The Sales Coach: Chris Ortolano

Welcome to the fourth installment in our Sales Coach series. This month we’re featuring Chris Ortolano, a sales leader training reps to think like buyers. Chris is the co-president of AA-ISP‘s Portland chapter, co-founder of the Sales Stack global Slack community, and Sales Productivity Partner at Outbound Edge.

Click the video below to hear a bit about what Chris is going to share in today’s interview.


Tell us about your sales story? How did you get into sales?

I was hired by a telecom early on. They gave us two months of training, oriented around consultative sales. I was in a call center and learned it wasn’t hard to start a conversation to get other people talking. I’d use their words to help them understand how their life could be better using our products and services, and we got continuous training around this. It was great.

My next role was for a tech startup, where we were writing code, doing tech support, and selling all at the same time. It taught me about listening to the buyer, in a very discreet manner, in a more B2B environment.


It seems to me like you may be a marketing professional in sales clothing. Is the work you are doing focused on pushing salespeople closer to a marketing mindset?

I am developing an academy called SalesStack Skilljar, which brings the buyer journey and the sales process closer together. I see the sales development role as a marketing function. One issue I see is development reps are asking for meetings right away, forcing a fight-or-flight function in the buyer, pushing them away from your brand.

In the old days, mass marketers used a model called AIDA, which said a slow nurture would generate interest and trigger a response. I don’t think this has changed. If I want to learn about a brand, the first thing I do is consume the content online. A Revenue Development Representative represents the alignment of sales and marketing at the top of the funnel, focused on the buyer’s journey. It’s the heart and soul of what we teach in Skilljar.


What tips do you have for identifying buying committee members? What is an actionable thing an SDR can do to better understand their buying committee?

SDRs need to walk down the hall. If you’re not working near an account executive, you need to go talk to them and figure out who is involved in the closed deals. Get a list of technical, economic, and user buyers. They all have different needs and workflows, and different ways they are measured.

Then, go further down the hall, talk to your customer success teams, and get real stories of people using your product and the kinds of things they accomplish with it. Buyers remember these stories more than facts and figures.

For the most part, reps have the stories, but they don’t communicate them in their emails. When reps they tell me how excited their customers are, I move to the edge of my chair. It works.


Many startup sales organizations struggle with the handoff between SDR and AE. To you, what is a good indicator of where a contact or a lead is considered qualified?

SDRs are recent college grads, or folks with 1 -2 years of experience. You’re asking them to communicate with people with decades of experience. Experienced folks want engaging conversations. They aren’t looking for meetings, but you’re comping your reps on meetings.

Elevate introductory conversations by focusing on two things:

1.  Have a modicum of domain knowledge.

2.  Have a modicum of business acumen.

This knowledge creates an Account Development Rep. The ADR has the capacity to develop broader conversations, leading to deeper discovery and more relevant meetings, as opposed to just filling a calendar.

Granted, this all depends on the product, the industry, and the competition. If you’re in a B2B SaaS environment and it’s a complex sale, do yourself a favor and give your reps the ability and training to engage in conversations that make a really good first impression.


If I sat down with a team of SDRs, and gave them a list of things you expect them to do based on your training materials, they might say “This is not my job, I’m not a marketer.” What is your response?

Focus on two things. First: Who is your buyer and what do they need to know about you and your company? Second: What do you need to know about your buyer?

These are the two critical questions we all need to answer. If you don’t care enough to put attention into your buyers, why should they care to take time with you?

The best SDRs in the U.S. are working 50 hours a week on the job and 10 to 15 hours on their own, honing their skills. If you’re not one of those people, maybe sales isn’t for you. It’s not 9-5.

You can develop a buyer’s persona in about four hours, not four weeks. A/B test content. Don’t ask your reps to write content. Give them the best templates management can come up with, then give them parameters to personalize within this context.


How do you scale creating connections between customers, sales, marketing, and customer success teams to help better understand the buyer journey?

I would ask your marketing team what assets they have associated with a buyer’s persona. Then ask your sales team. Then ask your success team. This information is usually in disparate places. Bring everyone together and get it all on the whiteboard. Figure out how each team understands the buyer and then decide what is right based on your buyer.

Be united around who your persona buyer is.


Understanding a buyer persona, in this example, is a bottom-up exercise. What about when we’re being pushed into a new market, and being driven to a buyer persona from the top down?

If you study Steve Blank, he’s the guru for client development. What he suggests, once you develop a product and think you have product-market fit, is to talk to potential customers to find what their needs are without selling them. Start here to verify you’re headed in the right direction.


Any final thoughts?

Empower your reps. Don’t just hire them and give them two weeks of training. Give them continuous training. In addition, I am the co-founder of the SalesStack Slack channel – any reps that are interested in joining our growing community are welcome to contact me about joining.


Thanks so much for your time, Chris! That’s it for this time, folks. Check back next month when we interview yet another sales leader.

In the meantime, make sure to download our free e-book – Good Sales vs. Bad Sales – or click the button below to learn how the world’s leading personalized selling platform can help your business accelerate sales and increase revenue.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google photo

You are commenting using your Google account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s