Hack & Hustle

How to ask powerful sales questions

Everybody who wants to be great at sales needs to master one skill: the art of listening. The better you become at listening, the more you sell.

But don't be the passive listener whom the prospect uses like a psychotherapist - babbling on about whatever he wants to get off his chest. Great salespeople actively direct the course of a conversation by asking astute questions.

 This sounds great in theory - but try putting it into practice, and you'll see how hard it is. Prospects quickly become uncooperative, antagonistic or flat out tell you that they don't want to answer your questions.

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500 Startups fireside chat with @Steli [video]

I recently had the honor of doing a 500 Startups fireside chat to share some sales hacks with a group of awesome founders.

Here's the recording of the event. The video quality was really low, hopefully the content will make up for it (listen with headphones). If you're wondering whether it's worth putting up with this audio quality, let me share what Christoph Janz from Point Nine Capital had to say about it :)


(If you haven't been reading his blog The Angel VC, check it out, lots of great content in there for SaaS startups.)

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This "Inception" product demo hack helps us get more customers

inception“Brilliant!” That’s what I thought when I heard Kevin sell this deal.

He was giving a product demo to a prospect, but in a way I’ve never heard of before, and it ultimately helped to make the sale.

If you're looking for ways to demo your product more effectively, keep reading.

Adapt this approach to your company and you'll transform your product demo into a sales machine.

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5 steps for startups to re-engage past demos & close lost prospects

lincolnmurphySaaSconsultantThis is a guest post by Lincoln Murphy from Sixteen Ventures. Check out his great blog on SaaS marketing, customer acquisition & churn reduction.

When it comes to sales hustle, Steli is the man. He’s taught us about the power of the follow-up and turning failed demos into sales.

Well, this powerful sales hack I’m going to share takes both of those ideas and applies it to the reality of rapid startup product evolution; in the early days, your product probably sucks… and you showed it to actual prospects!

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Optimizing self-service SaaS models... with sales reps


Self-service. Oh, show me a SaaS founder who doesn’t love self-service customers. They find your product through word of mouth, inbound marketing or partnerships. They eagerly sign up for your trial. Automatically convert into paying customers. And no member of your team needs to sell or support them. 

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5 Steps to get your first customer [webinar]

Our very own ace of sales, Kevin, recently did a webinar for early-stage startup founders. If you want to know how to get your first customer, then this is for you.

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Why sales leaders should fail in front of their team

I hate failing. I hate failing publicly even more. Yet, I do it all the time, and so should you if you’re managing a sales team.

Do you want your sales people to boldly experiment with new sales approaches, come up with creative ideas to close more deals, even if it means trying new things that might lead to failure? 

Or do you just want an army of sales lemmings, sticking to the tried and true, avoiding risk? 

If you’re in startup sales, sticking to the tried and true just means you’re slowly turning yourself into a dinosaur. You won’t survive for long in a fast-changing marketplace.

But how do you cultivate and maintain that sense of boldness? How do you create an indestructible sales team that’s willing to put themselves out there and fail?

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Systematizing sales with software and processes by @patio11


Here's a guest post from Patrick McKenzie. He published this epic piece on how to move upmarket from a low-touch sales SaaS into a more rigorous sales process back in December to his subscribers. We're sharing it with you because it's filled with smart ideas and because it shows one way of unleaching the power of our sales software for solopreneurs and small teams. If you're a developer, you should also check out Starfighter (more details below)!

Hiya guys!

Patrick McKenzie (patio11) here. You’re getting this email because you asked for my occasional thoughts on making and selling software. Today we’ll be making software to sell software — fun stuff! The goal is giving you some actionable ideas for getting the tooling and process needed to do medium touch sales, in a way which won’t make you feel like you’re hawking used cars.

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I fired half my team


One of the most difficult things I ever had to do as a CEO was to fire half of my team.

Our startup had seen months where we couldn’t keep up with demand, hired dozens and dozens of sales people, trained them... and then business went down and we had a couple of really bad months.

Firing an employee at your startup is bad enough, but firing dozens of people at the same time is a completely different animal, and I learned a lot from this experience.

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Training a new sales team? 5 ways to set them up for success

This post by Nick Persico was originally posted on CloserIQ's blog. CloserIQ is a sales career platform connecting top sales talent to startups.


If you run an early-stage startup, your first sales hires—and how you train and introduce them to your company—will set the tone for the next stage of your startup’s growth. After all, it’s likely that this will be the first time your product will be sold by someone other than you or your cofounders. It’s the first time that people without the context of your company’s history will represent you.

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