The Advice That Stings is The Advice You Want to Hear
The advice that stings is the advice you need to hear. Many folks are saying everyone from our kids to our SVPs and CEOs can’t take criticism anymore. It does seem to be more true, in my experience. VCs are reluctant to be critical of founders, even as they run out of...
Dear SaaStr: How Do Investors Feel About “Acquihires”?
Dear SaaStr: How Do Investors Feel About “Acquihires”? Back when I started investing, in 2013, VCs worked on getting acquihires for their struggling startups. A lot of energy was put in to find a “soft landing” for struggling investments...
5 Interesting Learnings from Blackline at $600,000,000 in ARR
One of the most powerful things in SaaS is having a visionary founder-CEO. Nothing against an outside CEO. Sometimes, the time comes to hand the baton to someone else. But, but — only a founder CEO can execute a vision over 20+ years. Only a founder CEO knows...
Mastering Partner Marketing: What NOT to Do and How to Excel with Drata CMO Sydney Sloan
Welcome to the latest installment of our “What’s New” series where SaaStr founder and CEO Jason Lemkin sits down with some of the top leaders and founders in SaaS and Cloud to discuss What’s New and what should be top of mind for fellow founders. In the new episode, Jason sits down with Drata CMO Sydney Sloan to talk about what’s new at Drata, the role of CMO at Drata vs. Salesloft, partner marketing, customer marketing, and more.
Yes, It Can Take More Than a Year to Close a Big Customer
Dear SaaStr: Did it ever take you a year to close a sale? Absolutely. This is pretty common in the enterprise. It took me about 18 months to close Google, for example. And that was just for the initial group of users: Need identification and discussions with...
When a Struggling Customer Churns, You Learn How Important You Are
So lately I’ve listened to a few calls from churned customers from portfolio companies. It’s been a while since I listened to or talked to struggling customers. On the one hand, arguably, their feedback is not fully representative of your customer base if you’re...
High-Velocity Techniques to Maximize Sales with Gusto’s CRO and Head of Go-to-Market
Tolithia (Gusto’s CRO and Head of Go-To-Market Ops, or GTM Ops) and Jamie (Gusto’s Principal, GTM Strategy & Operations) about their high-velocity techniques for maximizing sales. They first discuss their aim of helping other professionals grow their businesses, the importance of proper territory management, especially in high-velocity, high-scale operations, and the difficulties of geographic territories. Following that, they discuss dynamic territory management, the problems of static sales books, and how industry does not necessarily dictate business models. They also touch upon tools and strategies they implemented at Gusto, such as the Next Best Action tool and dynamic books, to decide which leads to work and how. At the end of the discussion, they answer several questions from the audience.
SaaStr on Lenny’s Podcast: How To Build a World-Class Sales Organization
Lenny Rachitsky’s substack on product has over 650,000 subscribers (!) and Lenny asked us to join his podcast to talk about building a sales team — from the perspective of a product-first founder or exec. It was a pretty strong conversation and we took a...
Tech and Startups Have Changed. Do Founders Still Come Last?
So the other day I did a 20VC with Harry Stebbings, and one of the topics that came up was the Hopin founder’s $100m+ secondary that the CEO took out of the company. While the company is still around, the Hopin product was subsequently sold for pennies on the...
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