Digital-First Leadership

Ep. 22- Winning the Six-Figure Sale with Jeff Goldstein, Part 1 of 2

May 17, 2022 Richard Bliss Episode 22
Ep. 22- Winning the Six-Figure Sale with Jeff Goldstein, Part 1 of 2
Digital-First Leadership
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Digital-First Leadership
Ep. 22- Winning the Six-Figure Sale with Jeff Goldstein, Part 1 of 2
May 17, 2022 Episode 22
Richard Bliss

In this episode, Richard is joined by Jeff Goldstein, former head of sales in major tech companies turned solopreneur. They discuss what a complex sales campaign is and the first 3 out of 10 steps needed to win more big deals.

Host: Richard Bliss
Guest: Jeff Goldstein
Podcast Manager: Kimberly Smith

Follow Richard Bliss on LinkedIn:
Find Jeff Goldstein on LinkedIn:

Show Notes Transcript

In this episode, Richard is joined by Jeff Goldstein, former head of sales in major tech companies turned solopreneur. They discuss what a complex sales campaign is and the first 3 out of 10 steps needed to win more big deals.

Host: Richard Bliss
Guest: Jeff Goldstein
Podcast Manager: Kimberly Smith

Follow Richard Bliss on LinkedIn:
Find Jeff Goldstein on LinkedIn:

Speaker 1: Welcome to Digital-First Leadership, the podcast that focuses on helping leaders and teams understand how to master the language of social media in today's digital-first world. 

Richard Bliss: Jeff, thank you so much for joining me. It's great to have you on the show. Jeff Goldstein: Thanks, Richard. Great to be here. Thank you. 

Richard Bliss: Now, Jeff, if I were to meet somebody in a restaurant or in a networking event and I was to introduce you, how would you want me to introduce you? What it  is that you do and kind of the value that you bring to the customers you work  


Jeff Goldstein: Sure. Well, what I would say Richard is I spent the last 25 years leading the  Canadian subsidiaries of some pretty large tech companies in Canada. So I had responsibility for the subsidiaries, and after 25 years of doing it, I said to myself,  maybe it's time to give up the weekly forecasting business and retire. So that's what I did. 

Richard Bliss: When you talk about that weekly forecasting, we're obviously not talking about the weather. 

Jeff Goldstein: No. So when I talk to other sales leaders and I talk about "So how often do you  forecast?", it's "We forecast every week." When I ran NetApp Canada and  

Veeam Software in Canada, every single week, we rolled up a forecast call. And as the sales leader for the country, I would have one forecast call with my team and one forecast with my boss. So if you do the math, I've done about 3,000 forecast calls over my career. And so I say, I've given up the weekly forecasting business called sales leadership. Anybody in sales leadership in technology  

certainly smiles and says, "I totally get what you're saying." 

Richard Bliss: So you stepped away from that. And what have you stepped into then? 

Jeff Goldstein: Yeah. So I'm too young to do nothing, and I'm up here in Canada, up north. You can only golf half time of the year. So I've built a solo sales consultancy I call  

Winning the Six-Figure Sale, and what I do is I help sales leaders in technology  

win more big deals with a proven three-step system that I really developed  

while running NetApp and Veeam Software. So I help sales leaders win big deals and help them run complex sales campaigns. That's what I do now. 

Richard Bliss: So help me understand then what would be some of the challenges that these sales leaders are facing when they're trying to do a complex sales deal? And I  

guess we'll start with, first of all, what's the definition of a complex sale? 

Jeff Goldstein: Right. So I call it Winning the Six-Figure Sale because six and seven-figure sales campaigns, unless they're back into an existing customer where you're just  

upgrading current technology, they're usually, if they're competitive, they're 

complex sales campaigns. There's many steps that a sales team would have to  

go through. There's many stakeholders that they would have to meet. And  

that's a lot of things to keep track of to run a good sales campaign. So that's  

what I mean, midsize to large enterprises, complex sales campaigns, lots of  

steps, lots of stakeholders. It takes a very intentional and deliberate process to  actually go through, if you're not going to miss something that could sink your  


Richard Bliss: So what I'm hearing then is that you've got this euphemistic forecasting job that  you had, and now you stepped in and said, okay, I'm guessing is here's how to  

be more accurate with that forecasting. Go ahead. 

