THE SECRET TO CLOSING LARGE ENTERPRISE DEALS

Everybody enjoying their sales experience? What a year it's been. It just started and now here we are. Well, I've got a great topic for you today. How do you close those bigger deals? The big deals that really make the difference. And why are they so hard? They are not just a little bit harder. It's not just the dollar amount either. It might be whether you've got a new product or an established brand. With each person in the decision path of buying the product? Not just picking the product, but buying the product.

We deal with the people who pick the product.

Are you dealing with the people who buy the product internally?

Do you know them?

Do they know you?

Do you understand what they care about? Because their opinion does matter. We, we think that if we get the person who's using it excited enough, willing to do enough that they'll buy it. And that can help, but it's rarely enough. And what we're running into is what I call the 3 times a charm trick or trap, meaning that the first time, the end of the quarter, you push through, it dies. Second time, you get the technical win, maybe they buy a little. Most likely to buy nothing. The third time they buy something. Now, the problem with that strategy or that trap is that it takes 3 times. And that's a lot of time, typically 9 months plus the original months. It's about a year. So what we really want to do is become better at it. And even if you believe sales is just a sequence of tactics, You have to execute the tactics well. And the way to do that is to practice. Brevity Pitch has just introduced Brevity Play. It is an evaluation copy of Brevity which allows you to play, practice on your phone. No username or password, no hassle. And get ready. get good at those sales conversations. So, go to brevitypitch.com. Sign up for Brevity Play and get your free copy. Here we go.

Hey Janet, thanks for joining us today. As a way of getting started, tell us a little bit about yourself.

Well, I may have taken a unique path to sales compared to some. I've been doing this for probably over 30 years. I started out in accounting and finance and found that I couldn't really sit still very well. So I, I went, transitioned into accounting and finance sales and enjoyed that, and then added on accounting, finance, distribution, manufacturing, process manufacturing, and eventually became a national sales manager. And then I went to Oracle, went to Oracle for a while, and, uh, I found that people really liked their products, but they didn't like the business practices. So I created my own business as a reseller of Oracle because the products were great, but business— they wanted to have someone wear their hat, right?

Yeah.

So I did that pretty successfully for a while, and then I actually stepped aside for 10 years and was a mom. And so that was rare to step aside. And while I stepped aside, I was an active angel investor. So what was interesting about that is I got to wear many hats. You know, I had the accounting finance background, but then suddenly I was in charge of QA because there was no staff, and I got to wear many different hats. And so I went from being a business owner to a contributor in many different areas. Oh, you need this? Suddenly I'm an expert, right? So I did that, and then once both kids got licenses, I went back to work, and I've been back at it for 8 years and having a great time. So it's kind of been a unique journey.

Yeah. Did you miss it during those years?

I honestly totally missed it.

Did you?

I really missed it. And that's why I stayed active in angel investing. But given that I've chosen technology sales as my profession, uh, technology didn't wait for me. I had to learn a lot when I came back.

It didn't stop?

No, it was just so— I remember onboarding after being off for that long going, what do I do?

Yeah.

And luckily Google was there. When I started technology sales, we did not have Google. We would go fly cross-country with a Thomas Guide.

I remember. Oh, I heard stories.

Yeah. Allegedly.

And was it your personality? Well, because accounting and finance are kind of the opposite of sales, isn't it? A little bit?

You know, it is. You know, I went to UC Berkeley and later on My first job out of college was with Hewlett-Packard, which is a great foundation. And I was on the recruiting team for UC Berkeley for HP. And one of the things I really found is everyone would say, I'm in marketing. Well, great, but what can you do? I can market. And I, I kind of walked away with the belief that you needed to have something qualitative as well as quantitative.

Yeah.

So when you're a sales engineer, really knowing the product and knowing what you're talking about, allows you to empathize and really understand the business issues. So it actually worked pretty well for me. I still, you know, to this day, I've got to deal with, you know, SOX compliance and, you know, value propositions and ROIs.

