How do today’s sales leaders navigate the expanding web of decision-makers in enterprise sales? In this episode of ’73 and Sunny,’ we sit down with Stefan Burak, a sales veteran with two decades of experience across a variety of company sizes, from startups to large corporations. Stefan shares his journey from a college classroom influenced by a professor to the forefront of sales innovation, where he navigated through the early days of salesforce automation to today’s necessity of CRM systems. Tune in as Stefan discusses the biggest transformations in sales tools, the critical importance of proving value to customers, and strategies for implementing effective sales methodologies within large organizations.

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Damien: Hello, and welcome to 73 and sunny the podcast about the journey of getting things just right. We talk to tech sales and marketing leaders about how they’re growing, dialing in best practices. And getting closer to that sweet spot today. We’re happy to have Stefan Burak join us. Stefan has been managing sales teams for the past two decades and has worked at some of the largest companies in the world, along with some midsize and startup organizations, giving him a unique perspective on today’s sales and sales challenges.

Welcome, Stephan. Thanks for joining us. 

Stefan: Appreciate it, Damian. Thanks for having me. 

Damien: Glad to have you. Why don’t we just start with how you got your start in sales? Was this a purposeful start? Was this something you fell into? Help us in our audience, understand a little bit about your start in sales.

Great question. 

Stefan: Actually, my start in sales was influenced by a college professor who I took in sales management class, and It was pretty money driven and it convinced me to go down the sales route and it was it was a great push in the right direction. Got into sales that way.

And I, my first software sales job was for a small back then it was called Salesforce automation startup called the goldmine software. 

Damien: I remember goldmine. I remember goldmine and act were the two big. Players in that space back in the late 90s, early 2000s, right? It was our archenemy, definitely.

That, those were, that is to see what has come from those early days of SFA or Salesforce automation to what we have now with basically ubiquitous CRM, which wasn’t even a category before what is the, what’s the biggest change that, that you’ve seen in that space? 

Stefan: You just actually hit the nail on the head.

It was a nice to have not even really on the radar of most organizations to have some type of shared database. In the early days of Salesforce automation, fast forward to today, it’s an absolute requirement. And most organizations cannot really live without some type of customer relationship management system.

It’s, 

Damien: It’s a very interesting dilemma there because a lot of these companies you you have a lot of experience in sales companies in marketing driven companies and at what point, what’s the inflection point? And what do you think? Makes a category go from a nice to have a spreadsheets or Salesforce automation to a need to have.

So CRM. So what do you think is that? Because I think it’s not obviously not just CRM, but it, it is ERP, enterprise resource planning. It is HR systems. It is at what point is it just the maturity of the market? Is it the functionality? Is it the maturity of the market?

The companies that push this is there something in your experience that you’ve seen that makes a category and that could be chat even? We’re seeing chat all over the place on websites or, verse you, we have texting capabilities and different ways of Communicating with customers, but also I know that, you’ve been in a category for the past several years in marketing that is also blossoming as well.

So what is the point at which these companies. Become a need to have 

Stefan: to really that’s a tough, it’s a dilemma based question to be honest because it doesn’t always happen for the software vendors. I think it actually becomes down to the point where you can prove real solid demonstrable value to the customer.

And once you’ve been able to do that on a repetitive, ongoing basis. Then at that point, that category starts becoming more solidified. And in addition, it’s got to have no, it had been noticed by the analyst community and some of the larger organizations. So once larger, we’re going to start adopting a new type of technology, whatever it may be, and they’re showing, proving ROI return on their investment then it starts becoming, more of a need to have versus a nice to have.

Damien: I. I agree with that. And it’s tough that you need these big companies to be able to do that. I know that you’ve sold to very large organizations like Autodesk, ServiceNow, Microsoft, Dell. Like what is, what’s the biggest hurdle that you have found? To sell into that enterprise space because I know that when you and I were actually working together at inside view that was our goal.

It was right. It was like, Hey, first one quarter was like, we need to get, 15 large organizations. Then we need to get 25 large organizations, then 50 and, whatever it might be. What is your experience in, what are the hurdles in getting into some of those very large organizations?

So 

Stefan: I think that there’s a couple of hurdles. So the one getting in is a challenge because you’ve got, not only do you have to get to the, that mid level practitioner that is going to be the user of your technology. But the bigger challenge, and I think that’s the biggest challenge of getting into creating a category is getting the rest of the organization to actually believe there’s true value in whatever the technology is.

So proving value to the practitioner, think about practitioner, what they want to do, they would need to get their job done and whatever their job is, it’s got to be simpler and easier, quicker, faster. Show me how to do it quicker and save me money and make money. That once you get there that’s fantastic.

But then proving it up the food chain, when a lot of large organizations are stuck in their ways is probably the biggest hurdle in terms of actually driving enterprise wide adoption. 

