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Customer Success, Marketing, Q&A
The Two Things to Do. When You Don’t Know What to Do.
There may come a time, or two, in your company when you just don’t know what to do. When: You aren’t growing fast enough. and/or The competition seems to be…
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Blog Posts, Q&A, Sales
Why Enterprise Deployments Take So Long
Q: How long does it take to implement Salesforce for a mid-size company? Probably 6–12 months. Let me book-end it: When I was a VP at a Fortune 500 tech…
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Blog Posts, Compensation, Early, Leadership, Q&A
How Does a CEO/Founder Pick Their Own Salary?
Q: How does a CEO/founder/owner pick their salary? I’ll share my stories. In my first start-up, we raised $9m in our seed round — a large first round, but the…
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Blog Posts, Q&A
5 Key Startup Lessons We Learned From Covid
Q: What are the top startup lessons we learned during Covid? A few lessons that maybe weren’t new, but that we relearned in 2020-2021: Things always bounce back. It’s just…
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Blog Posts, Q&A
The 7 Simple Reasons So Many Companies Are Leaving the SF Bay Area
Q: Why are so many companies leaving Silicon Valley? It’s a combination of factors: We’ve all learned to work as distributed teams now. All of us. And what we’re learning…
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Exit Strategy, Q&A
Layoffs Are Less Common Today After Acquisitions. But Here’s When They Happen.
Q: After an acquisition, how long before severance packages are offered due to layoffs/downsizing? Layoffs and downsizing are less common in most tech acquisitions today. Why? Generally, most acquirers have decided its…
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Blog Posts, Career Growth & Advice, Early, Leadership, Marketing, Q&A
Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t?
Q: Dear SaaStr: How Do I Compete with a Company that has Unlimited Capital — and I Don’t? Do they have a strong brand? If not, it may not matter….
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Blog Posts, Q&A
5 Pros, and 5 Cons, to Taking a VC Round at a Very High Valuation
Why is it dangerous to accept too high of a valuation from an investor for a startup company? A lot of VC advice is a bit self-serving. There are risks…
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Blog Posts, Q&A
Dear SaaStr: What are Some Strategies to Get a Higher Price in an Acquisition?
What are strategies to justify a higher valuation for my company in an acquisition? The easiest “strategies” to get a higher price in an acquisition — which admittedly are very…
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Marketing, Marketing, Q&A
Dear SaaStr: If I Whitelabel My SaaS Product, Will it Hurt Me on Branding?
Q: If I White-label my SaaS, will it hurt me on branding my own company? Just do it. If it’s easy to do. Lots of folks agonize over white-labelling. The…
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Blog Posts, Q&A
VCs That Say “No” Now Really Might Say “Yes” Later. Here’s Why.
Q: What three things would take a VC from ‘maybe’ to ‘yes’? A true maybe — nothing. As the other answers have noted. A typical VC meets 100-300 start-ups a…
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Blog Posts, Fundraising, Q&A
Dear SaaStr: What is The Best Way to Prove You Can Be a Great VC?
Q: What is the best way to prove you can be a great venture capitalist? My learnings here are that it’s hard b/c every proxy has its issues. Basically, you…
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Blog Posts, Customer Success, Growth, Marketing, Q&A
Dear SaaStr: How Do I Convince My Customers with Monthly plans to Upgrade to Annual Plans?
Q: Dear SaaStr: How Do I Convince My Customers with Monthly plans to Upgrade to Annual Plans? My advice: Don’t. It’s too many calories expended for not enough benefit. Let…
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Blog Posts, Q&A
Dear SaaStr: We Lost an Enormous RFP Because We are Too Small. Any Advice?
Q: We lost an enormous RFP because we are too small. Any advice? This is indeed a big bummer. But it truly does make you stronger — if you commit…
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Blog Posts, Early, Q&A
What Inspires Founders to Create Startups
Q: What inspires founders to do it? I think for most founders I know, the real reason they start a start-up is that it’s the most interesting and stimulating thing…
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Blog Posts, Q&A
Dear SaaStr: What Are the Main Benefits of Being a VC?
It’s not all daisies and unicorns. But there are some clear benefits: Up to a point, significant freedom with your schedule. Board meetings and internal meetings are scheduled for sure,…
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Early, Fundraising, Q&A
Dear SaaStr: I’ve Been Advised to Restructure My Cap Table. What Do I Do?
Q: I have been advised to restructure our cap table by a VC. How do I structure an attractive cap table for future VC investment? Usually “restructure your cap table”…
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Customer Success, Customer Success, Early, Hiring, Q&A
Dear SaaStr: Who Should I Hire First to Get Customer Success Going?
Q: Dear SaaStr: Who Should I Hire First to Get My Customer Success Function Going? It’s easy — these days. Just hire a veteran. I don’t mean a true VP…
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Blog Posts, Early, Fundraising, Leadership, Q&A
Dear SaaStr: Why Do Venture Capitalists take Board Seats?
Q: Dear SaaStr: Why Do Venture Capitalists take Board Seats? It took me a while to figure this out. When I started writing venture (vs. angel) checks, the last thing…
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Growth, Marketing, Marketing, Q&A
Dear SaaStr: How Much (what %) of Revenue (ARR) Comes From Renewals in a SaaS Company?
After the early days — most. That’s just math. Of course, it varies. But one thing that is almost always true, is you get more renewals, more upsells, and more…
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Blog Posts, Early, Q&A, Sales
12 of the Most Common Mistakes Scaling Your First Sales Team
Q: What are the most common mistakes founders make hiring their first real sales teams? A few key mistakes I see start-ups making > 50% of the time: Hiring Early…
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Blog Posts, Career Growth & Advice, Hiring, Q&A, Sales
Dear SaaStr: What’s the Path to Becoming a Great VP of Sales?
Q: Dear SaaStr: What is the path to become a great VP of Sales? Each story is different, but there is one clear penultimate step: recruiting and managing a small…
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Blog Posts, Fundraising, Q&A
Dear SaaStr: Is It Better to Talk to a Partner, a Vice President, or a Principal at a VC Fund?
Q: Who are the key personnel in the VC organization and how can they help in the company connect with funding? Anyone that’s an investing professional, one way or another,…
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Blog Posts, Featured Q&A, Q&A, Sales, Sales
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…
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Career Growth & Advice, Growth, Leadership, Q&A
The 7 Best Pieces of Career Advice I Was Given
I’m not sure I’m a great giver of golden advice, but here’s my list of the best golden advice I’ve been given: Manage People — In General, and Earlier. The…
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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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