SaaStr

OCTOBER 13, 2024

Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups? I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done. I felt part of your core job as CEO was to assemble a management team, not complain about how you couldn’t get it all done.

Sales Hiring 257

Sales Hiring CTO Hire Scale Startup 257

SaaStr

NOVEMBER 3, 2024

I’m not talking about any close friends in sales here. But — there are a ton of folks I know that used to be great in sales. The other day someone who used to be an A+ sales leader emailed me about a position I’d introduced to him as a super hot start-up. And you just might want to hire him.

Sales Hiring 278

Sales Hiring Sales Interviewing Startup 278

SaaStr

APRIL 21, 2022

Yes, sometimes it’s OK to hire a VP of Sales that everyone loves. At least 9 times out of 10, if everyone on the team loves a VP of Sales, it’s the wrong hire. And this especially matters because I often see CEOs picking between 2 final VP of Sales candidates. VCs love VP of Sales that sell up well.

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Sales Hiring Scale Sales Interviewing 350

SaaStr

JUNE 22, 2025

Dear SaaStr: I’m a Seed Stage, First Time VP of Sales. Don’t wait to hire an SDR team—start building pipeline immediately. Use tools like LinkedIn Sales Navigator, Apollo, or ZoomInfo to find leads. What’s the sales cycle? Hire Slowly, But Hire Right Don’t rush to hire a big team. Updated)

Sales Hiring 209

Sales Hiring Sales Recruiting Sales Metrics 209

SaaStr

JUNE 1, 2025

Dear SaaStr: What are the most common mistakes first-time founders make when building enterprise sales teams? The most common mistakes first-time founders make when building enterprise sales teams are surprisingly consistent. Heres the breakdown: Hiring a VP of Sales Too Early : This is a classic.

Outsourcing Services 186

Outsourcing Services Sales Hiring Scale Enterprise 186

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.

Sales Hiring 294

Sales Hiring Sales Recruiting Interviewing Startup 294

SaaStr

JUNE 26, 2025

Dear SaaStr: How Are VP of Sales Commissions Normally Structured? VP of Sales commissions in SaaS are typically structured around a 50/50 On-Target Earnings (OTE) model. Upside for Overperformance : Great VPs of Sales often expect uncapped commissions. If they exceed the targets, they should earn significantly more.

Sales Hiring 201

Sales Hiring Compensation Sales Benchmarks 201

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.

Sales Recruiting 233

Sales Recruiting Sales Hiring Scale AI 233

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 298

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.

Sales Hiring 205

Sales Hiring Startup Management SaaS 205

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 191

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.

Sales Hiring 296

Sales Hiring Sales Recruiting Sales Interviewing 296

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.

Sales Hiring 315

Sales Hiring Sales Recruiting Interviewing Startup 315

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.

Sales Hiring 306

Sales Hiring Investment Leadership Startup 306

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.

Sales Hiring 277

Sales Hiring Part-Time VPE VPCs (Virtual Private Cloud) Startup 277

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 298

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.

Sales Hiring 268

Sales Hiring Scale Sales Startup 268

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?

Sales Hiring 299

Sales Hiring Scale Sales Startup 299

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.

Sales Hiring 294

Sales Hiring Scale Scaling Sales 294

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.

Sales Hiring 244

Sales Hiring Scale Scaling Engineering 244

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.

Startup 152

Startup Sales Hiring Underperforming Technical Team Cloud 152

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 169

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 279

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.

Sales Hiring 357

Sales Hiring Scale Marketing Branding 357

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?

Sales Hiring 178

Sales Hiring Sales compliance Interviewing 178

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.

Sales Recruiting 225

Sales Recruiting Scale Sales Hiring B2B 225

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 278

Sales Hiring Strategy Interviewing Startup 278

SaaStr

APRIL 14, 2025

SaaS Capital surveyed 1,000 B2B startups of varying sizes to find out just how much today they are spending in sales and marketing in this new era of efficiency. About the same as before In fact, the median amount spent on sales is up from a year before. Its not just Marc Benioff hiring more sales execs in the AI era.

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Scale Sales Hiring B2B Startup 247

SaaStr

JUNE 14, 2025

Successful startups balance optimism with realism by presenting a compelling vision while grounding their projections in credible, data-backed assumptions. Use a Bottom-Up Approach for Projections Startups often get into trouble by pitching top-down projections, like “If we capture 1% of a $10B market, we’ll hit $100M ARR.”

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Scale Sales Hiring Benchmarks Churn 229

Kellblog

JUNE 1, 2025

When a B2B SaaS startup is hiring their first salesperson, I think they should look for someone who: Is a dyed-in-the-wool seller with sales blood coursing through their veins. Their first sales job was in high school and they’ve sold anything from dictionaries to shoes to cars early in their career. Go find one.

Sales Hiring 60

Sales Hiring Startup Scale Onboarding 60

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

AI Search 283

AI Search Artificial Intelligence AI CTO Hire 283

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 269

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 193

Sales Hiring Marketing Technical Review Underperforming Technical Team 193

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.

Sales Hiring 321

Sales Hiring Scale Startup Compensation 321

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.

Revenue 286

Revenue Scale Sales Hiring Compensation 286

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 294

Sales Hiring Startup Scale Scaling 294

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 70

Startup Sales Hiring Scale Investment 70