Dear SaaStr: How do I Convince My CEO that Marketing is Important? A lot of CEOs these days do seem to be late to truly invest in SaaS marketing, and most especially, to hiring a true VP of Marketing. I’m just shocked how many CEOs hack it to $5m, $8m, $10m+ in ARR without a…
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Dear SaaStr: Can a CEO be Late To Almost Everything? As CEO, I was basically never late. This year, for the SaaStrAnnual.com, every year we have perhaps ~150 top CEOs speak. Some of the very best in SaaS. CEOs of Atlassian, Box, Slack, Blackline, Qualtrics, The Trade Desk, Coupa, Algolia, MongoDB, Monday, Trello, Guidewire, and…
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Dear SaaStr: If you have old founders who left the company and kept their shares, on what valuation you buy their shares? Generally speaking, there are two paradigms: Buy them out at Common Stock price (which is what they in fact own), based on the lastest option pricing / 409a valuation; or Buty them out…
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Dear SaaStr: Do Referral Programs Work for SaaS? Well, for sure. But … it almost always takes longer than you think than direct sales: Salesforce announced a little ways back that its partners were the #1 source of its new bookings. 40% of HubSpot’s and Shopify’s and Gorgias’ customers come from agencies and other partners…
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Dear SaaStr: Is it Wise for Someone at 40+ to Think of Quitting Their Job and Becoming an Entrepreneur? Age doesn’t matter — per se. You’re not “too old” to do a start-up until you think you are and feel you are. And in B2B SaaS, the domain expertise and experience that come with more…
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Dear SaaStr: Why Might the Founder of a Company Appoint Someone Else as CEO? Because you should always be asking yourself, if everyone in a senior role is the right person for the next stage. Including you. Most of your VPs won’t scale all the way from $1m to $100m in ARR. So you need…
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Dear SaaStr: Should I Stay Solo or Should I Settle for a Co-founder? I think this is one of the Top 5 most important questions in start-ups. Possibly, Top 1 in ultimate significance. The answer for most of us: (x) most of us benefit from an A+ co-founder but (y) do not settle. The #1…
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Dear SaaStr: Can I Position My Startup To Be Acquired By The Likes of Google, Salesforce, Adobe, etc.? No. But … Sort of. What I’ve learned being on both sides of acquisitions, and being a 2x acquired founder — is: There is a List. There’s an informal CEO list of “jewels” the CEO would like…
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Dear SaaStr: Would You Invest in a Start-Up With 6 Co-Founders? I’ve done it — once. At least with 5 true co-founders. And that startup did end up selling for over $1 Billion (!) — so it’s not a firm “No.” But it did have the exact issues you’d expect. The downside? The company was…
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Dear SaaStr: My Startup Was Acquired and The Energy is Gone. What Should I Do Next? My first suggestion is: Learn. My second suggestion is: If Not, Then At Least Be Cool. I know you probably sort of hate working in that BigCo corporate environment. I sort of hated it too. And I didn’t make it 3…
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Dear SaaStr: Does the reverse vesting procedure for founders raising a VC round usually have a new 1-year cliff? Generally no. “Reverse vesting” can sound like a draconian VC term, and it may almost be triggering the first time you hear it. But it’s actually both (1) very common when founders are fully vesting in…
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Dear SaaStr: Does a SaaS Startup CEO Need to Have Sales Skill? Yes, if you have customers that talk to humans. Possibly no, if you only have “users” and/or are a freemium + no-touch model. If you build Dropbox or Squarespace or even Shopify to some extent, maybe you don’t have to be great at…
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Dear SaaStr: Can a SaaS Company Get to 50% Profit Margins? It’s possible, though it does require a very efficient model. The biggest, most mature software leaders aren’t quite there — but they are close. Adobe is currently at 45% non-GAAP operating margins: Microsoft, also mature and at scale, is also at 45% operating margins:…
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Dear SaaStr: Who Drafts the Term Sheet, The Entrepreneurs or the VC? It depends who is selling and who is buying. In the old days, and still mostly commonly today, term sheets only came from VCs. Founders were almost always selling. Well, almost always. But even in the Old Days, the hottest of start-ups made…
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Ben Chestnut, Mailchimp’s Co-Founder, talks Everything that Breaks on the Way to $1B ARR and their $12B Acquisition with SaaStr Founder & CEO Jason Lemkin

Dear SaaStr: How Can a SaaS Business Reactivate Churned Customers? This may sound simple, but the #1 thing you can and should do is create a series of marketing campaigns targeted only to churned customers. You will get some back, especially if you have a High NPS in general and most of your customers like…
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Dear SaaStr: Is It Normal for a Startup to Not Disclose Burn Rate and Other Details to its Employees? It really varies, but in my ecosystem, I’ve seen more transparency over the years, which is good. Transparency builds trust: I’m 100.00% in favor of transparency in general. And specifically, I believe employees should generally know…
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Dear SaaStr: What should I know about getting acquired? My top 5 tips: #1. Listen more. Talk less (on the target side). It’s very difficult to invent an acquisition. It’s almost impossible to create one, though it happens sometimes. Listen and learn. Understand what everyone’s motivations are. Why your champion is doing the deal. People…
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Dear SaaStr: Do Shares Get “Forward Vested in an Acquisition? Stock vesting is accelerated very rarely in an acquistion. In 95%+ of cases, the acquirer wants folks to keep vesting just as before — or more so. Even where the option agreements or bylaws or other legal documents require it, acquirers often require those agreements…
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Dear SaaStr: What does a COO do in a tech startup/company? How would the team be structured? Can you give an example? COO is a bit of a made-up job. What I mean is, there is no organizational “need” for a COO per. You need a CEO. You need a VP of Sales, Product, Marketing,…
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Dear SaaStr: How Can I Reduce Our Churn Rate in SaaS? You’ll get a ton of advice, but two high-level efforts always work to ground your efforts here: Measure it, segment it — and make it a core goal to drive it down. I’ve yet to work with a SaaS company that made driving down…
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Dear SaaStr: How Do I Manage a Salesperson Who Does Not Follow Up on Sales Opportunities? The simple process you need to add is an “SLA”. You need to take away leads, and also opportunities, if they are not followed up with in a prompt fashion. This is fairly easy to implement in Salesforce (or…
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Dear SaaStr: Has Salesforce Overpaid for its Acquisitions, Including the $27.7 Billion Acquisition of Slack? Possibly, but it probably doesn’t matter all that much. Why? It needed them. It needed its top acquisitions to keep growing. They worked: Mulesoft, Tableau, Slack, ExactTarget, etc have all become core businesses that are necessary for Salesforce to grow….
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Dear SaaStr: Could you tell about the very first time you approached investors and how you proceeded in detail? The first time I approached investors it went well — until I blew it. I did start off with some privilege. While I hadn’t raise money before myself, my past bosses had. I asked them for…
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Dear SaaStr: Is It OK To Have a 5% Response Rate in My Personalized Cold Emails? Yes. 5% isn’t a huge response rate, all things being equal. You are sending a ton of emails and perhaps they aren’t personalized enough. Still — a 5% true connect rate — where they will take a call and do…
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