P.S.I. Selling

Want to master some of the best sales ideas out there and some of the business concepts that SaaS salespeople need to know? These digests will get you up to speed quickly. Where should you start? If you're a sales rep, check out SPIN Selling to learn how to do great discovery, The Challenger Sale to see how to deliver a great pitch, and Strategic Selling to see how to manage a complex deal. If you're a founder, check out Obviously Awesome to see how to position your produ

"The Innovator's Solution" by Clayton Christensen and Michael Raynor lays out a framework for understanding disruptive innovation. Disruptive innovation creates both tremendous opportunities and existential threats for companies, making it one of the critical concepts driving modern corporate strategy. Salespeople who understand disruptive innovation can position their product as a way to drive strategic success, enabling them to attract interest from senior decision makers

In SPIN Selling, Neil Rackham argues that sales success requires building the customer's perception of value through effective questioning early in the sales process. He disagrees with conventional wisdom that argues that selling is about handling objections and deploying closing techniques. Rackham recommends that reps ask several layers of questions about the customer's problems and get the customer to articulate the importance of solving those problems. This book is valua

In "Good Strategy/Bad Strategy," Richard Rumelt presents a clear framework for understanding effective business strategy. Good strategy is about identifying the one or two critical issues in a business situation and concentrating effort on these pivot points. Effective strategists focus their energy where it will have the greatest impact rather than spreading resources thinly across many initiatives. These ideas are important for salespeople because the most powerful forms o

"The Challenger Sale" advocates for an assertive approach to sales based on teaching customers something valuable that leads them to want what your product offers, tailoring messages to different stakeholders, and taking control of the sales process. This approach stands in contrast to traditional sales approaches that are focused on building personal relationships or asking questions to uncover needs. The Challenger Sale's key insight is that success is as much about provi

Miller and Heiman's "The New Strategic Selling" argues that success in selling to large organizations comes down to building a coalition in favor of a purchase by speaking to the specific interests of each member of the buying committee. This book is useful for sales reps seeking to sell to complex organizations because it provides a framework for understanding how to persuade different types of buyers. The Four Buying Influences in the Complex Sale Complex sales involve mul

What's a really practical way to shorten sales cycles? No, don't put a gun to your sales team's head. Instead, give them a deal guide!...

The easiest way for a startup to SABOTAGE its revenue plan is by hiring fool's gold reps. These are reps who look good but aren't. Here...

One way startups light money on fire is to hire new sales reps but not set them up to succeed. One key point of failure: Training new...

What if we stopped advising sales reps to "tell a story" with their demos and instead told them to get organized? 1. Here's what you...

How will you retain the revenue you close - and avoid having your sales and CS teams kill each other? The issue is post-sale handoffs....

What's the best way to make deals close at the end of the quarter? Do excellent discovery at the beginning of the quarter. Throw away...

What's the best way to structure a demo? Be a little OCD about keeping your demo organized and split it up into sections based on...

If you run a sub $10MM ARR startup and think you can recruit talented, experienced salespeople with your vision to change the world,...

Product people think you should offer free trials at the beginning of a sales process. Traditional salespeople say: "Wait till the end."...

What's the most fundamental negotiating mistake? Not knowing what you want. Well, of course you know what you want. You want EVERYTHING....

Probably half of startup VPs of sales fail in their first year. The reason isn't what you think. It's not about hiring the wrong VP of...

What if the way I’ve always thought about sales isn’t the only way… or even the right way? I’ve been reflecting on some conversations...

Success can be a trap. Lots of startups deliver bad sales conversations because they use material that WORKED in another context. Here...

Feeling behind on revenue after last quarter? Lots of you hired new reps last quarter and are hoping they'll deliver - if they don't,...