My Top 10 Lessons in GTM at SaaS B2B Startups

I am working at my fourth startup. I have been in various roles including: 1. **Series A** Regional Sales Director (A to C) growing a territory from $1m to $10m in 2 years 2. **Series B** Head of N America Enterprise (B to C) from $1.5 to $4m in 1 year 3. **Seed** Head of WW Sales (Seed to C) $0-10m ARR, $500M exit in 3.5 years 4. **Seed** Head of WW Sales (Seed to A, on track for B early 2025) $100k to $2m ARR in 1.5 years Some of my lessons learned. 1. Managing up and collaborating well with peers is even more important than just leading direct reports well, of course that’s also vitally important. 2. Culture is a bigger differentiator than product features, you need those too but great companies win bigger than just great products. 3. Most of the answers are available in the market if you listen before or after talking- it’s not enough to focus on the 10% of customers that buy, make sure to track why the 90% aren’t buying to get to product market fit. 4. Good branding isn’t necessary unless you want to be great- does brand kill a deal? Yes, all the ones you’re not in because you are looking at the wrong data. 5. Create a safe place for everyone and anyone to give feedback and make suggestions, the founders might be the smartest and most driven but hiring great people and telling them what to do all the time is a waste of intellectual capital. 6. Make pricing wildly easy for customers to understand and justify. Don’t get over confident in value early on before you have momentum, you can get greedy and lose to better known competitors or just other startups that make pricing easy- win on value but get the logo. It’s too hard to find business early on, don’t a customer that could do a case study and give you referrals slip away due to a spreadsheet about COGS. 7. The little things matter. Creating company values, for example, can seem like a waste of time when you’re burning it on both ends. Having a North Star to point to when making hard decisions on people, product, and priorities is crucial. 8. Move fast and break things. Pretty sure I stole this from Facebook or something. Processes are important but so is agility, be flexible, try things, pivot and improve. I’ve lost deals at early startups I could never have imagined losing at bigger more reputable companies, but we only made those mistakes once and they led to many more wins. 9. Intellectual honesty is crucial, while we need our founders to be unwavering and determined, we have to tell the king when he has no clothes. Just because a customer is talking to us doesn’t mean they’ll buy, and just because something worked with our current customers doesn’t mean we should stop improving. Do the hard things. 10. We are never as good as we think we are, we are never as bad as we think we are. Always learn and improve, regardless whether you win or lose a deal. Do lots of debriefs after customer meetings. P.S. Have fun. It’s stressful but life is short. It’s easy to get emotional, let things take a toll on you and your family. But make sure the size of the reaction is in line with the size of the problem. Don’t let competitiveness, or comparing yourself to peer successes, get in the way of appreciation for our opportunity. We are privileged to have an interesting challenge and a potential for great financial upside if we succeed. Don’t let a tough situation get in the way of seeing the daily and weekly successes at work and at home. Best of luck out there 🫡