Aaron Ross on the Heresy Podcast: How to Build a World Class Outbound Team

Collin Stewart, CEO

14 November 2018

And now for something completely different.

Instead of sitting down with one of the countless sales leaders building and scaling revenue teams across North America – the sheer number of inspiring sales professionals never ceases to amaze us – we thought it would be cool to share a few words from our fearless leader, Aaron Ross.

If you’re reading this, you probably already know Aaron’s story: built and scaled the original outbound prospecting team at Salesforce (a tiny Bay Area company), wrote the book on outbound sales, leads our growing team at Predictable Revenue, and busy father to 9 (that’s right, 9) kids.

Aaron recently sat down with Dimitar Stanimiroff – founder and CEO of workflow and analytics platform Heresy – to discuss all things outbound sales on Dimitar’s Heresy podcast.

Below are some of the highlights from their wide-ranging chat (note: the answers have been edited for brevity and clarity). Click here if you’d like to listen to the entire podcast.

Is the broader Predictable Revenue framework – that you pioneered at Salesforce and highlighted in the book – still as effective as it once was for outbound sales?

Part of the fame of the book came from detailing the cold emailing technique that would create predictable leads. I created the outbound team at Salesforce in 2004 / 2005, the book came out in 2010 and the world of outbound sales has been taking off since.

People are creating apps specifically for sales – it really helped create a resurgence for outbound sales. And, that’s what our business does: if you don’t have an outbound prospector, we create those leads for you. But for most companies, at some point, you need an outbound prospector.
Of course, there have been changes. More people are sending more messages. That applies to outbound sales, but also for other disciplines. For example, there is way more content marketing now than there ever was. There is just more stuff, to put it simply. There is more noise.

In today’s landscape, you probably can’t send a poorly worded email and see great results like you could 10 years ago. People tell me they get 10 of my Predictable Revenue style emails per day (with outbound prospecting you could be using cold emails, social outreach etc.) But, despite the increase in activity, we see that outbound is still very effective.

In the context of outbound, how do you cut through all of this noise? How do you make sure you’re one of the people that get through?

There’s a big piece missing from Predictable Revenue book. I didn’t know it was missing until I did From Impossible to Inevitable with Jason Lemkin years later. The first part of From Impossible was called “Nail Your Niche.” This is a critical concept to understand because you won’t grow until you nail your niche. So, when I started seeing companies struggle to grow – they aren’t getting the response rates they wanted, or they aren’t closing enough deals – most often it was because they hadn’t nailed their niche.

What this concept means is that you’re able to determine which companies need you the most, and which companies are just a nice-to-haves. For the companies that need you, you must also understand how to communicate in their language, and know what their problems and pains are.

You can get to, say, your first $5 million, or even $10 million, based on relationships, word of mouth, and brand strength. Past that, you need to be able to market and sell to people who don’t know you, and don’t know your brand. And, your message needs to resonate with people, all on its own. So, you have to find your best customer and communicate your tangible value to them.

What this looks like on a day-to-day basis is spending more time interviewing your customers to really look for more empathy (how do you put yourself in the mind of your customers?), understanding their needs and interests, and how they communicate. Most companies still talk in their own product language – “our network-scalable, integrated API” etc. – but that is not how customers talk. You need to learn the customer’s language and translate that to your outreach.

There are also a lot of companies in difficult niches. If you do professional services, custom development or have small deal sizes, outbound is much harder. It doesn’t mean outbound is impossible – it almost always works – but it is much more difficult. In those cases, it really comes down to the people you have on your team. If you have a great prospector, he or she can figure out almost anything. If you have a prospector that struggles to think for themselves, they won’t be able to do it. They can succeed in a SaaS company with an easy-to-sell product, but they won’t work in a company in a really difficult niche where you really need to know your customers, and their problems. You have to hire right, and hire better.


How do you hire and retain the best? An SDR is likely the person in the company that hears “no” the most. It can be disheartening. How can hiring supersede that?

The kind of person you’re looking for is someone right out of college, or with up to, say, 5 years of experience. This depends a bit on how complex what you do is. But, not having too much experience helps. If your SDR has been a closer before, it won’t work either. It looks like a step down to an AE, and they’ll want to be promoted quickly. It has to be a learning opportunity for the person you bring on.

The person also has to have a good head on their shoulders – they’re ambitious, they want to learn, they want to be successful, they are looking for a career in sales, and they have shown an ability to be successful in some other area of their life. This job requires you to be adaptable, and really think on your feet. Having previous success, regardless of what it was (it could be starting a non-profit in college), will really help prepare your candidates for the fast-moving nature of the job.

Sales is not rocket science. This is a job that the right candidate can pick up, if they’re smart. Closing jobs can be more complicated, of course, but this role requires hustle, and smarts. As for compensation, that varies, depending on where you live. You should offer a base salary that lets your team pay their base bills, with, maybe, a 50% variable commission in addition to that. The comp plan should be tied to qualified opportunities generated per month, and how many of those opps close every month. That basic breakdown works for about 80% of companies (it may not work if you have super short or super long sales cycles, though).

You’ve given a lot of advice, for sure, but what is the best sales advice you’ve ever been given?

That’s a great question. Two books that come to mind – both very influential in my early days at Salesforce – were Wooden (about college basketball coaching icon Jon Wooden), and The Toyota Way, which about assembly lines. I took an assembly line approach to my life in sales, that had had a lot of overlap for me.

As far as advice goes, it’s all about doing what you want to learn. Want to be in sales? Go and sell? Want to be a manager? Then, go out and manage something. If there is something you want to learn, than figure out a way to do that, whatever it is.

For more Aaron’s thoughts on building and scaling outbound sales teams, check out the rest of his interview. And, of course, check out The Predictable Revenue Podcast for more interviews with inspiring sales leaders of all stripes.