Jeff Goldstein: Yeah. So the net result of running a sales campaign, a good sales campaign is  you win more big deals, and winning more big deals has a dramatic impact on  

your sales forecast. So I tell people, my program is not really about forecasting,  but if you run better sales campaigns, these are usually the big deals that move  the forecast needle. These are the deals most sales leaders depend on to  

overachieve their sales targets and their forecast. So I don't really teach people  how to forecast. I teach them how to win big deals, which, in the end, helps  

them more accurately forecast when their deals are actually going to land. 

Richard Bliss: Oh, got it. And that certainly helps me understand a little bit better, because I  think as we've talked about it before in other conversations, you've identified  

really, what is it, 10 steps into that sales process, right? 

Jeff Goldstein: Right. 

Richard Bliss: So I think 

Jeff Goldstein: Absolutely. 

Richard Bliss: ... rather than cover all 10, let's cover five of them. What would be the first, let's  talk about that, the first five steps that you think are important to moving you  

towards that, winning that six-figure deal? 

Jeff Goldstein: Yeah. So I really break the process into two, and the first one is really got three  steps to it, and then we go from step four to step 10. So we'll talk about the first  three, and the first step is really if it's big and it's complex and you're part of a  

fairly large organization, you're going to have to get your deal approved because  typically, big deals mean big discounts or low gross margin. So often, large  

organizations have a deal desk or they often require that approval is needed  

beyond the first-line sales manager. So I tell people, what are some of the things  you want to think about when you're trying to get your deal approved? And  

first, you describe the deal. How big is it? How much future revenue is there, if  we win the deal? As a VP for the country, I was always more interested in deals  that had future annuity revenue to them. Right?

So we like big one-shot deals, but I really preferred when we landed a deal and  then there was a lot of future annuity to the deal. So one of the questions I  

would ask is, so if you win the deal, is there follow on business? Yes, there is.  

What's the get-well plan? What do you mean? Well, we're going to have to get  really aggressive to win the deal, but once we won the deal, how do we improve  our position over time, so we don't have to sell at these goofy prices forever  

inside this account? And that simple question really requires sales reps think  

about the art of their deal. How do they architect their deal, so the customer  

feels like they're getting a really good deal up front? They're very competitive  

on price, but then the sales rep can get away with selling at lower discounts  

over time to make up some of the margin that they lost. So those are some of  

the questions just around getting your deal approved. 

Richard Bliss: And then the 

Jeff Goldstein: Here's another 

Richard Bliss: And so 

Jeff Goldstein: Sorry, go ahead. 

Richard Bliss: So if a salesperson doesn't know who's going to approve that deal, are there  certain ways that they find out sometimes? Is it just flat out asking who do I  

need to talk to? 

Jeff Goldstein: Well, so far, this is just inside their own company. So before I can get... Yeah. 

Richard Bliss: You're talking about actually in the man. So I'm a sales rep working for this tech  company. I want to make this deal. I need to get it approved internally in my  

own company that I'm allowed to do the discounting. I'm allowed to price it at  

this point. That's what you're talking about. 

Jeff Goldstein: That's right, because often, big deals will require discounts bigger than sales  reps are authorized to give. 

Richard Bliss: Got it. 

Jeff Goldstein: So they've got to go to their manager, and he will often have to go to his  manager if they want to get really aggressive. And so I'm busy reviewing an  

internal deal and I go, okay, what's the discounts? What's the margin? How  

much future business is there? What's the get-well plan? And before we even  

started, the rep goes, "Well, I never really thought about how I'm going to  

reduce my discounts over time." Well, depends how you architect your deal.  

Then I ask him, have you got any special terms and conditions we might not  

enjoy? "What do you mean?" Well, if you sell to a large account, often they  

want limited liability or indemnity or most favored nations pricing.

