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 Were The First Five Hires You Made After Product-Market Fit?
Dear SaaStr: What Were The First Five Hires You Made After Product-Market Fit? My first 5 hires at Adobe Sign / EchoSign, beyond the core founding+ team, once we had paying customers and first, if early, product-marketing fit: #1:Â Full-time sales rep at $8k-ish MRR....
Dear SaaStr: How You Deal With Long Sales Cycles, E.g. 7-8+ Months?
Dear SaaStr: How You Deal With Long Sales Cycles, E.g. 7-8+ Months? "What's the best way to shorten a long saled cycle from 6 months to 4-5 months? Hire a truly great CRO / VP Sales. They know how to do this. They know how to move deals faster. How to talk to...
Dear SaaStr: What’s #1 On The Path to Becoming a Great VP of Sales?
Dear SaaStr: What’s #1 on the path to becoming a great VP of Sales? Each story is different, but there is one clear penultimate step: recruiting and managing a small sales team yourself. From scratch. What 95 times out of 100 is a recipe for failure is jumping...
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity
Dear SaaStr: My Co-Founder is Threatening to Quit Unless I Give Him More Equity; what should I do? Generally, this is the last, best chance to fix things. Founder equity splits are a tough thing. What seems fair on Day 0 may seem less fair on Day 720. The one that...
Dear SaaStr: How Do We Close Bigger Deals?
Dear SaaStr: How Do We Close Bigger Deals? If you already have a few bigger deals under your belt, but most are smaller … a few higher-level suggestions: #1. Hire a Very Good CRO / VP of Sales that has sold at your “high end” price point. They will be much better at...
Dear SaaStr: When My Startup Raises $10m, Would It Be Appropriate to Take a $170k Salary (no co founders)?
Dear SaaStr: When My Startup Raises $10m, Would It Be Appropriate to Take a $170k Salary (no co founders)? Yes, not a problem. You should take a “market correct” salary as soon as it’s economically immaterial to the company. I don’t write $10m...
Dear SaaStr: Should I Publish My Pricing?
Dear SaaStr: Should I Publish My Pricing? If you aren’t sure — then yes. Transparent pricing has many advantages: It makes the sales process simpler. It allows prospects and leads to do more discovery work on their own. And it places your app in pricing context with...
Dear SaaStr: I’ve Hired 2 SDRs. Can I Hire an AE to Manage Them?
Dear SaaStr: After closing a few deals myself as a founder, I hired 2 SDRs and closed some more. Should I hire an AE to take over the SDRs and close or a VP of sales? Try to find a VP of Sales now, and try to hire an AE now. You probably will find the solid AE...
Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market
Dear SaaStr: How do VCs Really Feel About Founder Salaries? I Was Told That a General Rule of Thumb is 75% of Market The 75% Rule once you are VC Funded for more than a few million dollars is a good one. But if you raise less than that — 75% may well be too...
The CEO Never Gets to Step Away From Sales
"The #1 mistake founders make when they hire their first VP of Sales? Or even just their first sales rep? They step back from sales. No. You don't get that time back. It's just what you do in sales, changes." pic.twitter.com/wwUzRvrbt0 — Jason...
Dear SaaStr: What’s a Fair Amount of Founder Secondary in a Series B VC funding round?
Dear SaaStr: What is considered a fair or happy medium secondary amount for the founders to take off the table at a Series B VC funding round? Secondary sales done right truly align founders and the company and incent them to go long.  See Brian Halligan’s (co-founder...
Dear SaaStr: Should You Ask a Prospect What Competitors They Are Looking At?
Dear SaaStr: Should You 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: If I Whitelabel My B2B Product, Will it Hurt Me on Branding?
Dear SaaStr: If I White-label my B2B product, will it hurt me on branding my own company? Just do it. If it’s easy to do. Lots of folks agonize over white-labelling. The brand benefits will go to my partner, not me. I’ll be valued less. Etc. etc. But bear in mind a...
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