So you were selling to the finance side of the business at Oracle, or—

Um, I was selling, uh, their business applications. So, you know, IT and finance, it's the whole business many times. Yeah.

And what did you like about sales?

You know, one day you might be talking to a retailer and the next day you're talking to metallurgists. It keeps your curiosity alive. It keeps you constantly learning. And I really enjoyed that.

And how'd you become good? Because I don't meet many accountants or people in accounting that are going to be natural salespeople.

I think I had some excellent mentors.

Yeah.

And I think that, you know, certain people have taken the time. I think one, one thing everyone needs to do is we need to identify mentors and be a mentor and take the time. And, and that allows you to be a leader, even if you're not a— even if you're an individual contributor. So I had some good mentors. My father spent his entire life as a sales engineer. And went into sales management. And he taught me some pretty good foundations, you know, integrity. And, um, you don't want to sell ice cubes to an Eskimo. You want to solve an absolute problem. And, um, that mattered to me. I think that, you know, my very first sales job, you're gonna laugh, I had to travel with a 1200 baud modem with the wires hanging out of the back of it. And I would just pray that it would connect. I just pray. But I did all my own demos. And, you know, a lot of times now people are so staffed that the sales rep is just the suit. And, you know, there's areas where you can rely on others, and there's areas where quite strategically you should, but you need to know the basics. And I think that that made me better empathize with the business issues, if that makes sense.

Sure. So you, you would do the— just a 2-legged sales call just by yourself?

That's how I started. That's— and I was on the West Coast covering the East Coast. That made it really fun. And that's before they had wheels on suitcases. Oh boy.

So you had to carry the computer and the monitor?

I paid the dues.

Wow.

What'd you like about it, sales?

You know, one of the things that's interesting is I really enjoy the relationships. You know, I think about some of my CIOs that have purchased from me. They've become true friends. You know, everyone goes on their way and evolves with different jobs, but we're still good friends.

Yeah.

And, um, you're solving a business issue, but you also want whatever decision they make to reflect well on them. So I tend to stay after the sale because I want to know that everything I commit to is delivered. And that's how you form long-term relationships. I enjoy that a lot.

And I got to imagine that, you know, was Oracle a matrixed environment back then, or was that before?

Very much so. Very much so.

So how could you go on a sales call by yourself? Wasn't there a school bus involved?

Or—

By the time I was at Oracle, there was a school bus involved, but I had been selling for quite some time before then.

Yeah. And what drove you? Was it the money? Was it the competition? Was it the challenge?

Initially, it was the money. I was in accounting and finance. I decoded how you got compensation.

Oh, so you saw that?

Yeah. So first you had to have engineer in your title, and that worked. And then I went on from there to sales. So, so the money mattered. You know, I was just, I was just starting out, and I was in shock at what it costs to live in Silicon Valley. Yeah, but, um, but I think intellectual curiosity, um, and, and the social nature of it, really, I like it a lot.

Did that surprise you coming from— because I'm sure in finance and accounting you, you thought the salespeople were just suits, right?

I think that there are some that are just suits. I think that you have to differentiate— you have to differentiate yourself, right? And that is one way that Um, by actually bringing value. I mean, when I, when I prep for a sales call, it's— and I build a deck or whatever, it's a cathartic process, and it's not something I do in one sitting. I have to really get inside their head and say, they're going to give me an hour of their time. How am I going to give them value and have them walk away saying that was an hour well spent?

Well, you've got to talk about how it works and all the hours of development that went all the logos, right?

Yeah, the NASCAR slide.

Yeah, I've never heard that one.

Well, it is interesting. I think that you've got to do significant research. And again, that intellectual curiosity, you need to know who you're talking to.

Yeah.

And, and again, just, just make sure that, that at the end of that call, you know what, that was valuable. I want to know more.

Because a lot of people don't even think about what's the value that the client wants. They talk about, oh, we're going to make sure we describe all our differentiators.

Yeah, I think it's definitely been an evolution where I always wanted to start a conversation where I hear about you before we talk about me, because I only exist in relation to you, right? And I see a lot of people that want to tell rather than ask. And that's been an interesting evolution, I think.

