canva, or Algolia, or whatever the next super hot startup is. Everything is overheated.

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Sales Hiring Growth Hacking PayPal Startup 340

SaaStr

MARCH 23, 2025

5 Key Learnings from Scaling from 3 to 75 Go-To-Market Team Members in Less Than 12 Months The latest SaaStr CRO Confidential is out and Sam Blond did a great deep dive with Graham Mareno, VP of Worldwide Sales at Codeium. Create Compelling Economic Incentives For sales talent, compensation is critical.

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Sales Recruiting Sales Hiring Scale AI 245

SaaStr

MARCH 29, 2025

Dear SaaStr: What Are The Best Ways to Transition From The Founder-Led Sales Stage? Transitioning from founder-led sales to a commissioned sales team is one of the most criticaland trickysteps in scaling a SaaS business. Its where many startups hit roadblocks, but if you do it right, its a game-changer. Be specific.

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Scale Sales Hiring Sales Compensation 204

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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Sales Hiring Sales Recruiting Scale Technical Review 310

SaaStr

FEBRUARY 26, 2025

Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers? Theres no way a SaaS startup needs a CRO or COO or other C-level Officers Without a Clear, Single Functional Area to Own Until $40m-50m+ in ARR. A great VP of Sales who took a company from $1m to $50m may want to try CRO now.

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Sales Hiring Startup Management SaaS 212

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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Sales Hiring Sales Recruiting Sales Interviewing 308

SaaStr

SEPTEMBER 26, 2022

Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)? How can a CEO hire those C-level positions for the first time as a CEO and entrepreneur? Here are some rough rules: You want a VP of Everything (Sales, Marketing, Product, Eng) by about $5m ARR, and ideally, Sales and Marketing well before that.

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Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 291

SaaStr

APRIL 1, 2023

On the hiring side, it often seemed like you just couldn’t hire anyone. Everyone was hiring everyone, anyone, back in mid-2021. We hired job hoppers that never stayed anywhere for more than 18 months for leadership roles. The post Lowering the Hiring (And Investing) Bar Didn’t Work appeared first on SaaStr.

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Sales Hiring Investment Leadership Startup 317

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. — Jason BeKind Lemkin #???????????? jasonlk) May 23, 2022.

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Sales Hiring Sales Recruiting Interviewing Startup 324

SaaStr

JUNE 27, 2020

A little while back we put together some of the top sales & marketing mistakes SaaS companies and founders make, especially in the early days. Sales: Hiring any reps you wouldn’t buy from yourself. Later, once you have a strong VP of Sales, it’s fine though. Your sales reps need to eat. Hiring just 1 rep.

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Sales Hiring Scale Startup Marketing 363

SaaStr

FEBRUARY 22, 2022

Ok we’ve talked a bit more on SaaStr over the years on how to hire a Great VP of Sales , but hiring a Great VP of Marketing is just as important. Maybe in some ways more so, in that you can generally hire a great VP of Marketing earlier. Do you make the hire now? Not just in sales. What do I mean?

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Sales Hiring Growth Hacking B2C SMB 307

SaaStr

DECEMBER 11, 2021

We’ve talked about how all the Second Timers are hiring in customer success way early , ahead of sales, ahead of revenue. And it’s been fun to see lots of startups and bigger companies internalize this. To hire in customer success. So why make this hire so early when cash is tight? They wait too long.

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Sales Hiring Customer Success Headcount Churn 300

SaaStr

OCTOBER 7, 2020

As you scale up in SaaS, one thing I can almost guarantee is that you are going to hire some VPs who were either fired or quit their last role. Especially in Bay Area-centric startups. So you’ll end up hiring VPs who went through a significant transition at their last gig, sometimes an involuntary one. That can be great.

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Sales Hiring Scale Interviewing Startup 362

SaaStr

MAY 12, 2022

The biggest mistake you can make as a founder when you hire your first VP of Sales is stepping out of sales. It only works with the very best VPs of Sales. Every other first VP of Sales needs you doing at least half of what you were doing before. A founder hires a Pretty Good First VP of Sales.

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Sales Hiring Sales Investment Engineering 310

SaaStr

SEPTEMBER 1, 2023

Ah, hiring those first 1 or 2 sales reps. So often, they are mis-hires. But when you get that Sales Magician — they really can be a game changer. If that’s you, hiring your first few sales reps, here are our Top 10 SaaStr Posts on Hiring Your First Few Sales Reps: #1.

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Sales Hiring Scale Sales Startup 279

SaaStr

OCTOBER 1, 2022

What almost never works, somewhat surprisingly, is hiring a Director of Outbound as your first outbound hire. I see many startups want to add outbound, but not really have a lot of experience. And especially, a new VP of Sales comes in without real outbound experience. Why does this seemingly logical hire fail?

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Sales Hiring Scale Sales Startup 311

SaaStr

DECEMBER 19, 2023

Dear SaaStr: What are the signs that an enterprise SaaS startup is ready to scale by hiring more sales people? For a higher-velocity, in-bound driven SaaS product, most sales reps will have trouble processing more than 50 or so truly qualified leads a month. Before $10m ARR or so, more qualified leads = more sales.

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Sales Hiring Scale Scaling Sales 307

SaaStr

APRIL 13, 2025

Don’t try to evolve into a compound startup later – Unlike conventional wisdom about starting focused and expanding, Conrad believes it’s “really hard” to transition from a point solution to a compound startup: “You kind of have to almost refound the company.” The advantages are substantial: 1.

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Startup Sales Hiring Underperforming Technical Team Cloud 163

SaaStr

FEBRUARY 7, 2025

His view is your sales team teaches your customers how to get value out of your product. Ron explains: “Wehire mostly technical backgrounds, but as our customers get larger and larger, you start to get global account managers, and they’re going to have much more business strategic account management experience.