So there are some terms and conditions that large banks, telcos, government  

agencies will require from their vendors that give their vendors heartburn. So I  go very early on, do you know if there's any special terms? If you're responding  to an RFP, what are those terms we need to pay attention to, so we can get our  legal folks involved before the deal's about to close? So those are all the very  

first questions I would ask in the review that often reps go, "Why are you asking  me all this? I have no idea." Well, we should be thinking about this stuff as we  

architect our deal. 

Richard Bliss: And that's really just step one, right? 

Jeff Goldstein: That's just step one. We've barely got started. And then step two and three is all  around, is the deal qualified? Right? And I go... And I didn't invent this. This is  

called BANT. IBM invented this a thousand years ago. Budget, authority, need or  business outcome, and timing. Those are four elements of a deal you want to  

understand from the customer's perspective, so you know if you should spend  

time on the deal. Is it well qualified? Things like, has the budget been approved?  Has the budget been released? 

For the last two years, we've been in COVID. So the question is, what's changed  in the customer's budget approval process? And I ask reps that now, and they  

go, "Well, nothing." Well, I go, that can't be. VP of finance have a lot less  

revenue coming in these days for most organizations, not all. So a lot has  

changed in the budget approval process, given COVID, and reps need to go off  

and really think about what that looks like, and they need to go explore that  

with their customer. 

Richard Bliss: So B is the budget. And then A? 

Jeff Goldstein: Is authority. Are you speaking to the people who have final authority to say yes  on your deal? Or are you talking to somebody who can just say no? And there's  a big difference, right? 

Richard Bliss: Right. 

Jeff Goldstein: And I build this little thing in my program called a relationship map, and the  relationship map really just talks about who are the key decision makers that  

are going to impact your deal. And then I ask them three questions. Have you  

met them in person or on Zoom? Is the person pro, neutral or against you? And  then what are they in the decision process? Are they a decision maker, a direct  influence or an indirect influence, or a coach, a fox? And we really map this out  on a little, I called it a relationship map, way easier to understand than a  

complex org chart, which doesn't always really tell you who's in the power base.  So 

Richard Bliss: And something that we do when we work with our sales people is we use Sales  Navigator. And I tell them, look, you're going into a company that's got 10,000 employees, right? So oftentimes, they want to start with the decision maker.  

And I tell them no. Use Sales Navigator, do a search through all 10,000  

employees for prior work at your competitor. Have any of these employees ever  worked for your competitor? Because that's going to be, as you said, those  

hidden landmines of people who might just get in the way that you have no  

idea, because they don't show up on the org chart. Right? And it's also a way to  find allies. Has anybody ever worked at your company before or a previous  

successful job that you've had? And Sales Navigator is a great way to do that. So  I like that, what you're talking about, that relationship map. Find out what those  relationships are in there. I like that. 

Jeff Goldstein: I think I'm going to add that to my list, Richard. That's a great question. Richard Bliss: Right? 

Jeff Goldstein: Because those are usually the people who aren't supporting you. They have  prior bias. And we know, as you navigate through a large sales campaign, there  will be people who like you, people who are neutral and people who are again  

you, and often they're again you because they work for your competitor, and  

they still have close eyes to that competitor. Makes great sense. 

Richard Bliss: So we've got B, A. 

Jeff Goldstein: Right. And the last thing I do with the relationship map is if you've met them in  person and they're pro your solution, a little box on the map turns green. 

Richard Bliss: Okay. 

Jeff Goldstein: If it doesn't, it's red. And I can very quickly look at a relationship map and see  how wide and deep a sales team is selling. I work for tech companies. Often,  

tech reps like to sell to technical people with money. So they're comfortable  

talking tech feeds and speeds to other technology people, but they aren't  

comfortable talking about money or business outcomes. And so typically the  

financial decision maker is red, right? Often, the line of business, the person  

whose business is going to be enabled by this solution is red. 

And so I can quickly look at a relationship map and go, you're only selling to the  technical buyers, but we know in complex sales campaigns, there are often five  to six key decision makers and they're not all technical buyers. And so the  

authority piece is one to understand how wide and deep we're selling. Do we  

have access to power? Are we talking to the people who can say yes? Or are we  just talking feeds and speeds to people who like technology and are like us,  

right? So we're kind of step two into this thing, and then we've already  

discovered some things that people didn't know before. Right?

