How Mark Kosoglow’s Sales Team at Outreach Uncovers the Pain Points and Needs of Their Customers

Collin Stewart, CEO

4 July 2018

As any good treasure hunter or pirate will tell you, simply reaching the all-important “X” on the map isn’t the end of the line. You want to uncover the treasure.

It’s time to start digging.

This fabled process – dreamt of, written about, and tried by many – is a lot like the sales cycle: you chart a path and follow the information provided by the prospect, until you reach a place where you understand what they need and how you can help.

It’s at that point that you also start digging to uncover the treasure – the close.

Customer engagement juggernaut Outreach – a tool used by countless sales teams, amongst other departments – uses this treasure hunting template as the blueprint for it’s discovery process. Sales teams hunt for their prospect’s pain points (the X) and, when they find them, they illustrate how they relieve that pain. They paint a picture of what life with Outreach is like, and create an incurable need for their product.

“We want our salespeople to create demand, once we know they can interface with our solution,” says Mark Kosoglow, VP of Sales at Outreach, on a recent edition of The Predictable Revenue Podcast.

“We really believe that salespeople create the demand, not just recognize that the demand exists.”

Ask and ye shall receive

Unlike many sales teams that use SDRs to handle a sizable chunk of the discovery phase, Outreach engages it’s Account Executives very early in the process. According to Kosoglow, Outreach SDRs spend only a little time with the prospect to ensure they meet the minimum technical requirements (they use either Gmail or Exchange as their email providers, for instance).

That means AEs often get on calls with prospects knowing little of the company they are speaking with. But, Kosoglow adds, that near-blank slate allows for AEs to ask specific questions from the outset, and hone in topics they know will yield important information for the rest of the sales cycle.

“The process starts for us at an acknowledgement of why the meeting is happening. Basically, we just ask: ‘you are a busy sales leader, why did you take this meeting with us?’ We really try and make sure they understand why they are on the call,” says Kosoglow.

“And, we make sure to include the fact that we used Outreach to book the call, so this becomes a real world example of how Outreach works.”

From there, AEs probe to find the prospect’s particular “X” – pain points such as how long it takes to respond to an inbound lead, or how many accounts an SDR can prospect to without Outreach – by asking questions about their organization.

Some of those questions might be:

  • What sales roles do they have?
  • Is it full sales cycle?
  • Are the hiring new sales team members?
  • Are they an inbound focused organization?
  • Or, do they do more outbound?
  • And, who handles the upsell and resell processes?

“We want to know their systems – how do they reach out? How do they get in contact? And, how do they move leads along the sales funnel? And then we offer where we can help,” says Kosoglow.

“This is all to find that “X.”

Once they’ve landed on a pain point, Outreach reps start digging by asking targeted questions around that pain point. For example, if the pain point is that it takes the inbound sales team too long to respond to the volume of inbound requests, an Outreach rep will ask questions such as: ‘what do you mean your reps are too slow?’ Or, ‘what are the specific challenges you face because your reps struggle to handle the volume of leads coming in?’

Those questions will yield concrete examples of what the prospect is dealing with, and will allow the sales rep to show exactly how Outreach can help and build demand for the product.

Diagnose and confirm

Along the sales process, most, if not all, good salespeople are trained to pause and check to make sure they’re digesting the avalanche of information coming at them. The trouble is, often that pause comes with a all-too-simple questions like: ‘does that make sense?’ Or,’are you following along?’

Those questions invariably produce a simple answer: ‘yes.’ No one wants to admit they don’t understand, or they aren’t following as closely as they should be. Of course, either could scenario could be true – who among us hasn’t been confused? – and a sales rep would surely benefit from knowing that.

To make sure there are no misunderstandings, Outreach reps use a method called “diagnose and confirm,” where they repeat what the prospect has told them, and then confirm if they’ve gotten it right. This is a shrewd tactic because it elicits a response, regardless of whether the rep is right or has misunderstood what the prospect has shared over the course of the call.

“Diagnose and confirm helps to correct information, and get new information. If they say yes, they often continue to share more information,” says Kosoglow.

“Or, they correct you and, again, share information about their company. It’s great.”

We can’t forget, adds Kosoglow, that throughout the sales cycle, the prospect is digesting a lot of information, and building an inner narrative based on what they’re hearing and seeing. But no matter how hard the sales rep tries, or skilled they are, they can’t be sure the inner narrative the prospect is building is the right one. So it’s critical to use approaches like “diagnose and confirm” to get a window into what the prospect is thinking, and to keep everyone on the same page.

It may take some coaching on the part of the sales leader to break the habit of asking too simple questions during sales calls, but it will help ensure your discovery process goes as you want. And if your discovery goes well, you’ll better understand how you can help your customers.

“Good sales is building understanding that goes back and forth. We’re trying to understand each other. So when a prospect throws the ball to you, just throw it back. Just ask questions,” says Kosoglow.

“Don’t worry about saying the perfect thing. Just listen to your sales instincts.”

For more on Kosoglow’s thoughts on the discovery process, and how Outreach reps connect with prospects, check out his full interview on the The Predictable Revenue Podcast.