Damien: Yep. And I’ve I’ve implemented nine boxes in the past, right? So where it is, Hey, you need to get in order to get into those.

It’s not, if you think of a like a Brady bunch type of thing, right? Where it is three, three boxes across three in the middle, three on below. And it’s on the columns, it’s maybe sales marketing operations. And then on the Y axis, it is VP manager and then user level. And then if you don’t have that nine box, if you haven’t talked.

To all of those people in an enterprise, you’re not getting that deal done. Nope. Nope. We call it, 

Stefan: Value waterfalls, which is at the C suite. There are certain strategic objectives that the organization wants. That’s going to flow down to the VP level where they’re going to have objectives for their individual groups or departments.

Then the director level and all the way down to the practitioner. So it’s the same idea and you’ve got to prove it all the way up and down. 

Damien: And it becomes as what a lot of organizations have been saying it’s consensus buying, right? I know that we need all this, but we know it is consensus buying in that.

I learned this a while ago, it’s not those people that can say yes to a deal, but it’s the one person who can say no, that you really need to watch out for. 

Stefan: Yeah. And that’s some of the biggest challenges in enterprise selling right now is one that consensus group has probably more than doubled over the past five years from, I think it was seven or eight decision makers up to now 15 or 16, depending on the size of the organization.

Yeah. And in addition a lot of the research has already been done well before any prospective customer talks to a vendor. So if you’re not first in, there’s some research that says that 85 percent of the time, if you’re not first in, you’re not going to get the deal. So you’ve got to be super, super cognizant.

As to whether or not you’re a home potter or not. 

Damien: It’s speed to lead, absolutely. And it’s not just in the B2B side, which I know you have a lot of experience in, but it’s also in the B2C side. So if you’re looking for a plumber, if you’re looking for someone in fencing, like it is, if you have an emergency, the first person to get back to you is like has an over 50 percent chance of winning that deal.

So if you can’t get back to that person in a couple minutes or a couple hours or a couple of days. You’re done. You might, you’re just wasting your time at that point, right? 

Stefan: Yeah. Hence the rise of the conversational intelligence chat. What you guys do that really does give you speed to market advantage.

Yeah. If you do it right. 

Damien: And it’s not only the doing it right is critical as well, but it’s not just about getting to those people as quickly, but it’s getting to them. In the best way. We most people want to be texting as opposed to emailing or phone calling, but it’s also with the right message.

And I know you have a lot of experience in terms of finding that right message. And we use gong internally and we found that if you can’t get to at least you said, sick going from six or seven to 14 or 15 decision makers, we found in gong That if we don’t have at least three people, actually what it was it was the opposite.

If we have three people or more on a recorded call, our win rate goes up above 80 percent just by having three people or more. So it, to your point about the consensus selling, maybe it’s a little bit smaller on our side, but it’s absolutely bearing fruit in terms of, just being able to say this, because decisions aren’t made in a vacuum anymore, especially in a, in an enterprise.

Stefan: Yeah, that’s, and I think that is one of the key things you just pointed out challenges in enterprise selling and mistakes that a, that AEs make a really common one that you just mentioned is you got to be multi threaded because the stuff you just shared with me. Echoes with my previous organization where it was two to three times more likely to close a deal.

If you were a multi bred in a conversation, if you’re relying on one sole champion, you’re probably 

Damien: taking some risk, significant risk. Someone who’s probably saying, yeah, I’m the decision maker. I’m no, the, trust me, I hold the budget. Trust me. No one else needs to say hell. And then until you get to actually the proposal, then they say I’m going to bring in a couple other people.

So yeah, you had mentioned mistakes that salespeople make. What are some of the things that you’ve seen? Salespeople struggle with the most in terms of barriers to being successful. 

Stefan: The one I just mentioned is probably the biggest one. Multi threading is not multi threading enough.

Really latching onto a champion who you think is going to give you the oomph to get you over the line. And in the end sometimes they don’t get there because they really don’t have enough power, authority, et cetera, to do it. So multi threading, super critical. The other one I think is Really making sure that your sales methodology, whatever it is super tight.

I have a pretty strong believer in medic or med pick. And it’s not just going through and saying, are those fields filled out in a CRM system, but actually understanding, do we really have a timeline? Do we really have an economic decision maker that we know what the decision criteria really are and that we’ve validated?

Not just with our champion, but with others in the organization. Because that can lead you, if you don’t do all those things that can lead you down a false app and you’re going to get to a no decision more than likely versus getting the deal closed. So I think that making sure that you really understand, all those critical elements of what and why that decision is being made.

And following through and going deep there. Yeah. 

Damien: And I get that whether it’s a medic or med pick or how many C’s you use. I think I’ve talked to companies that had medic in one with one C medic with two C’s and I believe that I’ve spoken to another company that had medic with three C’s at the end, just for, just to make sure.