And that's how you opened the call? You know, before I get started, can you—

Always.

Yeah.

What was your exact phrasing?

I'd like to tell you it's the same every time, but it's not. Um, you know, we always want to know about your IT landscape, but usually we're starting to talk about the weather or something equally as interesting.

Yeah.

Lately anyway.

And what did the mentors tell you? that really helped you develop your career and saved you a lot of time?

I think about one of the better ones I had, Mike Barron. He was really good at going through, and he always talked about reframing the lens. You know, they're looking at their lens through their day-to-day. You know, they get up every day and they see the exact same thing. I'm disrupting. I need you to take a step back and say, what if? You know, If you never say what if, will you ever truly innovate? Will we ever really get better? And I think that that was very useful for me. 'Cause when you're in a disruptive style of sale, you know, the easiest thing to do is status quo.

Right.

Right? That's easy. And it's, gee, it's gonna be more work. But so what's the value to me? What's it, you know? So he was very useful for me in that area.

And well, let's dig into that because if it is disruptive, how do you prevent That's no decision, no action, or put it on the pile of good ideas for someday?

That's a tough one. That's what we're selling against. I mean, it's— you're really doing risk mitigation on the daily, um, and you've got to again really empathize and, and sit in their seat, wear their hat, and understand where the value is for them. You know, is it more work? Is it Is it just one more thing to do? Could I lose my job? What are the risks? And I've been doing it now for some time, and so I can anticipate what the risks are. And so oftentimes I'll bring it up proactively. Here's some of the concerns I've heard other people bring up. Let's walk through them, and you might have some more to add on. And deal with that elephant in the room, because if it doesn't get asked in front of me, I can't respond to it.

See, a lot of people just hope it never comes up, but it's gonna come up.

I actually created a slide in my deck that actually puts them all out there.

Really? Do you do that on the first call, or does that come later?

I'll do it on the first call because I know that that deck could very likely get circulated, and I want to get in front of the objections, you know, beforehand.

And Who do you typically sell to within the account? Is it CFO? Is it CEO? Is it—

CIO. I'm in the technology space, so CIO is definitely where I would be.

And do you still do 2-legged sales calls, or do you bring a friend?

I often go on my own. When I can bring someone, that's great. I have some outstanding teammates that— and management team that I can bring.

How did you get comfortable learning all that stuff? Because no matter how long you've been doing it, there's a lot of stuff.

There's a lot of stuff, and technology, I think, is particularly bad about that. When I came back to work and I had a lot to learn, my husband's a contractor, and he explained that shower board, which comes at Home Depot in 4x8 sheets, is the same thing as whiteboard. He covered my entire wall with whiteboard. And I would be sitting there and just writing things I need to know, things I need to know, things I need to know, and constantly digesting it. And then I put together a pretty structured self-awareness agenda about, you know, the first of every month I do a 360. Where am I weak? What do I need to foster up? What do I need to get better at? And, um, and I build a plan, uh, and I've actually written this up try to mentor some of the newbies to my company. Because, you know, there's that children's riddle, how do you eat an elephant? One bite at a time, right? So you've really got to have a plan and break it down and stay religious to it. And, and there's, you know, there's, there's always something you don't know enough about. But if you're constantly learning, you're only going to get better.

That's good, because too many people They try and go back to school or they take a class at night, and there's nothing wrong with that. But what you did is like, this is what I don't know and what I need to know.

The other thing that's really cool that I had an opportunity to do was to work with another seller who is, you know, an outstanding seller at my company. And when you take 2 people that are having great success and you put them together, you realize there's not one way to do this. And I'm going to walk away with her ideas and she's going to walk away with my ideas and vice versa. And I would love to see companies do more cross-pollination that way.

Right, because some people it's, you know, 100% relationship, some people it's 100% technology, some people it's top-down, some people it's bottom-up. They all can work.

I walked away with some great knowledge from working with her, so that was great.

And what do you see, or what do you wish you'd done earlier in your career that would have saved you some time? Or given you more success faster?

