EPISODE 693: Fixing a Dry Sales Pipeline with Monica Stewart

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Today’s show featured an interview with business consultant Monica Stewart.

Find Monica on LinkedIn.

MONICA’S TIP:  “Treat your role and your own book of business just like a consultant would. If you’re stuck in Q1 and you’re saying, “I don’t know how I’m going to get to my number,” don’t just think like, “I need to sell more,” really start to break it down. “Do I have the right people in my pipeline, and do I have a good way of getting more of the right people in my pipeline?” Then once they’re in there, “Am I really doing a good job at moving them through the process that they need to go to?”

THE PODCAST BEGINS HERE

Fred Diamond: Today, we’re talking to Monica Stewart. This is the Sales Story and a Tip Podcast. I’m excited to talk to you, Monica. Tell us a little bit about yourself in under 30 seconds and let’s get started with your story.

Monica Stewart: Thanks, Fred. I’m excited to be here. My name’s Monica Stewart. I’m the founder of MSP Consulting. I help startup founders with an ARR of between 2 to 10 million get to the next phase in their growth. I’ve been doing this for 15 years and really excited to be here today.

Fred Diamond: By the way, you’re in Mexico City right now as we’re doing the interview. That must be exciting to be down there.

Monica Stewart: Yeah, it really is. I spend about half the year here. For those of you that are watching this on YouTube, you can see my beautiful jungle plants behind me. It’s such a cool benefit of running your own business, that you can create that kind of flexibility.

Fred Diamond: Let’s get to it. Monica Stewart, tell us your sales story.

Monica Stewart: This was about six years ago. This was a company that I was working with when I first started my own consulting practice. They’re in a very specialized industry, and they really knew their market super well. They had developed something that filled a real need for a very specific niche.

When they came to me, they were like, “Monica, we just need help with our sales.”

I was like, “Okay. Well, what do you mean?”

They’re like, “We can’t sell anything and we feel like we should be able to do that. We just need help with sales overall, and you seem like you’re really good at that. Can you just come in and fix sales for us?”

I was like, “Well, that’s not really a plan, but let’s see what we can figure out here.”

I should say that nobody on the founding team had any sales experience. They had industry experience, which I think is the case with a lot of really smart founders. They had two salespeople and half of an SDR that was also doing operations.

I go in and I start talking to everybody and I start looking at their CRM. I sit down with the sales team and they’re like, “You see, Monica, the problem is, is that we just don’t have anyone else to sell to anymore. That’s it. We’ve called everybody in the CRM, and some of them said yes, but everyone else has already said no, so we’re done.”

I was like, “Wait, what? You’re telling me that your company is three years old and you’ve reached the end of your lifecycle already?”

They were like, “Yeah, our market is just really specific and that’s all there is, there’s nothing left for us to do.”

For anybody that’s ever been in a startup selling environment, you might have recognized that obviously this point never actually happens to anybody. What I realized is that in the absence of having any kind of objective way to evaluate their sales process or where they were in their go-to market journey, everybody in the company was basically just looking at what was right in front of them, and they were saying, “Well, this is the problem.”

For the sales team, they were having this experience where they were coming into work every day and they were calling everybody in the CRM and they’re like, “Well, we talked to that guy three months ago and he said no, so that’s done. There’s nobody else. That’s the problem.” Then if you talked to the product team, they were like, “Well, the product’s just not where it needs to be, and that’s the problem.” Then if you talked to the half the SDR, he was like, “Well, we’re not getting any leads.” Then if you talked to the CEO, he’s like, “It’s because people just don’t understand my vision.” When they talked about how are we going to move forward as an organization, it was almost impossible to do that because everybody was talking about a totally different thing.

What we did is we just went down the list and we were like, “Let’s look at all the different parts of your team. Let’s talk about who you’re selling to. Do we know who those people are? Let’s talk about where you’re getting your leads from,” their lead channels, they had two of them. That was obviously an area that we could improve on. Once you’re getting people in the door, what are the conversations that you’re having with them? How effectively are you closing them? Actually, with this company, that was a big thing that we were able to do. We found that it was taking them four times as long to lose a deal as it was for them to win a deal. They were just letting people stay in trials for months and months.