But I do think that it is critical to, to have some type of methodology to be able to have. Some type of sales path, right? A roadmap, if you will, to be able to understand, Hey, what am I missing? And I think that a lot of times sales people are doing that just to get the job done, just to be able to close the opportunity or to move it to the next stage.

But I think as leaders of sales teams, it’s a lot different. And for me, it is understanding what are we missing and not having the team waste time with a deal that’s never going to happen. What is the value to you as a as a CRO or a VP of sales that in terms of implementing one of these methodologies, because I think it is different.

Then what it is for a salesperson. So 

Stefan: I think you’re right. I think from a CRO sales leader perspective it is validating the pipeline, validating the deal, seeing if they really do have the right chance of closing. I would also flip it around, whether you’re a CRO or frontline salesman, use it as a tool.

to help your salesperson because the thing you don’t want them to do is spin their wheels and waste time on deals that are never going to close. And the way I would position it or couch it with a salesperson is yeah, I get it. It feels like you’re filling out all these fields just to satisfy some reporting requirement.

That is not the case. The reality is they are there To help you win the deal or disqualify it, close it, lose it. And it’s not just satisfying, the C level folks on the reporting side, it’s figuring out what deals do you really have a viable chance of winning? And what should you actually walk away from quickly?

Hard on the sales person to do that because they always want to have a lot of deals in the pipeline. But I’d much rather have a smaller amount of deals and a high win rate than spending a bunch of time on deals that I didn’t have a chance to win in the first 

Damien: place. Predictability. That’s what we want.

And I was asked the other day, what keeps you up at night? And I said, I don’t know, meaning that it’s the things that I don’t know. That gave me up a night. And that’s, it’s the predictability. Again I’m, I would much rather say, Hey, listen, I’d rather have less things in the pipeline, knowing exactly where they are and knowing that they’re going to close then having half of it be, I don’t know, because I don’t want to be surprised from Bertram.

Maledi would always say the CEO and founder of InsideView and now the head of engineering for demand base would always say I don’t like surprises and whether they’re good surprises or bad surprises, if they’re bad surprises, that’s the worst. But even if they’re good surprises Hey, we got this deal that mean that means that you didn’t have, or the sales person didn’t have a good hold of that deal.

They didn’t understand everything. They didn’t. Check off all the boxes. So then they’re surprised when it did. I think there are some times where a surprise might happen, but if it happens all the time, that means that just someone isn’t prepared. 

Stefan: They’re not digging deep in the deal.

And that’s why deep dive deal reviews feel like an extra work from an AE’s perspective. But in fact I believe they are actually going to be very helpful to the AE to, again, go back to the idea of. Let’s focus on what you can win. Let’s move this stuff that isn’t really real out as quickly as possible.

And that should help you get get your quota. So I totally agree 

Damien: with that. What is, what’s your, do you have any tips or tricks in terms of getting sales people to adopt something like that? Because I look at it and lovingly say. It’s like getting kids to eat their vegetables, meaning that no one wants to eat the vegetable.

They just want to go for the, the, chicken nuggets or the mac and cheese or whatever it might be. To get salespeople to do something, just like getting kids to eat their vegetables they need to feel like they’re part of the process and they’re part of the decision making process as well.

If you go to the store with young kids and you say, Hey, what? What do you want to eat for dinnertime? Do you want broccoli? Do you want cauliflower? Ooh, this is really, bright or colorful. And then they can pick it out, and then you bring them into the kitchen, and you help them season it and cook it, and, do everything, and then once you put that on their plate, They are so much more likely to be eating those vegetables as opposed to if you just put it on their plate and say, eat this, right?

So that, that is my thing is that I like to go ahead of it and say, what do you guys think? What do we need from a perspective from a I wish I had that strategy when my kids were really little, 

Stefan: cause I didn’t 

Damien: do 

Stefan: that 

Damien: enough, 

Stefan: but I think you’re actually spot on right there, which is. Yeah. A really good sales process should also have sales team involvement.

So if you involve the team in the structuring of the process and getting feedback from them versus handing it down from on high and saying, you’ve got to follow this, I think you’re going to get a a much higher result. And the other thing that I think is important is to use examples of really successful salespeople that are following the process and showing the difference.

So salesperson a, their pipeline is X, but they’re, and it’s not as much as yours, but they’re closing 50 percent of it and they’re reaching their number. You’re only at 25%. If you adopt some of these practices, what do you think can change? So involving them in the process and showing them. What the results could be at the end and then working through it all the way is I think the way to do it versus just dictating what they should do.

Damien: I think that you’re right. That is a great idea. And bringing that person on early, identifying who’s the best seller and then bringing that person on your sales change management council, to be able to say, Hey, listen, here’s what we’re thinking. Can we use your stats? If you start using this and then be that, flagship for the rest of the team.