Richard Bliss: Yeah. And so then the third BANT is now need, or as you say, business  outcomes, right? That is, basically to distill, are we really solving a problem  

here? Or what is the problem that we're solving? 

Jeff Goldstein: Right. And so it's really interesting. For tech people, they often talk about  technical needs. I need faster disk. I need faster servers. I need my network to  

be faster. One of the questions I ask is what business outcomes is the customer  expecting from your solution? Wait, business outcomes? Because customers  

have lots of problems. They typically only solve problems that have a real  

impact on their business. And so I go, what are the business impacts? What are  the business outcomes you're trying to address? And can you articulate those  

into financial terms? 

Now, I've really often got sales reps out of their comfort zone because they can  talk about feeds and speeds till the cows come home, but what business  

outcomes and what financial impact will your solution bring to the customer  

from their perspective. And if the rep can answer that, we start to get a sense  

for, okay, this problem I'm solving has a big impact for customers and that's  

going to motivate them to close. 

So as an example, think about the last two years. At the beginning of the  

recession, sorry, at the beginning of COVID, nobody was talking that much about  work from home, but all of a sudden, COVID hit and customers had to spend  

money to enable their employees to work from home. Often, those projects  

weren't in the budget. They got reallocated from other budgets. What was the  

business outcome? Well, strategically relevant, tactically urgent, provide rapid  

time to value, some of the other qualification questions. And if a project was  

those three things - strategically relevant, tactically urgent, provide rapid time  

to value - it would get approved. Think about all the work from home stuff was  just that. So if you were working on a three-year business process engineering  

project when COVID hit, the money allocated to your project might get  

reallocated to just get employees to work from home. And all of a sudden 

Richard Bliss: Go ahead. 

Jeff Goldstein: All of a sudden, different projects were getting approved because the business  need had changed. And if the rep was just thinking about [inaudible 00:15:50]  

and speeds, they would've missed that completely. 

Richard Bliss: Yeah. We saw that heavily because what we do, obviously, at BlissPoint is  helping sales reps understand how to build the relationship and begin  

negotiating and closing deals online, in a digital environment, particularly  

through LinkedIn, and where before, that was a nice to have. When COVID hit,  

that became an essential, that if you no longer had the ability to get on a plane  and go shake the hand and meet and talk to your prospect eye to eye and face  

to face, suddenly, how do you do that? And so many were unprepared for that,  and that's why we saw that business outcome was, how do I help my sales reps get in front of prospects and customers where they have no ability to do that  

through physical activity. And that, we saw that exactly what happened. And a  

lot of budget got shifted over from events and activities and travel. It's like,  

okay, we got this money. Let's teach them how to actually do that online. 

Jeff Goldstein: Totally. I was chatting with a VP of one of the large mainline distributors in  Canada. Right? He runs a very big business, and it was probably June of 2020. So  we were just kind of in the beginning steps of all this COVID stuff, and I said,  

"How's business?" fully expecting him... 

Speaker 4: Jenny. 

Jeff Goldstein: Sorry, guys. 

Richard Bliss: That's all right. Happens to all of us now, right? 

Jeff Goldstein: Work from home. What do you know? So I was asking him how business, fully  expecting him to lament a little bit about how business was down. And he said,  "Hey, Jeff. If I had 15,000 more laptops this quarter, I would've sold them all." 

Richard Bliss: Yeah. 

Jeff Goldstein: Right? And those 15,000 laptops weren't in the budget early on, but all these  projects were strategically relevant, tactically urgent, provide rapid time to  

value. Then people needed to get trained to work on Zoom, work from home,  

build relationships, all the stuff that you do that completely changed. So that's a  big, that's a whole thing around qualification, around not just technical need,  

but business outcomes. And I find sales reps can truly differentiate themselves,  if they get educated and get comfortable talking about business needs as well as  technical... Sorry, business outcomes versus technical needs. Big lesson for sales  people. 

Richard Bliss: It is. It's a big shift, particularly in this tech that you and I have both spent our  entire careers in, getting away from talking about the technical. And that really  is the new role of the salesperson today because as we know, our prospects  

clients, they have gone out, done the research. They've been online. They know  the price. They know the features. They know everything they need. Now, they  just need you to talk to them to see if you understand their business. Right? And  so that's a critical component. 

