How I Became Google’s Top Performing Sales Rep in the World

Sales hacks that took me to the top of Google

Steve Benson
8 min readJan 14, 2020

When I was in school I wanted to be a consultant. So I went to the University of Wisconsin and got a B.A. Then, I went to Stanford and got an MBA. It was 2007, my path was set and I was on my way.

Fast forward two years to 2009. I was recognized as Google Enterprise’s top-performing sales rep in the world. I hit 227% of my quota for the year.

Fast forward another two years to 2011. I was named Google’s top-performing maps rep. I hit 183% of my quota that year.

But I was supposed to be a consultant, remember? So, how did I end up there?

My Path to Sales

When I was at Stanford, I was doing what most grad students do, considering various career paths. A close friend of mine, whose opinion I trusted and who had worked in consulting, told me that despite my chosen path, I probably wouldn’t enjoy consulting because it’s such independent work, and I like to interact with people.

But like a good friend, he also offered some positive advice. He told me I had the raw talent to be a great salesman.

It was eye-opening — and I listened to him.

I started out at IBM selling hardware, software, and consulting, but soon realized Software as a Service was the better market to be in. Higher margins and interesting solutions.

I landed a sales job at Google. I worked alongside some of the most talented and inspiring people I’ve ever met. One of them was Mark Flessel, my first sales manager, who taught me the most important piece of sales advice I ever learned (more on that later). It became the basis for my entire sales strategy, and by 2009 I received the previously mentioned distinction at Google.

My old college friend was right, I did have the raw material to be a great salesman. Taking his advice in that formative moment was one of the smartest decisions I’ve ever made.

After an invaluable experience at Google, I went on to start my own business, Badger Maps, a route planning app for field salespeople. We currently bring in 4 million a year, have 60 employees working across the world, and grow at 40% a year.

But I wouldn’t have made it to this point if I hadn’t learned effective selling strategies from the best. I applied those same strategies to build Badger Maps and continue to use them as part of our ongoing selling strategy.

Here are the 6 sales hacks that brought me to the top of Google (and still use to this day):

1. Find the Right Headspace

The sleazy salesman. Money hungry, untrustworthy, synonymous with poor quality products and bad deals. Sure it’s a stereotype — but everyone knows it, and loathes it. So how do you avoid being perceived as one when the pressure from your sales manager, not to mention your life, has you focused so squarely on making your quota?

The answer lies in your ability to project just the opposite: a trustworthy, enthusiastic friend, genuinely excited about solving a particular need for your prospect.

Imagine you just came back from a trip to Hawaii that you absolutely loved. When you tell your closest friends about the trip, your excitement for the experience colors everything you say. The enthusiasm sells the experience more than the amenities you describe.

The same is true of sales!

It’s important to believe in your product and be excited about your prospect and the results they will see with your solution. Just like the trip to Hawaii, your enthusiasm sells the solution more than the features you describe.

This is how you communicate value. And it’s the right mindset for selling.

The quality of your persona-positive, genuine, and trustworthy, will avoid any unfortunate stigma of a sleazy salesman.

2. Demonstrate Business Value

Earlier, I mentioned that Mark Flessel, my first sales manager at Google, gave me the best piece of sales advice I ever received.

He told me to study a prospect’s business to learn their specific KPIs and business goals.

If I knew the exact numbers and pain points that would convert my prospect, I could map out my solution to best fit their needs.

Understanding pain points is one half of the equation. Your solution must solve real problems for your prospect, thereby relieving them of pain points. But how do you demonstrate business value?

My favorite tactic was to use this phrase as a template:

“Our product does ________ , (feature) which allows you to do ________ , (benefit) and that means ________ (result) in terms of real business value.”

The beauty of this mental template is that it simplifies the cost-benefit analysis, reducing potential outcomes to a series of three connected dots. All we have to do is fill in the values, and if the final figure is greater than or equal to a prospect’s KPI — you’ve got yourself a sale!

3. Show What They Stand to Lose

Psychological studies show that people have stronger reactions to a sense of loss than to potential gains. Basically, people hate losing things more than they like gaining things. We can use this theory to our advantage in sales.

Positioning untapped ROI as a loss can be a powerful motivator on a prospect.