I think for me, going out and seeking mentors, being very purposeful about what facet of my weaker spots did I want to bolster up on. And I think that's something I've put a lot of time into as I've gotten older.

Yeah. And what do you see as your strongest? point or skill as a seller?

Probably building relationships. I'm kind of, you know, my own personal brand on that, because I do truly care about my clients. They— I care about if they make a decision based on what I've told them, and they've trusted me, I want them to look really good for making that decision.

And what's your approach to that? How do you know when you have it? What are your steps to build it?

Just personal integrity and making sure that you dot every i, cross every t, you're present for every step of the way. Even after the sale, I show up for, you know, some of the calls that I don't need to show up for.

Yeah.

So they know that I personally am going to be there after the sale. Usually at some point in time, I sit down with my CIOs and talk to them about their plans. You know, we We've talked a lot about what's important to the business, and I think we've identified a really solid solution for you. But let's talk about you. Some of my stellar CIOs, Jim Williamson, Bob Leakes, Keith Siegfried, dear friends, we've worked on talking about their personal brand and their goals. Then if they know that I care about that and then we follow through, I've got a friend for life, whether they're my client for life or not.

That is so overlooked.

It matters. The other thing that's interesting is building a community. A lot of the CIOs I work with, they are so busy with their own company, they don't have time to go out and talk to other CIOs. I'd be like, oh, your environment is just like so-and-so's environment. Could I introduce the two of you? Then later on, when I find out that they're good friends and they meet for coffee on the regular, et cetera, and they can rely on each other, I feel really good about creating a network.

What do you think salespeople don't get about CIOs and what they care about?

They're just people. When I sit down with CIOs and, you know, so, what's new? What's on your mind? It's just a conversation. People talking. And if you got a problem that I can solve, that's great, you know. Um, I want them to feel confident that I've been around, I know some people, and I, you know, I want them to come to me first. And I may point them in a different direction than myself, but they know that I will assess the situation with integrity, route them in the most appropriate direction.

Yeah.

So it's just people talking.

And when you cross-pollinated with the other rep, what did you learn?

I am much more seat of my pants. It's instinctual for me. This other, um, my dear friend Donna Walker, she's very structured. And so she and I were laughing that she was learning from me and I was learning from her. And, um, you know, I think I needed more structure. I think there were things that I needed to fine-tune.

It sounded like you were pretty structured. You had your whiteboard, you had your slides.

That was for my own personal knowledge, but the way I presented to my prospects, I could have had more structure. And I've adopted more of her style and made it my own.

So you, what, designed questions, mapped out the flow of the conversation, anticipated pushback or Sticking spots?

Yeah, I think that she just was much more structured as far as mapping out the whole sales cycle.

Okay.

When I was just kind of like taking it as it comes, you know, it's gonna happen, you know, tried to— she much more structured on a mutually agreed-upon plan. And I think that that's something that's a challenge sometimes because sales management and the expectations for all of us is there's going to be a mutually agreed-upon plan. But getting that mutual part is always the hard part. And so there's different ways of saying—

That's always the problem with that. It's like, yeah, we, we, we got it down. Yeah, what did they agree to?

I'm just gonna call it a wish list, right?

Right. Santa, please.

So I just, um, you know, it's interesting. I've learned to introduce it in different ways, you know. Um, I like to have a level set call with the people the person that's going to be my liaison, whether it's procurement or IT director or whatever, and just say, you know, I've done this for a while. These are some of the steps I typically see that are necessary. You might want to add on to this list, and let's just put a timeline that might work for us, and we can change the dates later. But let's just start with that. And I think that oftentimes they're grateful to have someone walk them through things.

That's it. I'm still surprised at how many reps don't realize that these people may not know how to make purchasing decisions.

Right, right. And, and I think that, you know, presenting the objections upfront— yeah, these might be some of the thoughts you're having. If not, let's, let's address any other ones you have. And giving a timeline in the steps that need to occur Are 2 things that can shorten my sales cycle.

