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Saastr

SaaStr covers B2B software, AI agents, enterprise infrastructure, and venture outcomes through analysis of market trends, founder experiences, and startup metrics. This page collects 2,536 posts published between February 2013 and November 2026. Recent coverage focuses on AI (Horizontal), Enterprise Software and Venture Capital & Startups. Saastr publishes roughly 59 posts a month; the best of them appear in the SandHill weekly digest.

2536 posts indexed59 in the last 30 daysAI (Horizontal) · Enterprise Software · Venture Capital & Startups · Marketing & Sales TechVisit site ↗

Friday, 18 March 2022

1 piece
Outbound Always Works. If You Do It Right. And You Put In The Time.

Tuesday, 8 March 2022

1 piece
Should Your VP Sales Start Off as a Player-Coach?↗
Enterprise Software · Venture Capital & Startups

Friday, 4 March 2022

1 piece
7 Of The Biggest Mistakes First-Time Founders Make, and How Can They Be Avoided?

Friday, 25 February 2022

1 piece
After $2m in ARR — Start Specializing Your Sales Team

Monday, 7 February 2022

1 piece
Of Course Your Competitor Is Trying to Sell To, And Steal, Your Customers and Prospects

Sunday, 30 January 2022

1 piece
VPs That Can’t Hire … They Aren’t Real VPs. At Least, Not Yet.

Saturday, 22 January 2022

1 piece
7 Changes You Can Make >Today< To Grow Faster

Thursday, 20 January 2022

1 piece
Dear SaaStr: Our Sales Team Has a 7% Win Rate. Are We Failing?

Sunday, 16 January 2022

1 piece
You’ll Lose Customers. It Hurts. But Don’t Let Them Become Angry Ex-Customers.

Wednesday, 12 January 2022

1 piece
30+ Tough Learnings from Losing a Top Customer

Tuesday, 14 December 2021

1 piece
12 Things You’ll Look Back On in B2B … And Regret

Monday, 13 December 2021

1 piece
6 Key Signs a VP of Sales Can’t Scale Beyond $5m-$10m ARR

Saturday, 13 November 2021

1 piece
The Pros and Cons of Working Directly for the CEO

Tuesday, 24 August 2021

1 piece
10 Marketing Tactics That Always Work for Early-Stage SaaS StartUps

Friday, 6 August 2021

1 piece
10 Ways to Build a Moat in SaaS. But AI is Also Making Them Weaker.

Monday, 26 July 2021

1 piece
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started?

Friday, 23 July 2021

1 piece
At Least 20% of Your New Customers Should Come from Referrals and Word of Mouth. Ideally, 50%.

Monday, 5 July 2021

1 piece
Dear SaaStr: How Do I Know If It’s The Right Time to Sell My Company?

Tuesday, 22 June 2021

1 piece
Dear SaaStr: How Do I Pay My Sales Reps on Monthly Deals?

Wednesday, 26 May 2021

1 piece
3 Things That Are Hard to Recover From. And 3 Tough Things You Bounce Back From Stronger.

Sunday, 23 May 2021

1 piece
Eventually … Almost Everyone Has a Sales Team

Monday, 17 May 2021

1 piece
12 of the Most Common Mistakes Scaling Your First Sales Team

Tuesday, 4 May 2021

1 piece
10 Things That Tell a VC You May Not Be Ready for “Prime Time”

Sunday, 2 May 2021

1 piece
Events Work. Events Are Back. But Are They Worth the Big Expense?

Saturday, 27 March 2021

1 piece
The Confounding Logic of Discounting

Friday, 26 March 2021

1 piece
Why Mergers & Acquisitions Are Weird and Unpredictable

Sunday, 7 March 2021

1 piece
10 Things That Would Have Helped Me Go From $1m to $10m Faster with Less Stress

Thursday, 4 March 2021

1 piece
Hire the Right Type of VP Marketing — Or You’ll Just End Up With a Bunch of Blue Pens with Your Logo On Them (Updated)

Monday, 1 March 2021

1 piece
No, Free Pilots and Free Trials Aren’t Revenue. Keep it Simple — And Real.

Thursday, 25 February 2021

1 piece
Should You Pay Reps More For Deals They Hunt Themselves? Sometimes. Here’s When.

Saturday, 13 February 2021

1 piece
What to Do If Your Business Decelerates

Thursday, 11 February 2021

1 piece
Got 100 Customers? Believe It Or Not, It’s Time for Your First User Conference

Wednesday, 10 February 2021

1 piece
In The Early Days, You Won’t Have Enough Customers. But Your Mini-Brand Will Come to Your Rescue.

Saturday, 30 January 2021

1 piece
I Hired My VP of Marketing at $20k MRR. It Wasn’t a Week Too Early.↗
Enterprise Software · Venture Capital & Startups

Thursday, 21 January 2021

1 piece
Why It May Take You 12-18 Months to Hire a Great VP, Sales — Period. And What to Do About It.↗
Venture Capital & Startups

Tuesday, 15 December 2020

1 piece
Sometimes All Your Bigger Customers Want is Just To Be Heard

Monday, 14 December 2020

1 piece
9 Tips To Closing More Bigger Deals

Thursday, 5 November 2020

1 piece
The Best Sales Reps Get Customers to Buy. Even When They Don’t Need to Right Now.

Thursday, 17 September 2020

1 piece
That Super-Successful VP of Sales. Great? Or Just Lucky?

Monday, 14 September 2020

1 piece
What’s Your Loss Rate? You Really Should Know
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