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Startup Sales Advice For Technical Founders

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Sales advice from Glengarry Glen Ross

Sales advice from Glengarry Glen Ross

Sales, sometimes, gets a bad rap. Many of the quintessential sales-oriented movies often showcase a misleading representation of what it’s like to sell something. Movies like Boiler Room and Glengarry Glen Ross show pushy sales reps who will stop at nothing to make the sale. They’ll ignore customer objections and continuously push their own agenda. It’s often accepted that being a smooth talker will land you that sale. But sales is more about being a smooth listener than a smooth talker. I wanted to share a few lessons I’ve learned the hard way that I wish I could have taught my younger self:

Stop Assuming and Start Listening

Sales techniques are sometimes misrepresented as brute-force persistence. The constant phone calls, email follow-ups, up-selling, aggressive pricing methods create a sense of bullying to sell something. But to me, a sales rep is like a detective trying to understand exactly how his solution fits into the picture. Don’t make any assumptions about what the customer needs, you should be looking for just the facts. Without being disrespectful, you need to find the answers to questions like:

  1. Why are you looking for a solution?
  2. Do you have a budget for a solution?
  3. Do you have authority to purchase a solution?
  4. When do you need a solution?

The best thing a sales rep can do to make a deal happen is to listen. Listen to your customers when they complain, listen to them when they ask questions, listen to them when they give praise. Even if customers don’t directly tell you what they need, if you read between the lines, you’ll find everything you need to know. There’s no need to guess what your customers want, they’ll tell you, if you’re willing to listen.

Timing is Everything

Timing is critical for parties on both sides of the table. For customers, they want to play the field and line up solutions from different competitors. For sales reps, too much information at once leads to unfocused deal discussions while, on the flip side, too little information results in customer disinterest. Knowing the right time to discuss certain topics is more art than science, but there are a few rules to loosely follow:

  1. First, identify and fully understand customer need
  2. Then, find the decision makers
  3. Then, demonstrate value of your solution to decision makers
  4. Finally, negotiate price point

There is a time and place for each of these steps and if you skip around, you’ll likely find yourself wasting a lot of time going backwards and re-doing parts of the sales cycle. I once made the mistake of pitching to a room that was missing a key decision-maker and I, ultimately, had to schedule another meeting with him just to do the exact same pitch. It was a waste of my time and delayed the entire sales process.

Know The Value Of Your Solution

For younger companies that don’t yet have an established pricing model, it’s too common to see them giving away a solution for much lower than its worth. Try to quantify the ROI for your customers and price your solution accordingly. Discounts should be a last resort and, even then, if that’s the only way you can compete with other solutions, you need to rethink your strategy. If you are a startup and your price is your only competitive advantage, that is a clear sign that your product is not differentiated enough from already existing products. And as a startup with severely limited resources, you will always lose this situation. If your product is 10x better than existing solutions, you should be able to charge 10x more. Discounts are a non-issue when your product is that much better.


I’ve made a lot of mistakes learning these lessons and I hope people new at sales can learn from them. Just like everything else, sales requires lots of practice and eventually, you’ll be able to manage every step of the sales cycle like a pro.

Despite being critical about sales movies, to be fair, there are movies that I think have good sales lessons in them:

Jerry Maguire – Even if you only have one client, do whatever it takes to make him happy. Customer Service will always be #1.

Lord of War – Not an uplifting story by any means, but Yuri Orlov is one hell of a sales guy. He develops strong relationships, delivers on promises and let’s his products speak for themselves. Ultimately, he sells something that people desperately need.

Author: Alvin

This is a blog about entrepreneurship, travelling, business and life from the mind of Alvin Tai.

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