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Blog Posts, Career Growth & Advice, Early, Human Resources, Q&A
Dear SaaStr: What are Some Red Flags That Signal You Shouldn’t Take a Start-up Job?
Dear SaaStr: What are Some Red Flags That Signal You Shouldn’t Take a Start-up Job? A few B2B/SaaS specific thoughts. 1. Don’t join a B2B/SaaS start-up that won’t share its…
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Blog Posts, Early, Q&A, Sales
Dear SaaStr: How Do Startups Really Sell to Big Enterprises Before They’re Proven?
Dear SaaStr: How Do Startups Really Sell to Big Enterprises Before They’re Proven? You solve their problems. And you solve a specific problem that is important to your buyer —…
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Blog Posts, Exit Strategy, Growth, Q&A
Dear SaaStr: How Do I Do My Retention Negotiation in an Acquisition?
Dear SaaStr: How Do I Do My Retention Negotiation in an Acquisition? A few thoughts on retention compensation when you are acquired First, understand that the acquirer almost certainly already…
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Blog Posts, Q&A
Dear SaaStr: What Do You Look First In Your First VP of Product?
Dear SaaStr: What do you look for when hiring a VP of Product for a B2B SaaS? In particular, the dilemma I’m facing is hiring between a SaaS expert or…
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Blog Posts, Q&A
Dear SaaStr: When should a bootstrapped startup hire a (CFO, COO, CMO)?
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? What…
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Blog Posts, Early, Q&A
5 Ways to Acquire Customers Before You Have Any Budget
Q: How do you acquire customers on a zero dollar budget? You use “sweat dollars” instead: Get any press and PR you can. It doesn’t have to be TechCrunch. Get…
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Blog Posts, Exit Strategy, Growth, Q&A
Dear SaaStr: What Are SaaS Companies Generally Worth When They Are Acquired?
Figma cost $20B because (x) It was 2x the last round price (y) it wasn't for sale Lots of deals end up getting priced like that in the end —…
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Blog Posts, Q&A
Dear SaaStr: How Do You Steal Customers From the Leader in the Space?
Dear SaaStr: How Do You Steal Customers From the Leader in the Space? First, don’t hide. Don’t run away from where they are. You have to be where your competitors…
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Blog Posts, Growth, Marketing, Marketing, Q&A
Dear SaaStr: What Makes the Ideal Demand Generation Candidate for a Growth-Stage SaaS Company?
Dear SaaStr: What makes the ideal Demand Generation candidate for a growth-stage SaaS company? 90% of the candidates you meet will not have: owned a funnel revenue goal/KPI: pipeline, leads,…
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Blog Posts, Fundraising, Q&A
Dear SaaStr: How Important Are Happy Employees When VCs Invest?
Do startup investors care about how employees are treated where they invest? The reality is VCs, for the most part, sort of care. What I can tell you 100% for…
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Blog Posts, Early, Q&A
Dear SaaStr: What Are the 5 Things Every Founder Should Know In the Early Days?
Dear SaaStr: What Are the 5 Things Every Founder Should Know In the Early Days? My list: Slow it down if you don’t have a great co-founder. Another idea will…
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Blog Posts, Career Growth & Advice, Early, Leadership, Other, Q&A
Dear SaaStr: What Do You Have to Get Right in a Start-Up?
Dear SaaStr: What Do You Have to Get Right in a Start-Up? So many folks I meet want to start a start-up. They have an idea they are passionate about….
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Blog Posts, Early, Fundraising, Leadership, Q&A
7 Guidelines on Selling Some of Your Stock in a VC Round
"Secondary liquidity", where you can sell some of your shares in a round, is more and more common now Should you sell if you can? The answer to me is…
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Blog Posts, Q&A
Dear SaaStr: How Soon Do Startups Get Notified by VCs About Their Decision to Invest?
Dear SaaStr: How Soon Do Startups Get Notified by VCs About Their Decision to Invest? Pretty quickly. Once a VC really wants to invest … you’ll know. Often in just…
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Blog Posts, Q&A
Dear SaaStr: What Are the Danger Signs a Startup Isn’t Going to Work Out?
Dear SaaStr: What Are the Danger Signs a Startup Isn’t Going to Work Out? Let me share my list. It’s more about things I worry about after: Founders’ understanding of…
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Blog Posts, Career Growth & Advice, Early, Fundraising, Leadership, Q&A
Dear SaaStr: How Do Founders Take Advantage of VCs?