Definitely. And I got to imagine that from your accounting experience, you knew the administrative side of procurement.

Yes, I do.

Yeah, see, a lot of people don't know that.

I think that's missed. You're right, you're right. That's a good point, Brian.

I can't tell you the number of engineers who just forward a quote to procurement and say, I need this.

I go, it doesn't work that way.

And that's another art form, right? Um, what is your, um, what is your procurement process? What, you know, what, what, how does that work for you? And I think, you know, sales management will always say, well, who's signing this? Well, you never want to say, well, who's signing this? You've got to come up with your creative way of getting the information you need.

Yes.

And, and it's conversational and it's partnering. There's it, but it's, it's something that I used to struggle with.

And I think when I hear mutual action plan, it's all in the delivery and the style, not the plan.

Right, right, right.

It's getting the other person to—

Here's some typical steps that typically occur. Are there any that need to happen on your side that I'm not aware of?

Right.

You know, I don't want surprises. Yeah.

Well, what's your weakest sales characteristic?

That's probably one of them right there, just nailing down the actual dates and following a program. Like I said, it's going to happen. And so, I've been working on that lately. It's on my list.

Yeah.

The first of every month, I sit down and I think, where am I weak? Where do I need to get stronger in my craft? And sometimes the use of technology is another area. Um, other than my, my, uh, Zoom and Teams skills, um, as we talked about. But, you know, there's so much technology out there that to help you, you know, lead generation using, you know, LinkedIn Sales Navigator and such.

Yeah.

Um, I worked with 2 of the brilliant coworkers that I have that, um, they're younger than I am, and so they, they came up with these tools. I'm kind of learning about them after the fact, but, um, the amazing Frank Zito and Alex Mast, I got on a call with them Just yesterday, and they taught me how to load up my accounts into Sales Navigator so I can tell whether they're hitting our site, etc. And, and that was very useful to me. There's a lot out there.

Yeah. And when you lose a deal, I know it rarely happens. What do you do?

I mean, I think that's the best question you could ask, because that's where you do your learning. You have to do a postmortem. And I do a postmortem on deals that I win, as well as the ones I lose, because no deal is perfect, right? And you've got to ask questions like, how could I have shortened the sales cycle? That's, that's, that's really important. Where were we weak? What, what, what came up that we didn't anticipate? Um, and then you try to bolster those areas, and that comes into my, my 360 that I work on. Yeah, some of it's not just me. Some, some of it's, you know, pretty factual, you know, issues, issues in their organization. But you've got to do a postmortem. I used to actually document them, but I don't do that anymore.

No.

Do you do it by yourself? Do you do it with your team? Do you do it with your manager?

Do you Depends on the size of the deal.

Yeah.

Sometimes just a casual conversation with, you know, your technical team that is alongside you. But it's important.

It's very important. Because I always say, you know, that commission that you lost was the tuition of that lesson.

Well put. Well put.

So you can either learn it or just throw the money away because it will repeat.

You are CEO of your territory. So if you need to see changes that may not be your sales skills, it might be something else you need to. And I think part of the fact that I was a business owner and that I did all the angel investing and wore different hats makes me not shy to speak up and say, Hey, we need this collateral, or, you know, and try to reach out and not just stay in my swim lane. Because what you see on the front lines, your marketing team doesn't see that necessarily. And if you see an opportunity, you have to point it out because it's only going to make you all better.

Well, evaluating a deal is a lot like angel investing because you're like, I'm throwing time and money at this thing. And it's— you either look at it as investing or gambling. Is it a gamble or is it an investment?

Yeah, I play the lottery for profit, for investment purposes too, right?

Well, you know, because I always say like your judgment skills when you look at a deal, because let's say you have a great relationship with the CIO, that doesn't mean they're going to buy. That means they're going to communicate. Does the technology match? Do they value it? Is there some urgency?

You're absolutely right. Yeah.

Yeah.

And again, it goes down to that. If you're disruptive, status quo doesn't— you know, won't get you fired. Yeah. But will you end up on that CEO of the— CIO of the Year list? It's the innovators that try to do everything better that stand out to me. We can do this better.

