Outbound Always Works. If You Do It Right. And You Put In The Time.
"Crummy outbound may not work that well these days. But great outbound still works like magic." pic.twitter.com/DwjcgRLOVA — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) January 31, 2025 These days, it can really feel like the Old Bag of Sales...
Hiring Risks vs. Hiring Flags. Make Sure You Get it Right.
My biggest hiring mistake I've made past 5 years that I never made before: I hired folks who didn't really, really, really want the job So far, none have worked out — Jason ✨👾SaaStr 2025 is May 13-15✨ Lemkin (@jasonlk) April 16, 2025 During the...
Eventually … Almost Everyone Has a Sales Team
The lure of freemium (like The Force) is strong. No headaches. Customers try and buy all on their own. Like magic. The appeal of No Salespeople can be strong. And freemium is certainly back in the Age of AI. ChatGPT, Claude, Cursor, Canva and more have all...
Before You Start as a VP — Please, Please, Please. Do a 60-Day Plan. And Make Sure the CEO Agrees With It.
If you’re feeling relieved you finally got that great VP to join the company, read this from @jasonlk next. (And if you are that VP, definitely read it first.) https://t.co/cVodwksp3N — James Cham (@jamescham) July 23, 2022 I’ve now worked with or invested...
That Super-Successful VP of Sales. Great? Or Just Lucky?
I get sent this resume to review all the time. Director+ of Sales at Slack / Zoom / Mongo / Datadog / Qualtrics Your Brand Name SaaS Company. Took Hot Start-Up from $0 to $50m as VPS from Day 0. Was there “early” through IPO and did amazing things. That all sounds...
Dear SaaStr: How Does a First Time Founder Identify 10x Hires?
Dear SaaStr: How does a First Time Founder Identify 10x Hires? How do you hire a great CTO, a great VP of Product, a great VP of Sales … if you’ve never worked with one? It’s hard. If you haven't worked with one before, then, yes, 10x engineers...
Dear SaaStr: One of Our Most Respected Team Members Quit and Folks Are Leaving. What Do I Do?
Dear SaaStr: One of Our Most Respected Team Members Quit and Folks Are Leaving. What Do I Do? Promote someone great that everyone respects into a leadership role. Right now. This is really the only answer I’ve seen to this situation. We’ve all been in it at least to...
Dear SaaStr: What’s The Toughest Skill to Learn to Scale in B2B?
Dear SaaStr: What’s The Toughest Skill to Learn to Scale in B2B? You need to learn to become a parallel recruiter. To constantly, painfully, boring-ly be recruiting the next level of management and managers — all the time. Doing 30+ interviews a month — minimum....
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers?
Dear SaaStr: Should SaaS Startups Really Have CROs or COOs? Is That Too Many Management Layers? A few years ago, I would have said No. There’s no way a SaaS startup needs a “CRO” or “COO” or other C-level Officers Without a Clear, Single Functional Area to Own Until...
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...
Dear SaaStr: What Are The Top 3 Criteria for Hiring Your First Head of Sales?
We’ve talked a lot on SaaStr about hiring that first VP of Sales. But what if you can’t find the right person, and you’ve spent months looking? What risks should you take when you’ve realized Ms or Mr Perfect just isn’t going to happen...
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: How Long Should a CEO Continue Being the Head of Product?
Dear SaaStr: How Long Should a CEO Continue Being the Head of Product? Roughly — only for as long as it’s about a 10-hour a week job. Or often, maybe only up to $3m-$5m in ARR or so. These days, especially, I see way too many SaaS companies at $8m-$10m ARR or beyond...
Founder SaaStr
Related Posts
Industry News
- Klarna seeks growth beyond buy now, pay later as its stock goes public
- CoreWeave CEO says AI demand is 'overwhelming'
- Most of Elon Musk’s fortune now comes from his private companies
- Adobe’s Generative AI Credit Rules Explained for Lightroom and Photoshop
- Oracle’s not-so-secret weapon that’s helped it quickly take on the cloud giants
- Alibaba leads US$60 million investment in AI video generation start-up AIsphere
- Via eyes acquisitions after completing $493M NYSE IPO at $3.65B valuation | CTech
- Elon Musk's xAI Reportedly Lays Off 500 Workers From Data Annotation Team As Startup Pivots To Specialist AI Tutors For Grok Expansion
- Micro1, a competitor to Scale AI, raises funds at $500M valuation
- Klarna gives employees a rare chance to cash out their shares during the IPO window