Dear SaaStr: What’s The Best Way to Set Targets for the Sales Team?
Dear SaaStr: What’s The Best Way to Set Targets for the Sales Team? First, I try to model 3 overall plans for the year: C-90, C-60, and C-10, not just for the sales team, but the whole company. The C is for “Confidence”. The odds you think you...
Dear SaaStr: What’s The One Trait You Look for When Assessing an Inside Sales Candidate?
Dear SaaStr: What’s The One Trait You Look for When Assessing an Inside Sales Candidate? I break it into two stages: In the early days, when you as founder/CEO are recruiting and managing the salesperson yourself, then the #1 most important criterion is that you would...
Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales?
Dear SaaStr: Does It Make Sense to Have Post-Sales Functions Report into Sales? In many ways, this is the question of the day. So many SaaS companies, faced with slower growth, are moving CS in particular in to the sales department, trying to get more growth from the...
Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup?
Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup? Yes. Most of us will feel like a pest when we start doing outbound. So … get better at it, get over it, and hire folks who know how to do it. Sales is hard. It’s being told No...
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make?
Dear SaaStr: What’s the #1 Mistake New Sales Leaders Make? Let me just summarize my #1 observation here: the top mistake first-time sales managers make is recruiting. In that — they can’t do it. They can’t recruit great reps. They can recruit some mediocre...
Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition?
Dear SaaStr: As a Startup, What Are Some Effective Ways For an Underdog to Take Down Their Competition? It depends on the gap. In B2B historically, I’d argue if your competitor is larger than you, at $8M-$10M+ in ARR and growing quickly, with even reasonably...
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It?
Dear SaaStr: A Big Tech Co Launched a Competitive Product. How Can I Tell How Serious They Are About It? In B2B at least, I’ll give you a few metrics that are fairly reliable. The classic one still works, but in 2026 you need to layer in some new signals too....
Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At?
Dear SaaStr: Should Your Ask a Prospect What Competitors They Are Looking At? Yes. And in 2026, more than ever. You’ll find 90% of the time you’ll want to not just tell a prospect who you are competing with, but do so aggressively. And box the competition...
Dear SaaStr: How Do I Convince My CEO that Marketing is Important?
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 B2B marketing, and most especially, to hiring a true VP of Marketing. In the Age of AI, so many CEOs hack it to $5m, $8m, $20m+ in ARR...
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started?
Dear SaaStr: Should a Startup Founder Handle Sales Themself When First Getting Started? The answer is yes – 95% of the time. The “best” sequence for building a repeatable sales engine is roughly: The CEO/founder should close at least the first 10 (or 20 or...
Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS?
Dear SaaStr: How Big Should The Addressable Market Be to Go into Vertical SaaS? To win in Vertical SaaS: – Can you charge at least $10k a year?– Can you add enough value to hit 110%+ NRR?– Can you get to 60% market share? If so, in many markets,...
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep?
Dear SaaStr: What Sales Comp Plan Should I Use For Our Very First Sales Rep? At the end of the day you have to solve for two things: A plan that gives the reps a living, fair wage; and A plan that you know and feel is accretive to the company. Sales reps have to be...
Dear SaaStr: What Was Your Very First Sales Story? How Did It Go?
Dear SaaStr: What Was Your Very First Sales Story? How Did It Go? My very first sales deal was for $6,000,000. In my first start-up, I was mostly hunting whales — seven-figure and eight-figure deals. I had no experience doing any of this. For our First Big Customer,...
Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers?
Dear SaaStr: Should We Over-Charge or Under-Charge our First Customers? My general rules: Overcharge if the customer is big, i.e., >$50k-$100k a year o nor so in ACV. Undercharge if the customer is smaller by revenue. There’s a method to the seeming madness...
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