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Blog Posts, Q&A
Dear SaaStr: What are Some Early Signs a New VP isn’t Going to Be a Fit?
Q: Dear SaaStr: What are Some Early Signs a New VP isn’t Going to Be a Fit? The top one for me is when they don’t embrace the goals given…
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Blog Posts, Early, Q&A
Dear SaaStr: Do Salary Increases Help With Retention?
Dear SaaStr: Do Salary Increases Help With Retention? I’ll defer to those with more data than me, but here’s what I’ve learned across 3 startups of my own, and investing…
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Blog Posts, Early, Q&A, Sales
The 9 Qualities of a Great Sales Rep
Q: What qualities do great salespeople have? A few: They really listen. Mediocre sales reps just start diving into their script, and try not to deviate from it. Great salespeople…
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Blog Posts, Company Culture, Early, Leadership, Q&A
Dear SaaStr: How Do You Know When it’s Time to Leave Your Current Company and Move On?
Q: How do you know when it’s time to leave your current company and move on? Let me add just one specific criterion / thought: -> Move on when people…
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Blog Posts, Early, Q&A, Sales, Sales
Dear SaaStr: What Are 5 Simple Tips to Quickly Improve Sales Performance?
Q: What are the best 5 points to improve poor sales performance? Here are my 5 simplest ideas to quickly improve sales performance. They don’t solve bigger problems, but they…
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Blog Posts, Hiring, Q&A
Dear SaaStr: When Does Hiring ex-CEOs Work Out?
Q: An entrepreneur created a start up and after struggling for 3 years had to close it and to look for a job. Would you see his adventure as advantage…
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Blog Posts, Fundraising, Q&A
Why It Matters Who Your “Lead” Investor Is
Q: What does a lead investor do? A lead investor: Is expected to lead any bridge round. This is super important. If the company does OK but Not Great, the…
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Blog Posts, Early, Q&A
Yes, It Can Take More Than a Year to Close a Critical Customer
Q: Did it ever take you a year to close a sale? Absolutely. It took me about 18 months to close Google, for example: Need identification and discussions with project…
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Blog Posts, Customer Success, Customer Success, Growth, Q&A
Just Seeing High App Usage Isn’t Enough. They May Still Be Preparing to Leave.
What were the signs you missed before you lost a major customer? I remember the first time I lost a six-figure customer. It was a surprise: They used the product…
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Blog Posts, Q&A
How Do VC Firms Pick Which Struggling Portfolio Companies to Support?
Q: How do venture capital firms determine when and how to help stalled or stuck portfolio companies? It is a super interesting topic more should be written about. You only…
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Blog Posts, Featured Posts, Growth, Q&A
9 Thoughts on What Makes For a Good Pricing Page
The more established your brand, the more complex your pricing page can be Because then, it becomes about what to buy — not from whom pic.twitter.com/1ag8jyPkmH — Jason ✨BeKind✨ Lemkin…
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Blog Posts, Q&A
Dear SaaStr: What Are The Best and Worst Parts of a Startup?
Q: Dear SaaStr: What Are The Best and Worst Parts of a Startup? The best parts: Having a great team. Once you really have a great team, not just some great…
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Blog Posts, Q&A
Dear SaaStr: What is the Typical Enterprise SaaS Cancellation Policy for $100k ACV/bigger Deals?
Generally, track to the cash: If a customer has signed a pre-paid annual or multi-year contract in exchange for a discount or other terms, then there’s generally no reason to…
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Blog Posts, Q&A
Should You Have Pricing Tiers? Yes. Almost Always.
Dear SaaStr: Why are pricing tiers so effective? I’m no pricing psychologist, but a few thoughts: Buyers like a >few< choices. Not too many, but 2 or 3. It empowers…
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Blog Posts, Growth, Q&A, Sales, Sales
Dear SaaStr: How Do I Set the Revenue Goals for Next Year?
Q: Dear SaaStr: How Do I Set the Revenue Goals for Next Year? I try to model 3 overall plans for the year: C-90, C-60, and C-10, not just for…
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Blog Posts, Q&A
Dear SaaStr: What is The Typical Conversion from Paid Pilot to Annual Contract in SaaS?
Dear SaaStr: What is The Typical Conversion from Paid Pilot to Annual Contract in SaaS? 70%+ once you are doing it right. Having said that, I’m not sure there is…
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Blog Posts, Career Growth & Advice, Early, Leadership, Other, Q&A
The Things You Have to Get Right When You Start a Start-Up
Everyone today wants to start a SaaS startup. They have an idea they are passionate about. They’ve worked under a great CEO and they’re ready — they think — to…
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Blog Posts, Growth, Q&A
Dear SaaStr: What Do The Top 1% of Sales Reps Do … That The Other 99% Don’t?
Q: Dear SaaStr: What Do The Top 1% of Sales Reps Do … That The Other 99% Don’t? I have a pretty good sense what the Top 10% do, though…
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Blog Posts, Customer Success, Q&A, Sales
5 Tips To Minimize “Churn and Burn” Behavior in Your Sales Team
As you scale your sales team, unless you are very careful whom you hire and how you train them, incentives being what they are in variable compensation, some negative behavior…
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Blog Posts, Customer Success, Growth, Q&A
9 Questions To Ask Candidates for Your First Head of Customer Success
The good news today, is there are tons of customer success veterans out there. So you can find folks to join you. Even just a few years ago, there weren’t enough folks…
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Blog Posts, Early, Q&A, Sales
Dear SaaStr: How Long Should You Give a New Sales Rep?
The tough truth is from 0.5–1.5 sales cycles. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty similar in SaaS at…
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Blog Posts, Early, Hiring, Q&A, Sales
Dear SaaStr: When Should You Make Your First Sales Op Hire?
In the “old” days, there was a rough rule that as soon as you are bringing on more than 1–2 reps a quarter, you needed to hire a director of…
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Blog Posts, Early, Q&A
Dear SaaStr: Is It a Good Idea to Start a Company with a Good Friend?
Q: Is it okay to start a business with your best friend? What is the talk we should have before the formation to ensure transparency and make sure our bond…
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Career Growth & Advice, Growth, Hiring, Leadership, Q&A
10 Tips to Avoid Burnout as a Founder
Q: As an entrepreneur, what are some tips and strategies to avoid burning out? It’s a huge risk. A lot of “pretty successful” startups all sell at about the same…
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Blog Posts, Early, Q&A, Sales, Sales
Dear SaaStr: As a CEO New to Sales, How Can I Get Better at Closing Deals?
Dear SaaStr: How Can I Get Better at Closing Deals? If it’s very early, hire 1 or ideally 2 sales reps who you’d personally buy from. You’ll all learn from…
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Popular Q&A
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...
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. But this was quite some time ago. And I asked him how he came up with their freemium pricing model. A...
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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