Dear SaaStr: When and how should SaaS startups offer reduced pricing vs the competition? For most B2B apps, you want to at least start with “just right”, Goldilocks pricing: #1. Too high a price, and you start to add friction to the sales process. Deals take longer, leads shop other vendors, etc. That may be…
Continue Reading

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 and predictably is the next big…
Continue Reading

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 at all. A huge miss as half…
Continue Reading

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 meeting / Zoom a year until you…
Continue Reading

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 investing more than 1.5%-2% of an individual fund into one deal is a…
Continue Reading

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…
Continue Reading

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 similar in…
Continue Reading

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, we’d been negotiating a $6m/year contract for…
Continue Reading

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 Marketing is working out by looking…
Continue Reading

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 buying. That means less customers & less sales. I’s a double-edged sword. It simplifies…
Continue Reading

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 here. You’re learning very quickly here if you are enterprise or mass-market…
Continue Reading

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 it. But the insane founder-CEO pressure you…
Continue Reading

  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…
Continue Reading

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…
Continue Reading

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 types of…
Continue Reading

Dear SaaStr: I’ve Been Out of Sales For 6+ Years. Is It Too Late to Get Back In? I stayed at home as a parent and then played professional poker for several years. Ok here’s the thing: you have 2 flags already (and staying home for the kids isn’t one of them). Issue #1 isn’t…
Continue Reading

Dear SaaStr: What are some benefits you can add to get people to buy a product besides discounts and add-ons? You can help them actually deploy your app. To actually, truly get the value out of it. Not just buy it. Buying a product is just Step 1, at best. Mediocre sales reps focus way…
Continue Reading

Dear SaaStr: What’s the #1 Most Important Thing To Look For In Your First Sales Rep? The #1 most important criterion for your first 2 reps is: would you buy from her? For real? Would you truly, 100%, buy your own product from them? 98% of the reps you interview … will fail this test….
Continue Reading

Dear SaaStr: What’s Your #1 Opener in Sales? The best opener is sharing how a very similar company or a competitor uses your product — and the exact specific ROI that customer gets. Everyone wants to know the playbooks of similar companies and competitors. How often does your sales team actually do this? Put in…
Continue Reading

Dear SaaStr: When should I pay the commission for SaaS sales? All of our trial signups will get an automatic email from an account executive. How do we decide if the AE was responsible for the sale versus the sale just happened organically? Every company with a self-serve component and a sales-driven component frets a…
Continue Reading

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 ones, but that’s about it. It is incredibly hard to figure…
Continue Reading

Dear SaaStr: What Qualities Make a CEO The Best In Their Industry? I’ve invested in 5 start-ups that had a $1,000,000,000+ cash exit or IPO. The CEOs were all quite different. Some extroverted, some introverted. Some wicked smart, some merely very smart. Some direct, some warm and friendly. But what made them great: Ability to…
Continue Reading

I pitched 150+ entities over the years as both a start-up exec and a founder. And now I’ve been on the other side of far more than 150 meetings as part of SaaStr Fund. Nothing in fundraising really phased me as a founder — for the most part. Except one set of meetings. Raising money…
Continue Reading

Dear SaaStr: What Was The Best Advice You Ever Got From an Angel Investor The best advice I ever got from one of my angel investors: Stop feeling sorry for yourself. I went to meet with one of my angels and mentors when things were probably toughest at my last start-up. My co-founder had walked…
Continue Reading

Dear SaaStr: Did it Ever Take You a Year Or More to Close a Sale? Absolutely. It took us about 18 months to close Google, for example: Need identification and discussions with project manager over several months About 6 on-site meetings to review need identification and discussion with broader group RFP Prototype of workflow Ensure…
Continue Reading