And when you mentor other reps, what do they typically ask for? What, what's the— what do they really need versus what they ask for?

I guess I think being a good mentor is to not treat them like cookie cutters. It's kind of like being a good manager, you know. Um, how do you like to be managed? You know, what do you need? So I think that giving them some structure to do their own 360s and get better, you know, um, one of the gals I mentored who I think is one of the best reps out there, Brittany Roberts, she, she started— she said she'd be in the middle of a presentation, start laughing because she realized she was using my verbiage. So it was, it was interesting, but she, she, um, you have to be willing to take them all the way through, all the way through From prospecting, creative prospecting, empathizing, wearing the hat of the client, identifying whether you can provide value to them. Then when it comes to accessing internal resources, understanding who's who in the zoo and what you need to bring, and all the way through red lines, I find that oftentimes you don't get that whole beginning to the end. Mentoring people typically only have one area. So a lot of times when I've mentored, um, I start with a pretty solid rep, and then as you kind of listen to them, you just join their calls, listen to them, and it becomes very obvious what they need. And a lot of times it's confidence, and knowledge breeds confidence.

Yeah, a lot, because you can't really be curious if you're not confident.

Right. Intellectual curiosity is everything.

Yeah, you can't ask those hard questions that is going to turn the deal into no decision if you're not confident.

You're absolutely right. And don't be afraid. Again, I think that I have had a lot of peers ask for my objection handling slide because I think it's It's really important to meet it head-on. I'm not afraid of that objection. I have an answer.

Yeah, because is it really an objection or is it the issue? It's just you're gonna face it.

Or a misconception. Yeah, yeah. But I, I think that when I, when I go through that slide, they bring up any others. These— when I do a presentation, it is not just Janet talking, because no one wants that. No one wants to be sold, right?

Right.

Just to— we're just people talking. And so, um, if I get them talking early, then I want— I want— they don't want to hear my voice. I don't want to hear my voice. I want to hear their voice.

Yeah.

And so, um, I, I really want to make sure they're comfortable telling me what they're thinking.

Because I got to imagine that it's not money, it's change. That they're facing more than anything.

Again, I can, I can really drive top line, I can affect bottom line, but the mitigation of the risk, the perception of risk is really the change. You're very much right.

Yeah, great. I really appreciate your time today, Janet. Where can people go to connect and follow you?

Janet Powers on LinkedIn.

The one thing I get out of hearing and talking with great salespeople is that what they tell you is great, but you also have to understand it's how well you do it. It's like that mutual action plan. I remember taking the training on it. And then we went out in the field and my manager wanted to do it. And he, he wrote it up right out of the course and he slid it across the desk to the champion. And our champion looked at it, took a minute, and then slid it right back to him. So it really depends how you do it. I think all of these things are good and helpful. And then I took a very different approach to the mutual action plan. I go, well, I kind of know what has to be done. Why don't I just guide them through it? Because sometimes that mutual action plan can look like so much work that it might discourage things. But like everything that we do with another human being, it's how well we do it. And I think we overlook that particular part of it, and we just focus on how do we know how to do it. Because I think it takes about a few minutes to an hour to learn how to do it. It takes quite a few reps to figure out how best to do it. And depending on reading the other person. I really enjoyed this interview because this person clearly knows how to do the large enterprise sale and has both adapted it to her style and made it effective so that other people can learn from it. This is also up on YouTube if you'd like to watch it in video format without the intro and the outro. And make sure you check out the other shows, Sales Questions, Brutally Honest Answers. Sales Leadership Show and the best of The Brutal Truth. If you want to become great at sales, go to b2brevenue.com, check out the courses. The one we were talking about today is Closing the Complex Sale, where I show you exactly how to do all this stuff, have it be out of your head into writing so you know where you are, where you need to go, what the traps are. And how do you become better at sales? The only way to make more money at sales is to become better at it, smarter, not just working and grinding. That, that's for kids. We'll see you next time.