Dear SaaStr: I’m Joining a B2B Startup at $3m ARR as VP of Sales. What Should I Do First?
Dear SaaStr: I’m Joining a B2B Startup at $3m ARR as VP of Sales. What Should I Do First? Stepping into the VP Sales role at a company with $3M ARR is a pivotal moment. At this stage, the company has likely found some product-market fit, but scaling efficiently...
Dear SaaStr: What Sales Techniques Helped You Consistently Succeed While Others Failed?
Dear SaaStr: What sales techniques helped you consistently succeed while others failed? A few that basically always work in sales … but that so many don’t do actually do: Being a product expert. 95% of the sales execs I talk to in software don’t know the product much...
Dear SaaStr: How Many Investor Updates and Meetings Do I Owe My Investors?
Dear SaaStr: I am a startup founder that writes extensive monthly report to investors. We are also doing weekly meetings, are they asking for too much of my time? Yes, that’s too much. Some rough rules: For every 1% of a company an investor owns, they get one...
Dear SaaStr: What’s a Big Check for a VC Investor?
Dear SaaStr: What’s considered a large amount of money for an investor? The answer isn’t obvious from the outside. And it’s something founders should know. Is $1m a lot? $100k? $20m? It really varies by VC and by fund. A rough answer is...
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: How Long Should You Give a New Sales Rep?
Dear SaaStr: How Long Should You Give a New Sales Rep? The tough truth is from 0.5–1.5 sales cycles. And yes this is true even in tougher times. Probably even more so in tougher times. Sales is tough. It’s a lot of Nos to get to a Yes. And while sales is pretty...
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: How Do I Know If My New VP of Marketing Is Working Out?
Dear SaaStr: How Do I Know If My New VP of Marketing Is Working Out? It’s tough. Way too many senior marketers today just want to be strategists. Or just manage a few agencies and work on brand. That’s not what you need. You’ll know if your VP of...
Dear SaaStr: Should I Remove Monthly Subscriptions to Drive Down Churn?
Dear SaaStr: Should I Remove Monthly Subscriptions to Drive Down Churn? Generally — no. Annual plans only mask churn. They don’t eliminate it. And at least for SMBs and prosumer customers, not having a monthly edition can add significant friction to...
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...
Dear SaaStr: What’s It Like to Have Your Company Acquired by One of the Tech Giants?
Dear SaaStr: What’s It Like to Have Your Company Acquired by One of the Tech Giants? It’s a lot of change. The pressure is mostly or at least partially off. Unless there is a huge earn-out or retention payment tied to performance, the pressure is off. Not all of...
10+ Simple Tips To Help Any Account Executive Close More
Dear SaaStr: How can I boost my sales if I am in B2B sales? My top tips for AEs: Grab your CEO and bring her into bigger deals. Ask your CEO to join you on a few sales calls a month. Deals will close at a higher rate if the CEO joins. Customers love to talk to...
In SaaS, The CEO Never Gets to Step Away From Sales
The biggest mistake you can make as a founder when you hire your first VP of Sales is stepping out of sales I see this again, and again It only works with the very best VPs of Sales Every other first VP of Sales needs you doing at least half of what you were doing...
Dear SaaStr: What are Some Early Signs a New VP isn’t Going to Be a Fit?
The top one for me is when they don’t embrace the goals given to them. Sometimes it’s subtle, sometimes it’s aggressive and overt. What I see this again and again: A VP of Sales that just sort of ignores the plan for the next quarter or two. A CMO that focuses on the...
Founder SaaStr
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