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Blog Posts, Career Growth & Advice, Early, Leadership, Q&A

Dear SaaStr: What Were the Biggest Mistakes You Made Getting Your Startups Going?

Dear SaaStr: What Were the Biggest Mistakes You Made Getting Your Startups Going? The biggest two mistakes I made, I made twice, maybe thrice. They were: One, starting with too incomplete a management team. In my first start-up, while the core 3 co-founders were great, we needed an operational COO to really get to market…
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Blog Posts, Early, Fundraising, Leadership, Q&A

Dear SaaStr: Should Founders Start Their Vesting at Date Of Incorporation So They Have Vesting Prior to Raising VC Capital?

Dear SaaStr: Should Founders Start Their Vesting at the point of incorporation so they have shares vested prior to signing a deal with investors? No. At least, don’t do too much of this. I got this backwards, as do most founders. We think “being vested” protects us from VCs. Yes, there can be some corner…
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Blog Posts, Customer Success, Early, Marketing, Q&A

Dear SaaStr: How Many Of Our Prospects and Customers Should I Meet Face-to-Face?

Dear SaaStr: Should an early- stage B2B startup meet every customer face-to-face to receive feedback? March 2020 changed everything in SaaS, albeit we’re still working through all the changes on many levels. And it’s now a long time ago. In many ways, it’s just a different world. We’ve gotten used to closing bigger and bigger…
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Early, Fundraising, Leadership, Q&A

Dear SaaStr: Why Do So Many Start-ups Concentrate on Getting Investors?

Dear SaaStr: Why Do So Many Start-ups Concentrate on Getting Investors? Many of them shouldn’t. Selling stock is dilutive, and carries economic, social and legal obligations. Investors will expect 3x-100x returns on the capital, depending on the stage. They’ll want board seats, and consultation, and will often push your company to expand and grow in…
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Blog Posts, Early, Q&A, SaaS Product Pricing, Sales, Sales

Dear SaaStr: What’s a Resonable Discount for an Annual Contract? How About a 3 Year Contract?

Dear SaaStr: What’s a Resonable Discount for an Annual Contract? How About a 3 Year Contract? First — you don’t want a true net discount at all. What I mean what you want is a pricing structure that anticipates discounts so the net effect is revenue positive. Later, when you implement a CPQ and other…
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Blog Posts, Exit, Exit Strategy, Leadership, Q&A

Dear SaaStr: What Should Founders Do To Get Noticed By An Established Company’s M&A Team?

Dear SaaStr: What Should Founders Do To Get Noticed By An Established Company’s M&A Team? Don’t bother too much with trying to get “corporate development” or the M&A team’s attention. That’s not their job. Probably the most important thing to understand is that in 95%+ of tech companies, the “M&A team” does not drive M&A….
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Blog Posts, Early, Fundraising, Q&A

The Many Types of Angel Investors

Dear SaaStr: Are there different types of angel investors that should be sold differently when trying to raise money to start a business? There are several key types. Let’s break them into several categories: Professional vs. non-professional. Professional angels generally have very specific criteria in terms of valuations, team make-up, check size, etc. You do…
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Blog Posts, Early, Fundraising, Leadership, Q&A

Dear SaaStr: How Can I Remove a Troublesome Investor from my Cap Table?

Assume you can’t kick out investors. And plan accordingly. There are some limited exceptions, especially if you do nonstandard types of convertible debt or only raise a very small amount of capital. But for the most part, you are stuck with your investors forever. In the U.S. and Delaware and California, and under standard VC…
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Blog Posts, Exit Strategy, Q&A

Why Founders Leave After Acquisitions

Why do founders leave after their companies are acquired? There are many nuanced answers, but in the short and medium term, it’s incentives. Acquirers use 3 incentives to get founders to stay: Sticks. If you leave, you lose X% of the consideration. Acquirers try to put 30%-40% of the founders’ consideration at risk, if they…
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