Let’s take for example the SaaS market environment. For many businesses or consumers, software is not necessarily something they need. Even if you demonstrate business value and a significant ROI, they may not see a need for your software when they have made do for years without it.

So how do you convince a prospect that they need your service? You position inaction as a loss.

Take the same calculation of their ROI, and position the figure as a cash amount they are currently losing by not having your solution in place. The logic posits the ROI of your solution as a true indication of what their business should be making. Therefore, anything less is not just nonsensical, it’s a loss of revenue.

4. Anticipate Price Objections

We may dream of sales processes free of objections, absolutely frictionless from qualified lead to commission check. But in reality, objections are just a natural part of the process. That being said, we want to mitigate objections where possible by addressing the factors we can control.

One such factor is price.

Interestingly, no other factor has the potential to block a sale as quickly. Price objections can elicit emotional responses, and when looking for a smooth process, the last thing you want is confrontation of any sort. To avoid any such issues, be proactive — Address the cost before your prospect does. To do this, during your presentation, just bring up the price by saying something like, “People often want to know why our product is more expensive than some of our competitors, and that’s because it’s the solution that creates the most value for our customers — Let me show you how.”

This does a couple of things for you strategically:

  • It gives you ownership of the issue. It’s an opportunity to state the price outright and provide a brief explanation. Aim to get a confirmation from your prospect that the cost is reasonable. That way you can fall back on it later if an objection comes up.
  • It also helps you validate your customers' concerns by bringing up something that was on their mind, and this builds trust. By discussing price without prompt, you are consciously demonstrating to your prospect that you understand their concerns. And understanding is the bedrock of trust.

This doesn’t just work with price, it’s important to note that bringing up common objections to your solution before your customer does is often the best way to overcome any objection.

5. Uncover the True Objection

Subtle avoidance, vaguery, hollow assurances that they’ll think about it. There is a myriad of ways prospects can shirk your efforts, delay progress, and ultimately let a sale go cold. If your prospect seems to be side-stepping, consider a direct approach.

Imagine asking a series of simple questions to gauge their interest. “Are you interested but not sure? Or just not interested? Which is it?”

This may sound overly simple or too direct, but this question will provide you with one of two actionable results.

  1. If the prospect is in fact not interested, you can walk away. There’s no need to waste your time.
  2. If the prospect is not sure, you have an opportunity to extract the true objection.

You have likely failed to demonstrate business value, cover a key issue, or resolve a previous objection. Ask specifically what they’re unsure about — their answer will likely be related to fit, function, or finance. Any information they give up allows you to re-engage.

A stalled sales process yields no results. I call this the “Which Is It?” method, and it gets the ball rolling.

6. Ask How to Follow Up

Salespeople tend to be in-tune, self-aware people with good social skills. So it’s no surprise they often worry about annoying their prospects with too many follow-ups.

The fact is, 80% of sales require 5 follow-ups or more. They are necessary, and can even be enjoyable for your prospect when done with intelligence and tact.

The most important tip I have for you about the follow-up is to ask your prospect what works best for them at the end of your initial sales meeting or phone call. This will give you the exact time and method they prefer, and their permission to keep in touch. Learning this upfront helps you avoid ever being an annoyance to your prospect.

To stay relevant and engaging, try to mix up your methods, provide useful material, and develop a personal relationship with your prospects. Your messages should be associated with great value to increase engagement.

A great follow-up strategy is a simple triad of content, approach, and timing.

Asking the right questions from the beginning will let you follow up with confidence.

Giving Back

I based my personal selling strategy on advice I got from the best. As CEO of Badger Maps, I make it a priority to not only share these tips with my sales team but with our customers: fellow salespeople.

To be a successful salesperson, you have to do more than scratch the surface of the sales process. My aim here is to give you tips that dig deeper. Tips I learned inside one of the best companies on the planet. Tips you can apply to your current sales job.

For more sales tips and coaching, check out my podcast Outside Sales Talk, my video series for salespeople, Training Tuesdays, or connect with me on LinkedIn.

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Steve Benson

Field Sales Expert & Speaker. Host of Outside Sales Talk Podcast. CEO, Founder @ Badger Maps