[Seminar Recap] – Building a Powerful Sales Engine

Wednesday’s seminar with Craig Wortmann, CEO of Sales Engine, and professor of Entrepreneurial Selling at The University of Chicago, was our best attended webinar to date! If you missed it, make a priority to watch a recording of the chat by clicking here.

Building A Powerful Sales Engine

We had a lot of questions from our audience, and since we weren’t able to answer all of them in the time allotted, Craig and I will do our best to answer them here.

As a refresher, during the online seminar, we discussed some of the most pressing questions that sales leaders should start thinking about if they are looking to build or sustain a powerful sales organization. Among our discussion, we covered several subjects including:

  • The 3 most crucial sales challenges of today

  • What happens to the sales department in 2020

  • An Art vs. Science sales debate

  • Why sales productivity can be lacking

So here we go. Here are our best answers to questions the audience had.

1. In regards to smaller sales organizations, how much time should be spent on one item in the pipeline (prospecting, proposals, negotiation) before going to the next stage?


Craig: Here’s an unexpected way to think about this:  Think about “closing.”  When I teach “closing,” I always say that “closing is the natural outcome of a sales process done well.”  Period.  It’s not a trick.  It’s not a “technique.”  In fact, if you sell really well throughout the process, your prospects will most often close themselves.

The reason I mention this in the answer to this question is that I think that it is true of any step in the sales process. My “Entrepreneurial Selling Process” has 6 steps: Lead Generation. Qualifying. Determining Fit. Proposing. Closing. Re-setting Expectations. For each of these steps, you “earn the right” to move to the next. You don’t leave “qualifying” until you have answered all of your qualifying questions (budget, timeline, decision-maker, etc). If your prospect is resisting you in any of these steps, you bear down and get the answers you need, even at risk of losing the deal. Better to lose now than lose later.

2. Will we get to a point where everyone in the company is technically in sales? (especially in startups)


Craig: Yes and no. Everyone should have at the tip of their tongue what I call the “Art of Conversation.”  That is, the way to quickly engage someone in a conversation about what you do and why it’s differentiated and powerful. Everyone can learn to do this and then cleanly hand-off to a salesperson. And everyone should. But that’s where my expectations end. I don’t expect the software engineers to go deep into the sales process, just as they wouldn’t ask you to code in Java. But, they should be equipped with the conversation model, and they should be trained to say; “That’s a great question that I don’t know the answer to. I would love to introduce you to my colleague Jenny who can walk you through that.  Would that be okay with you?”

3. How does the length of the sales cycle affect your perspective on the selling process? For example, 1 month versus a 3 year cycle.


Craig: It doesn’t. Whether it’s 3 years or 3 days, you still have to be crystal clear about the steps you are taking with your prospect. I plead with salespeople to be explicit about their process. This builds confidence and trust. There is nothing whatsoever wrong with literally saying to a prospect; “This has been a great discussion. What is clear to me is that we are moving into what I call “determining fit” where we understand whether what I’ve got to offer matches your needs. Is that consistent with how you feel at this point?”  If they say no, you must continue qualifying. If yes, move ahead! People like to know where they stand…it’s not a mystery that we are selling something, and the more we make it mysterious the more dumb assumptions get made that come back to bite us in the ass.

4. Craig said he can teach the art of selling. How so?


Craig: The “art” of selling happens in the many “little” decisions you make meeting-by-meeting and day-by-day. What is your answer when someone asks you “What do you do?”  Do you have a crisp, interesting and short answer? Most people actually don’t. This may sound more like science, but there’s a ton of art in this. Just as big brands spend millions of dollars figuring out short slogans and taglines for their companies and products, we as salespeople need to be incredibly concise and clear. This is harder than it looks, and thus I call this art.

Another way we teach the art of selling is through practice. Every great artist has practiced for hours and hours, years and years. By practicing, say, handling objections, we begin to learn how our body language affects the prospect, what to say when, how to ask the right question at the right time, or tell the right story.  This is art.

Finally, think of the last presentation you gave. The agendas, the projector, your slides, the seating arrangement…those are all science. But they mean nothing compared to your ability to perform well and engage the audience. Science hits you in the head. Art hits you in the heart.

5. Regarding sales specialization, do you run the risk of not creating and building the relationship?


Craig: Yes, you do.  As I said in the webinar, hand-offs are absolutely key. One of the best ways to handle this and mitigate your risk of messing up relationships is to have an explicit (there’s that word again) conversation very early with your prospect that goes something like this; “Brian, I know we are early in our relationship, but I want to walk you through how we work with clients like you. We think we’ve found a way to do our work with you that really makes sense. You, of course, will be the judge of this, but let me share with you who does what in our process. Then, I’d love to ask you some questions about whether this will work for you. How does that sound?” I think if you hit these things head-on, you lower your risk with each and every hand-off you execute.

6. Is there a SaaS company sales team you would point to as an example of doing it right in the SMB space?


Brian: A couple come to mind. But one of the bigger brands that is now targeting enterprise customers as well as SMB is Hubspot. Here are a few reasons why I think they are doing it right:

Each sales rep is really a consultant of the industry and product – As a consumer, I’m self-educated. I understand the benefits, pricing, features, etc but want I need is someone who understands the inbound marketing industry more than any blog post I can find. I have this feeling when I call or inquire into Hubspot and I’m getting an answer from someone I can learn something from, not my own account manager, my own consultant/advisor.

Smooth on-boarding process – Weekly sales calls to go over specific features of the product and any questions I have in the first few weeks of usage. Always available via phone, email or chat.

Territory vs Buyer Persona – They have realized that relationships, not territories close deals. In this regard, sales teams are organized by the buyer persona they are targeting, not geographic region.

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