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Scale Sales Hiring Scaling Revenue 183

SaaStr

MARCH 17, 2025

Thats okayplenty of successful startups have been built by solo founders. Hire an Ex Post-Facto Co-Founder: This is someone who isnt technically a co-founder but acts like one. It could be a VP of Product, Sales, or Engineeringsomeone who takes ownership of a big chunk of the business and cares almost as much as you do.

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Sales Hiring Scale Scaling Engineering 251

SaaStr

JULY 11, 2024

How Do You Sift Out the Bitter and Broken Individuals When Hiring? As a startup, most people who come to an interview appear happy. If it’s a role you’ve never hired, find someone great at it and have them do your final interview. What do the best Heads of Product and VPs of Sales say? Don’t hire those people to lead.

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Sales Hiring Scale Marketing Interviewing 292

SaaStr

FEBRUARY 1, 2025

When I look at the VP of Sales / CRO that didnt work out the past 12-18 months across the SaaStr Fund portfolio and my ecosystem, one thing stands out. And its an old SaaStr theme: #1: You have to hire folks in sales where their last job was harder. There may exceptions at rocketships. You often fly. Voice APIs?

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Sales Hiring Sales compliance Interviewing 190

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. Yes, you need it at scale — but not in the same ways startups do. That hire fails.

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Sales Hiring Scale Marketing Branding 357

SaaStr

JULY 18, 2022

Q: Dear SaaStr: What Are Some Good Strategies To Hire People In The Early Days? A few basic thoughts … that many still don’t get right: Don’t hire anyone that doesn’t understand their functional area better than you do. Don’t hire anyone you don’t believe in. If you’re not sure how to hire for a role, get an advisor that does.

Sales Hiring 291

Sales Hiring Strategy Interviewing Startup 291

SaaStr

MARCH 12, 2025

With 10+ years as a CMO at companies ranging from $1M to $1B in revenue, another 10+ years as CEO of companies in the $0-$100M range, and extensive experience as an independent director on startup boards, Dave offers a 360-degree perspective on marketing’s role in SaaS success. Better to hire for your specific needs and stage.

Sales Hiring 206

Sales Hiring Marketing Technical Review Underperforming Technical Team 206

SaaStr

JANUARY 19, 2025

Dont Forget the Services Revenue Top Vids & Pods: #1: Adding AI to SaaS: Inside the AI Product Strategies of Figma, Cloudflare, GitHub and Ramp #2: HubSpot Co-Founder Brian Halligan on How to Hire Great VPs and How M&A Really Works #3: How To Perfectly Pitch Your Seed Stage Startup With Y Combinator’s Michael Seibel #4: LIVE: Top 10 Learnings (..)

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AI Sales Hiring Venture Capital Startup 280

SaaStr

JANUARY 8, 2025

It was started in 2014 when founders Daniel and Jonathan were working together at a delivery startup and experienced firsthand how slow background checks were slowing down worker onboarding. The SMB sales team was incentivized purely on logo acquisition rather than revenue. With only 4% conversion by month two versus a 10% goal.

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Revenue Scale Sales Hiring Compensation 300

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. This is a rough guide.

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Sales Hiring Scale Startup Compensation 329

SaaStr

SEPTEMBER 26, 2023

Dear SaaStr: What is The Biggest Difference Between Running a 10 Person Startup and a 100 Person Startup? The biggest structural difference is you have to hire all the VPs by employee 50–100. You have to let go of the many mistakes that will be made — so long as you hire great VPs to run the playbooks.

Sales Hiring 307

Sales Hiring Startup Scale Engineering 307

SaaStr

JULY 24, 2024

In a recent Workshop Wednesday, SaaStr Founder and CEO, Jason Lemkin sat down to discuss 9 signs a startup isn’t going to make it. So, let’s look at the nine signs a startup will likely not be a real success. Sign #2: You’re Too Slow to Hire VPs If you want to gauge momentum in a startup, see how quickly they hire VPs.

Sales Hiring 307

Sales Hiring Startup Scale SMB 307

SaaStr

NOVEMBER 9, 2023

Dear SaaStr: What are some of the “ultimate sins” in marketing and sales and success in SaaS in the early stages? My list of some bad ones: Sales: Hiring any reps you wouldn’t buy from. Later, once you have a strong VP of Sales, it’s fine though. Your sales reps need to eat. Hiring just 1 rep.

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Sales Hiring Scale Startup Marketing 290

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 263

SaaStr

JANUARY 5, 2023

Salesforce is ceding the startup CRM market to HubSpot. But I would tell every startup I invested in or worked with to move onto Salesforce — at least once they hire a real VP of Sales. I told them their VP of Sales would be used to Salesforce and pick it as their CRM, and you had to let them pick their tool of choice.

Startup 71

Startup Sales Hiring Scale Investment 71

SaaStr

APRIL 5, 2025

Kobe Conrad, Head of Growth at Rupa Health and Onleet, took the stage at SaaStr Annual to break down the five growth channels that transformed Rupa Health from a $20M seed-stage startup into a platform with hundreds of millions in equity and a 4,000% increase in user acquisition over three and a half years.

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Scale AI Search Sales Hiring Acquisition 232

SaaStr

JANUARY 26, 2025

Top Posts: #1: The Top 10 Mistakes SaaS Startups Make: The 2025 Edition #2: When You Raise Venture Capital, A Clock Starts Ticking. At First, Softly. Then Louder and Louder. #3: 3: What Works Better for Field Marketing: Small, Intimate Events? Or the Big Mega Industry Events? #4: 4: AI is the Best Thing to Ever Happen to SaaS.

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Sales Hiring Venture Capital AI Startup 227

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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Sales Recruiting Sales Hiring Scale Sales 363