But I think that’s a great idea. And it also comes back to similar to what you were talking about with the. Enterprise selling into enterprise. It’s the value. What is the value to the sales team? It’s not just, as you said, putting it on a spreadsheet and just if you’re trying to sell into an enterprise organization, they need to understand, Hey, the value that you’re going to be bringing to them as either as an organization or as a selling team and what effect this will have.

And then to your last point about getting someone who’s really good, what measurement are you going to be using? Hey, listen, they, this person in this MedPIC methodology, they got 50 percent more calls. They got 50 percent more callbacks. They got 30 percent higher win rates, whatever it might be to be able to say, here’s the value and here’s what you could get.

If you just put it, put to that, it’s not a VP of sales mandating this. It’s the data. It’s Hey, here’s the data. If you want the date, if you want this then you got to go for it, right? Totally agree. So we’ve been talking a lot about. The sales side I’d love to get, you, you’ve been selling to marketing CMOs VPs of marketing directors of marketing for many years.

We’ve just been talking about a lot of the sales trends. What are you seeing in terms of some of the marketing trends today and how. How that’s changed, 

Stefan: It’s changed a lot. There’s a number of things that are really influencing that. So one digital transformation is happening.

It’s happened for sure. In a lot of the smaller organizations that have adopted easier, adopt some of the newer best practices, but it’s definitely happening in the enterprise too. There it’s a longer much more significant change and change management that needs to happen. But we’re seeing that the move to online is absolutely real.

It’s happened. It’s really started in COVID or even before that, when it really got accentuated during COVID. And now it’s there. So digital tools are really a key thing. The other piece that we, that I see is account based marketing. You came out of demand based, I came out of follows.

That is a real thing. The idea of just MQLs and then throwing, getting a bunch of MQLs and then throwing them over to a BDR team to qualify, to go over to sales. It’s just, it’s too hard and it’s too expensive now. So being really precise. And going after your ICP and leveraging account based marketing strategies is definitely taken hold.

And the other piece, of course is data data driven decision making, and then the influence of AI. Which, I think, in the enterprise what I’ve seen is, A lot of interest, but a lot of what’s the right word? Maybe a slight, not skepticism, but nervousness of what it can and can’t do and what it could possibly mean from a compliance standpoint.

Damien: I think that those are all really good points in terms of the ABM in terms of the data, which I think has always been important, but the AI side as well, and I think it is. People want to be, have the authenticity of a human, but have the efficiency of AI, right? And to marry those two together, and I’ve said it on a 73 and Sunny in the past, but to be able to marry those two things is a really hard It’s a really hard task to be able to get the machine cranking all the time.

A hundred percent feedback, being able to speak in a conversational format is a pretty difficult thing to do. Are there. Are there things in AI that you have implemented in the past? 

Stefan: Sure. We’ve used a number of AI tools from to, for help generating emails to doing research on companies.

From a, just this is for more of a sales side. And I think you’re absolutely right. Is you can get pretty close to being authentic, but you’re not always a hundred percent there. So getting the AI and just expecting it to be a hundred percent authentic is not necessarily a given right now. So I think that going the extra step and not necessarily making sure that email is going to go out the door because we believe it was written by AI.

Just checking in a little bit and doing some checks and balances, I think is what my experience has showed me. 

Damien: And yeah, it’s a good point. And I do think that the authenticity of AI is going to lead people to rely on more Of what they do know to be true, which are people, which is networking, which is, having that check and balance.

And so I know that you’re in pavilion. Tell us a little more about pavilion your experience there and maybe your thoughts on the importance of networking. 

Stefan: I think the ports networking is absolutely critical. Think about being on a job on it right now. You’re going to, you submit a resume on LinkedIn and it’s easy apply or whatever they say, you’re one of hundreds that are being looked at and it’s getting screened by AI and unless you’re a professional.

You get every single keyword, probably not going to get that callback for the interview. So networking and being connected and being out there is absolutely critical because and that’s just not on job search that’s on. On selling as well. Organizations like pavilion, which is professional networking organization, focused on, on SAS, I think is a great way to connect with peers and colleagues to get different viewpoints and perspectives on things just like we’re doing right here.

So that type of organization, and then there’s SaaStr, there’s a bunch of others. That I think are really helpful and Delama I’d recommend being part of all of them. 

Damien: Awesome. 

Stephan, thanks so much for your time and insight here. Again our guest today was Stephan Burek, a very seasoned experienced VP of sales.

If you’d like to connect with Stephan you can find him on LinkedIn or Pavilion, or probably just walking around the Marin headlands maybe. But Stephan, thanks so much for your time. I appreciate it.

Stefan: Thanks, Damien. I appreciate it as well.