Dear SaaStr: Who Should Our First Head of Customer Success Report To?
Dear SaaStr: Who Should Our First Head of Customer Success Report To? Ah, who should Customer Success report to. It’s not super simple. And it’s changed a lot the last 18-24 months in SaaS and Cloud. There are generally 3 options in the early and middle days:...
Dear SaaStr: What is The Biggest Difference Between Running a 10 Person Startup and a 100 Person Startup?
The biggest structural difference is you have to hire all the VPs by employee 50–100. You won’t be able to scale this far without a full management team — VPs of Sales, Marketing, Product, Engineering, Customer Success at least. But the toughest personal challenge for...
Your (Belated) SaaS New Year’s Resolution: Add a Layer
I know you don't do OutboundEventsWebinarsTravel to customers Have a BD teamOffer enterprise edition And you are doing great But what if you did? — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) January 13, 2025 I agree with most Start-Up Truisms. One...
Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder?
Dear SaaStr: What Are The Biggest Problems You Face as a Startup Founder? The list of problems is endless (this is one of the hardest parts of the job), but let me try to order a few of the biggest challenges roughly based on stage: Top issues you face as a startup,...
The #1 Worst Hire of All When You Are Just Starting To Scale: The Mediocre VP of Engineering
Every time I see a CRO that doesn't sell themselves, they fail. Every time I see a CTO that doesn't code themselves, they fail. Every time I see a CMO that doesn't market themselves, they fail. — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) November 28, 2024...
Dear SaaStr: What Are Some Successful SaaS Leaders Without Sales Teams?
Dear SaaStr: What Are Some Successful SaaS Leaders Without Sales Teams? Many that are self-serve and SMB-focused can start off without a sales team … for a while. But almost none stay without a sales team … forever. Yes, Atlassian since well past its IPO...
What Really Works When Hiring VPs, and How M&A Really Works, with HubSpot Co-Founder and Chair Brian Halligan + Jason Lemkin
HubSpot Chair and co-founder Brian Halligan and SaaStr CEO Jason Lemkin share their advice on what actually works when hiring your SaaS executive team.
Dear SaaStr: How Far in SaaS Can a 10 or 20 Person Team Go?
Dear SaaStr: How far in the SaaS can a 10 or 20 person team go? I know many are talking about AI fueling 1 person, $1B start-ups. I hope that happens. But maybe … not so much in SaaS. Today, the most efficient public SaaS company is probably Doximity, at about...
Dear SaaStr: What Was Your First Step When You Decided to Do a Startup?
Dear SaaStr: What Was Your First Step When You Decided to Do a Startup? For me, both times, it was to find my co-founder. In my first start-up, arguably I invented the idea of the company, but my co-founder invented the technology. It was really all her. Step 1 was...
Round Trip Employees: When It Works & When Maybe It Doesn’t
My second boss came from a very big, very old tech company. He inherited one of their firm rules: “When you leave, if you leave … you can’t ever come back!” I didn’t get that rule. If someone great left, wouldn’t you want them...
Before You Start as a VP — Do a Real 60-Day Plan. And Make 100% Sure the CEO Agrees With It.
I’ve now worked with or invested in ~35 successful start-ups beyond my own companies and I’ve watched a lot of VP hire train wrecks. Probably the most common is “the wrong VP of Sales”. We’ve talked about that for 6+ years on SaaStr, and...
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO?
Dear SaaStr: What Role Do Founders Play Once They Hire an Outside CEO? Let me take a slightly different take on the question. Maybe you are really asking – “Am I still on the hook if we hire a ‘real’ CEO to run the company? ‘Cause...
Dear SaaStr: Why did Jason M. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups?
Dear SaaStr: Why did Jason M. Lemkin Change his Point of View on The Value of a COO for Earlier Stage Startups? I try to work with (and invest in) CEOs that are better than me. I found, when I was a SaaS CEO, that the CEOs that complained about needing a COO early,...
Dear SaaStr: If a Startup at $1.5M ARR is Hiring a COO, How Much Equity Should They Get?
Dear SaaStr: If a startup is at $1.5M ARR and is looking to hire an experienced COO how much equity should they give him/her? 0%. I think $1.5m ARR is too early for an experienced COO in 95 cases out of 100 — unless it’s a total rocketship and you plan to...
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