Then it comes down to once you close somebody, then what are you doing with those customers? Are you onboarding them efficiently? Do you have a process for that? Then also let’s look at the team. Do we have the right people in the right seats? Do they know what their job is? Do they have the tools that they need to do that job effectively?

Then once we started breaking it down into those categories, some patterns emerged and we were able to say, “Here are probably the things that we need to fix. You guys need to get some new lead data. You are actually not talking to the right people. You’re talking to companies that are way smaller than the ones that you should be talking to. If you’re talking to bigger companies, you’re talking to the wrong people at those companies. You’re taking a no from people who actually can’t say yes. That’s a problem that we can solve.”

Then from the team perspective, a very typical startup scenario, they were like, “Great, let’s hire some salespeople that have done sales before. Then they’ll come in and they’ll be able to do sales here, because that’s how that works.” Well, that’s not how that works. You need to understand how to sell that product to that persona at that company. Once we started to pick apart this problem of fixing sales, then we were able to start making progress on these individual threads. Then the whole train started to move forward in a different direction.

I would say that what I want people to take away from that is that if you don’t have an objective standard for every single part of your organization, you’re always going to end up in this scenario where people are just going to look at what’s right in front of them and they’re going to say, “This is the problem. We need to fix the product. We need more leads. People don’t understand my vision. Marketing is broken,” whatever it is. You’re like the fable of the people in the dark and each one of them can only see one part of the elephant. What I would really recommend people to do is find a system for benchmarking where your organization should be across different categories at different stages of your growth, and then regularly refer back to that. That’s going to help you figure out the roadmap that you can use to get yourself unstuck when you run into problems like that.

Fred Diamond: So many things to unpack there. One that stuck me through was taking a no from somebody who can’t say yes. So many times, not just with small companies, but large companies as well, they’re not just talking to the wrong people, but they’re talking to people who aren’t involved in the decision. You talked about the word fable or parable before, we always talk about how great the first meeting is, because every first meeting is great. The customer is talking to someone about an idea, they get to talk about their problems, and every sales rep is like, “This went great. It’s a 50% chance that we’re going to get it.” Try getting the second meeting, that’s where the rubber meets the road, and then of course, the third and the fourth.

You started to allude down this path, but what’s one tip that you would tell salespeople listening to today’s Sales Story and a Tip show that they need to implement right now that you definitely walked away with?

Monica Stewart: I would say that for individual salespeople listening to this show, you should treat your role and treat your own book of business just like a consultant would, just like I did coming in and evaluating an entire organization. If you’re stuck in Q1 and you’re like, “I don’t know how I’m going to get to my number,” don’t just think like, “I need to sell more,” really start to break it down. Like, “Do I have the right people in my pipeline and do I have a good way of getting more of the right people in my pipeline?” Then once they’re in there, “Am I really doing a good job at moving them through the process that they need to go to? Then am I doing a good job of showing them a path to implementation and are there maybe some areas where I can level up my skills to be more effective at all of those stages?”

Fred Diamond: I like what you also said before where they said, “We just need to hire some salespeople.”

Monica Stewart: Yeah, and have them do the sales thing.

Fred Diamond: There’s a lot of great salespeople out there, of course, but they’re good at selling something to somebody. They know the public sector market, or financial services, or aviation, whatever it is, and they’re good at selling a particular solution. Maybe they can move over and sell a similar solution to the same customer. I remember when I was applying for one of my first sales jobs, the VP I interviewed said, “I want one of two people. I want someone who could sell the same thing to different customers or that could sell a different thing to the same customers that they’ve been selling for the last 10, 15, 20 years in their careers.” The notion that a great salesperson can sell ice to igloos is not true, especially now where the customer is in charge. Especially when you’re going higher up with a higher, more valued solution, you need professionals who know the marketplace, who know the trends, who understand where the market’s going, who understand how the customer buys, et cetera.

This has been fascinating. I want to thank Monica Stewart. She was a guest on today’s Sales Story and a Tip Podcast. Thanks Monica.

Transcribed by Mariana Badillo

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