Jeff Goldstein: That is a very significant change and why some sales people really won't make it  in this whole new world. 

Richard Bliss: Yeah.

Jeff Goldstein: There's going to be a lot of sales reps who find that what was a tough business  before becomes even more difficult because the expectation of sales people  

goes far beyond just the understanding of their technical specs. 

Richard Bliss: Absolutely. So we only have a couple of minutes left. Let's wrap up with the...  Because we got the B, budget, authority, need, and then the T. 

Jeff Goldstein: Timing. So here's another great question I ask. So what's the compelling event  that's going to make this deal close as expected? And I get all sorts of answered  from, "Hey, the quote expires on Friday." And I go, just a minute, buyers today  expect the price you gave them on Friday is the price they're going to pay on  

Monday, whether it's your quarter end or not. So put limited time offer pricing  aside, because especially in complex sales, that doesn't work. 

Then they go, "The maintenance contract's expired." Well, if you're the  

incumbent vendor, you can play all sorts of games with when maintenance  

expires, and no vendor I know tells customers when the maintenance  

agreement has expired that they're not going to get support on Monday if it  

expired on Friday. So that's not a good one. 

So the last question I ask is, what's the compelling event? And then they get all  these flowery answers, and then I say, "What happens to the customer if they  missed a compelling event?" So just think about that. What happens from the  

customer's perspective, if they missed a compelling event? And if nothing  

happens, it wasn't that compelling from the customer's perspective. 

Richard Bliss: Right. 

Jeff Goldstein: And reps, their shoulders go down and they go, "Jeff, that's not fair." Well, not  every deal has a compelling event, but thinking that you have a compelling  

event when you don't is even worse, because then you get this false sense of  

security that your deal's going to close when expected, because something  

magical is going to happen to the customer on Friday, the last Friday of the  

quarter, that doesn't happen. So those are the first questions. 

Richard Bliss: I like that. I like that because in our case, one of the compelling events we often  see is they've made an investment. For example, in Sales Navigator, a very  

substantial investment and they're not getting their money out of it, and now,  the renewal's coming up and we have to decide if we're going to keep this  

product. So there's two compelling events here: one, the person who made the  commitment to invest it, and two, oftentimes, the LinkedIn Sales Navigator rep  who really wants... So there's two compelling events here, and this is when we  get pulled in. Can you help us justify and validate that we are getting value out  of this? And so when we step in and start training salespeople, we understand  we're there to teach them to rapidly adopt and find the value of this before the  renewal comes up, because some of those Sales Navigator deals are million  

dollars plus.

Jeff Goldstein: Totally. And that's a great example. I tell reps, if the customer's building out a  data center and you're selling storage and they've already bought the  

networking equipment and they've already bought the servers and they've  

already bought VMware and got it all installed and you're the last element and  you're approaching their go live date, that's pretty compelling. Customers  

typically will do that. But if you're one of three vendors going into the data  

center they haven't bought anything yet, and you're saying, oh, they got to be  

up and live on September 1st and it's August 15th, pretty likely, your deal's  

going to slip. So just knowing if there's a compelling event and taking the happy  years off in the process is what we explore in this section of the review. 

Richard Bliss: Oh, this is excellent. Jeff, thank you so much for spending the time. There's a lot  more here to cover and unpack from the book and from your step process. If  

you're okay, we're going to go ahead and have you back and come back and talk  about these elements in another episode. 

Jeff Goldstein: Fantastic. I look forward to it, Richard. Take care. 

Richard Bliss: [inaudible 00:22:29] great. And if people wanted to find you, how do they track  you down? 

Jeff Goldstein: Pretty simple. is my website. You'll find some videos there  about the program. You'll also be able to reach me at I'm pretty easy to reach. I'm active on LinkedIn. You  can reach me there as well. 

Richard Bliss: Yeah. We're big on LinkedIn here. So that's great. Jeff, thanks again. Thanks for  being here. 

Jeff Goldstein: All right, Richard. You be well. Take care. 

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