How to Do Sales Outreach the Right Way with Aaron Ross

At one point or another, everyone does outbound sales. Facebook, SurveyMonkey, Marketo – some of the companies with the largest inbound funnels in history – have all built outbound sales teams.

Simply put, outbound prospecting can be a very predictable way to create sales appointments. And if you can create predictable sales appointments, you can create predictable revenue. Outbound is that powerful a force.

But although outbound sales is a prevalent – omnipresent, even – force in today’s sales landscape, that doesn’t mean every business should run out and establish an outbound org straight away.

You have to be ready first.

“It’s all about being at the right stage – you have something to sell. Typically, that means you have to have about 10 paying customers because that amount gives you data on who to go after, so you can nail your niche,” says Aaron Ross, on a recent edition of The Startup Circle.

“It also helps to have a deal size of about $20K annually, or lifetime contract value. Basically, as long as you have a profitable sale, you can make money in outbound.”

The right market, with the right numbers

Another critical element to getting an outbound machine off the ground is being in a market that isn’t incredibly commoditized (web design, for instance, is incredibly commoditized). It’s hard to stand out amongst the noise.

Also, a vertical like web design, or other services, can make quantifying the benefits of the service challenge. For instance, a web design firm may “make your website look better,” but that’s a soft value proposition. If you’re emailing prospects cold, you have a very short period of time (mere seconds), and you need numbers to bolster your messaging.

“Make your website pretty’ is a challenging value proposition. It is not impossible, but it makes things much harder. So, quantify as much as you can,” says Aaron.

“We call it concrete details, or tangible results. Remember, they don’t know you, they have no frame of reference, these aren’t referrals. So, be specific, and talk in the language of the people you are selling to.”

Numbers aren’t all created equal, however. For instance, Aaron suggests avoiding percentages, as they can be hard to interpret. So, avoid sentences such as “we grow our customers’ revenue by 20%” and instead use more concrete descriptions like “we grow our customers” revenues by $300,000.”

“Keep that in mind. Those numbers are stark, and concrete,” adds Ross.

“Any kind of tangible thing that tells the prospect exactly what you do, is best.”

Important signals on the road to growth

One of the clues that you nailed a niche is that you are closing customers that weren’t referrals. Customers are finding you, somehow, and your product and service have stood on its own. Once you get at least 10 of those customers, you can start putting money into marketing and sales to grow.

When you’re an early stage company, you just need customers – 5, 10, 50, whatever. You’re just a beta test at that point. Some of your early customers will work well, and some won’t. That’s not bad: now you know who is great, and who isn’t.

Of course, you want more of the great. But you can always ask how you can be smarter about getting the next 50. You’ll want to make sure there are less horrible customers in the next group. This kind of focus helps you nail your niche, and helps you hone in on what’s important. you should focus on.

From that point, your sales teams can start to specialize. That is a huge development for an outbound team.

Typically, early outbound sales teams go through four distinct periods of growth:

  • First, you bring on a junior salesperson to take over appointment setting for company leadership (typically, the CEO);
  • Then, you either hire a salesperson or another junior person (if you choose to promote your first junior person);
  • Then, you grow the team to two closers and two junior people;
  • Finally, you hire a director of sales.

“Don’t hire an executive too soon,” adds Aaron.

“There just isn’t enough there right away.”

(Editor’s note: we chatted with veteran sales leader Bill Binch, Chief Revenue Officer at Pendo, about how to grow your sales team efficiently, and effectively. You can read about our chat here, or listen to the entire podcast here.)

Outsourcing options

When evaluating or determining whether you want to outsource It’s important to decide how simple you want to keep your company. If you want to keep it simple, then outsourcing will work. If you are venture-backed, outsource can be an interim step, before getting your own team in-house.

If you go with an outsourced option, learn how those prospecting companies do their prospecting. Is it email-based? Or, do they specialize on the phones? Understand their specialties, and ensure it maps to your vertical. If you are selling to enterprise, for instance, email specialists will likely work better.

(Editor’s note: Learn more about Sales Prospecting, and how to succeed at it, in this Guide.)

And, remember, this takes a while. Commit for a year to see the results, if you dabble, you can learn something, but you won’t make any money from it.

“Getting to revenue can take 6, 9, 12 months. This depends on sales cycles. If you have a 6-month sales cycle, you won’t see revenue in 4 months,” says Aaron.

“This sounds obvious, but when you’re in a panic, and desperate, it is important to understand this. Outbound takes time to build.”

This interview was part of’s live Q&As where entrepreneurs can connect with successful founders and experts, ask questions and gets answers that they can apply to move their businesses forward. Access previous sessions and join future ones at

(Editor’s note: we’ve written extensively on the importance of understanding the ramp-up time needed for effective outbound. Recently, our co-CEO Collin Stewart wrote this piece on “investing in the journey of outbound sales.”)

Want to get started with Outbound today? Get in touch with our team.



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