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SaaStr Q&A
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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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Blog Posts, Early, Q&A
8 Signs of a Failing Sales Rep
Q: Dear SaaStr: What screams “I’m a terrible salesperson”? A few telltale signs: Immediate, massive discounting. Because they have no other idea how to close a deal or create urgency….
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Blog Posts, Q&A
Dear SaaStr: Can A Great Sales Rep Sell Any SaaS Product?
Not really in SaaS. At least not well. The classic “Sell Me This Pen” test is still a good one, even in SaaS. There is no perfect answer, but it…
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Early, Leadership, Other, Q&A
Quality of Life: What Does It Mean For A Start-Up?
Recently, I spent several hours with a new but great friend who has been on a vaguely similar journey to me. This friend is one of the hardest working people…
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Blog Posts, Marketing, Marketing, Q&A
Dear SaaStr: How Can I Get Sales and Marketing to Work Better Together?
How can Sales and Marketing work together? The simplest way is to get sales and marketing to work together is to (x) align marketing’s #1 goal to a revenue-related “commit”…
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Blog Posts, Customer Success, Early, Hiring, Q&A
Dear SaaStr: Who Should Our First Head of Customer Success Report To?
Q: Who Should Our First Head of Customer Success Report To? Ah, who should Customer Success report to. It’s not super simple. There are generally 3 options in the early…
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Blog Posts, Early, Fundraising, Q&A
What VCs are Really Looking For: Signs
Q: How do VCs pick which seed investments to make? There is one common factor, that founders know, but often lose track of in their pitch: every VC, at any…
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Blog Posts, Q&A, Sales
5+ Ways to Better Motivate Your Salesteam
Q: How can I better motivate my sales team? A few thoughts: First, make sure at least 1 or 2 of your first 5-6 reps are making a lot of…
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Fundraising, Leadership, Q&A
Dear SaaStr: How Do VCs Mitigate Investment Risks?
Q: How Do VCs Mitigate Investment Risks? There are a number of slightly subtle things the best VCs do, and the rest really don’t: Getting other investors to carry their…
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Blog Posts, Exit Strategy, Q&A
Dear SaaStr: When Should a CEO Walk Away From an Acquisition Offer?
Q: When should a CEO walk away from an acquisition? I’ve thought about this a lot. I’ve walked from acquisitions where I, to be honest, did want the money but…
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Blog Posts, Fundraising, Leadership, Q&A
Dear SaaStr: How Common Is It For Founders To Get Some Liquidity in A Venture Round?
Q: How Common Is It For Founders To Get Some Liquidity in A Venture Round? These days, if you raise money at a >=$80m-100m valuation, and are oversubscribed, most bigger…
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Blog Posts, Customer Success, Q&A
A Top Customer Success Hack: Driving Up Activation Rates, ASAP
Q: What are the most effective ways of increasing SaaS activation rates? In the early and middle days in customer success, we tend to talk about several core goals and…
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Blog Posts, Early, Q&A
Dear SaaStr: If So Many Startups Fail, Why Does Everyone Want to Do Them?
Q: If 90% of start-ups fail, then why does everyone want to make a start-up instead of a simple business? Folks want to start startups because they have a chance…
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Blog Posts, Early, Marketing, Marketing, Q&A, Sales
Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers?
Q: Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers? Overcharge if the customer is big, i.e., >$50k-$100k a year or so in ACV. Undercharge if the customer is…
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Blog Posts, Exit, Q&A
Dear SaaStr: How Much Do Founder-CEOs Own at Time of Exit?
It can vary a lot, of course. If you never raise venture capital, the founder-CEO might own 50%, or even 100% in some cases. The founders of $10B+ Mailchimp still…
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Blog Posts, Early, Q&A
Dear SaaStr: How Do Startups with 3 Founders Structure Their Board of Directors?
Q: How do startups with 3 founders often structure the Board of Directors to prepare for a Series A financing? Most traditional VCs will prefer 2 “Common” seats after the…
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Blog Posts, Customer Success, Marketing, Marketing, Q&A
Dear SaaStr: My Customer Missed the Deadline for AutoRenewal. How Do I Handle This Situation?
Q: Dear SaaStr: My Customer Missed the Deadline for AutoRenewal. How Do I Handle This Situation? Let it go and Move On. At a practical level, it is incredibly difficult…
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Blog Posts, Early, Q&A
Dear SaaStr: I’m Bootstrapped. How Can I Afford to Hire Any VPs?
Q: 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 skills…
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Blog Posts, Product, Q&A
Dear SaaStr: Have All the Good SaaS Ideas Been Built?
Dear SaaStr: Have All the Good SaaS Ideas Been Built? Sort of, but it’s OK. Why? What software can do in each category keeps evolving, and keeps getting more sophisticated,…
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Blog Posts, Career Growth & Advice, Growth, Hiring, Product, Q&A
Dear SaaStr: How Long Should a CEO Continue Being the Head of Product?
Q: Dear SaaStr: How Long Should a CEO Continue Being the Head of Product? Roughly, for me, for as long as it’s about a 10-hour a week job. Or often,…
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Blog Posts, Q&A, SaaS Product Pricing, Sales
A Few Thoughts on Renegotiating Old, Way-Too-Good Customer Contracts
Q: How do you re-negotiate an unlimited seat site license SaaS agreement as VP of Sales? Or even just a “bad” contract you gave to a very early customer that…
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Blog Posts, Leadership, Q&A
Dear SaaStr: What Are the Qualities of a Good Co-Founder?
Q: What are the qualities of a good co-founder? Life hack: partner with someone better than you that still finds you charming. Jokes aside, starting something is hard, the only…
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Blog Posts, Early, Q&A
8 Things That Kill Early Stage SaaS Companies. And 3 That Don’t.
Q: What is your opinion on the factors causing SaaS businesses to fail? My top list of what causes SaaS startups to fail: Not committing to 24 months to get…
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Blog Posts, Q&A, Sales
Dear SaaStr: What Would Be a Fair OTE for a VP Sales With a $1M quota?
Q: Dear SaaStr: What Would Be a Fair OTE for a VP Sales With a $1M quota? $0 or {null} Let me step back. I don’t think it makes any…
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Popular Q&A
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....
The Playbook to Scaling Your Team in Hypergrowth with Flexport CRO Ben Braverman (Video + Transcript)
Ben Braverman explains how Flexport entered a competitive market with a unique model and continues to grow. Hiring senior leaders can set companies up to fail and see how sticking with a current, successful model can be the key to hypergrowth. Rely on your success,...
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