Q: There are a lot of examples of VCs taking advantage of entrepreneurs. What are some examples of entrepreneurs taking advantage of VCs? I can name a few. But, it…
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Blog Posts, Q&A
Dear SaaStr: How Many Investor Updates and Meetings Do I Owe My Investors?
Dear SaaStr: I am a startup founder that writes extensive monthly report to investors. We are also doing weekly meetings, are they asking for too much of my time? Yes,…
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Career Growth & Advice, Q&A
Dear SaaStr: What’s the #1 Thing That Sets Great VPs Apart From the Rest?
Dear SaaStr: What’s the #1 Thing That Sets Great VPs Apart From the Rest? The truly great VPs, They have a stream of great candidates coming through the door (or…
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Blog Posts, Q&A
Dear SaaStr: What Do VCs Offer Besides Money?
Dear SaaStr: What Do VCs Offer Besides Money? Many VCs, in the end, only offer money and advice you often don’t need (which can be worse than no advice at…
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Blog Posts, Early, Fundraising, Q&A
Dear SaaStr: What Are The Top Things to Know Before Starting a SaaS Startup?
Dear SaaStr: What Are The Top Things to Know Before Starting a SaaS Startup? Top of my list: Picking a mediocre co-founder just doesn’t work. You can’t settle here. You…
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Blog Posts, Early, Growth, Hiring, Q&A
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO?
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO? Let me take a slightly different take on the question. Maybe you are really asking – “Am…
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Blog Posts, Q&A
Dear SaaStr: When Do You Know It’s Time to Tilt a Bit in SaaS?
Dear SaaStr: When Do You Know It’s Time to Tilt a Bit in SaaS? I think in SaaS, it’s time to tilt when you have a handful of customers, and…
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Blog Posts, Career Growth & Advice, Early, Leadership, Q&A
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk?
Dear SaaStr: What Should I Do if My Co-founder is a Complete Jerk? It’s not going to work. The issue isn’t so much that he’s a complete jerk. It’s that…
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Blog Posts, Customer Success, Customer Success, Q&A
Dear SaaStr: How Do You Handle Customers Upset About an Autorenewal?
Dear SaaStr: How do you handle B2B customers who want a refund on an annual subscription because they didn’t realize that their credit card would get charged again a year…
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Early, Exit Strategy, Q&A
Dear SaaStr: Why Do Big Companies Buy Small Companies Instead of Competing?
Dear SaaStr: Why do big companies buy small companies instead of competing? Well, first of all, they often do both. They often start off competing, at least a bit. Salesforce…
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Popular Q&A
The 3 Types of Day 1 Pricing: Low End of Normal. Identical. And Anchor High.
Q: As an entrepreneur starting out, is it better to overprice your product or underprice it? I remember years ago I was at an event with the CEO of a SaaS leader. And I asked him how he came up with their freemium pricing model. A data science team? A/B Testing? "No....
7+ Tips On How To Build Your First Sales Team
Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep...
Why SMB Reps Struggle in the Enterprise. And Vice-Versa.
Q: How is low/mid-ticket sales different from enterprise sales? They are very, very different. If I had to boil down how to filter potential sales professionals based on just 1 controlling criterion, it would be deal size. Enterprise sales: Reps often hunt many of...
The Top 50 SaaStr Answers on Quora in 2020
It's been a fun experience being on Quora for ... a decade 🙂 We've crossed 60,000,000 views of our answers there, so let's take a look at the Top 50 most viewed SaaStr Answers on Quora in 2020: Why do many startup owners sell...
7+ Tips On How To Build Your First Sales Team
Q: How do you structure a sales team when you’ve got zero experience doing sales? Well, first go get some experience with sales. 🙂 At least, close the first 10 customers yourself. If you don’t, you’ll never have any idea how to do it. And the odds your first rep...
Can an Entrepreneur Back Out of a Signed Term Sheet Without Damaging Their Reputation?
Can an entrepreneur back out of a signed term sheet without damaging his/her reputation? I’m going to say Yes, probably. There is a lot of drama around broken term sheets. Mostly around VCs backing out, not founders. But here’s the thing — term sheet are term sheets....
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