Burn The Playbook - B2B GTM Strategies with Marc Crosby

Stop Pitching. Start Investigating: The WINGS Playbook with Raz Vicerabin

• Digital Rebels Consulting - Marc Crosby

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0:00 | 42:44

B2B sales for founders: how to run real discovery, align a proof of value, and close without racing to discounts. Outcome: shorter cycles, cleaner handoffs, and deals that stick.

In this episode of the Burn The Playbook Podcast, host Marc Crosby (Digital Rebels Consulting) digs into the WINGS Sales Program with Raz Vicerabin. Raz led revenue teams through IPO at Riskified and now teaches founders the sales fundamentals. We cover mindset shifts, first hires, metrics that matter, and a dead-simple POV alignment that stops deals from dying after the demo. Raz is bringing WINGS to NYC on February 3–4, 2026. (LinkedIn)

What you’ll learn

  • Why discovery beats pitching and how to stay in investigator mode
  • A 15-minute prep routine that saves wasted meetings
  • The POV Alignment: success criteria, effort, economics, green light
  • Negotiation basics founders miss and how to anchor high with a pricing ladder
  • When to hire your first AE or VP Sales and what must be true
  • The two pipeline “cemeteries” and how to build momentum after a demo
  • Metrics that matter: stage-to-stage conversion over “big pipeline” vanity

Chapters
00:00 Intro + who is Raz
00:38 Recording at Riverside
01:48 Raz’s path: law, IDF interrogator, first AE
03:21 Builder-to-investigator mindset shift
04:53 The #1 mistake on first calls
06:28 How to prep for discovery
09:22 Teaching sales at universities vs founders
11:34 The WINGS program format
12:14 1:1 consulting vs workshops
13:32 Negotiation influences and ZOPA
15:36 Handling aggressive buyers
17:00 Discount pressure and value gaps
18:25 When to walk from a deal
19:43 Timing the first sales hire
21:05 Bad metrics vs stage conversion
22:25 Why deals get “stuck”
23:13 The POV Alignment framework
27:55 Curiosity as the top trait
29:24 Burn It or Build It: 10 hot takes
41:14 Where to find Raz + NYC dates

Who this helps

  • Early-stage founders in B2B or cyber selling into the enterprise
  • Technical leaders new to sales who need a practical operating cadence
  • Sales leads cleaning up post-demo drift and endless POVs

Guest

Host

Views expressed are our own and do not represent any organizations

© 2025 Digital Rebels Consulting. All rights reserved.


Digital Rebels Consulting (00:00)
Welcome in. I'm Marc Crosby. This is burn the playbook. My guest today is Raz Vicerabin who is an experienced B2B sales leader who has built sales teams from zero to scaling and led revenue organization through successful wall street IPOs. Today he teaches B2B sales at universities and entrepreneurship programs and works closely with early stage founders on building their sales motion. Ross is also the creator of wings, his sales program for founders, where he helps founders learn the B2B sales fundamentals. Welcome Ross.

Raz Vicerabin (00:30)
Hello Marc pleasure to be here. Thank you.

Digital Rebels Consulting (00:33)
So where are you calling them from today? think you have an interesting background there.

Raz Vicerabin (00:38)
And I guess that you don't mean only Tel Aviv, right?

Digital Rebels Consulting (00:40)
not just Tel Aviv, but you're in a very special office.

Raz Vicerabin (00:44)
Exactly.

So I'm actually calling from the Riverside office, which is also the software that we are using in order to record these podcasts. And this is ⁓ an incredible company that one of the founders is a very good friend that we share some experience selling together in the past at Riskified.

Digital Rebels Consulting (01:04)
Very cool. Awesome. Love that. ⁓ so looking at your business, for wings, I'm pulling some copy directly from your website that says founders are some of the smartest and most talented individuals, yet many come from a technological background with little to no sales experience, which I think is fantastic because I think that you lead, you know, founder led companies, SAS and tech. typically have those same exact discussions and the manufacturing.

side of it, far as just engineers and chemists coming from, you know, very technical backgrounds and learning sales because sales is not taught in universities. ⁓ but tell me a little bit more as far as how you got into sales. also know from your background, you do have a law degree, so you're very well accomplished, but how did you get into sales and then how did you start your business wings?

Raz Vicerabin (01:48)
So I think I'll try to keep this short because I think it's interesting and a little bit messy, but I'm a son of a teacher and a son of a salesperson. So I think that what I kind of do today is the combination of my parents' traits. And I think that my first sales position was actually in the Israeli military. I was a criminal interrogator. And in the way that I view it, one of the main things that is selling is persuasion.

And I think that when you think about it, it's ⁓ probably easier to sell someone's software for a few hundreds of thousands of dollars than confessing and going to jail for a few years. So I think that this was kind of my first sales profession. And I thought about positive things about sales all my life, because that's where I was brought up with my father and traveled with him to his customers, at least when he worked in Israel. And later on, I actually went

to study law, went to law school. I hated it, but I decided to do the internship and take the bar exam, and then I decided to leave the profession because I understood it's not for me. And especially when you live in Tel Aviv and when you live in Israel, where you wanna be probably is in the tech scene. And I saw an interesting opportunity to be a first AE for a startup in the IOT space back in like 2015, where IOT was like a very big thing.

and I jumped on it and I was lucky enough to be offered the opportunity and think the rest is history.

Digital Rebels Consulting (03:21)
Nice. Very cool. ⁓ so you teach founders, ⁓ selling today. what's typically like the most common, mindset shift that, that you typically deal with, what do they struggle with as far as just building the product to learning how to sell.

Raz Vicerabin (03:35)
So when I think that founders in general are builders, they are focused on building the product, many times they also believe that the product is like the greatest thing and probably the best thing after the invention of fire. And I think the big shift in mindset that in my opinion they need to do is to go and become much more of an investigators, actually going back to my military service.

much more curious, much more investigating, asking questions, understanding the pain, conducting discovery, than actually focusing on their product and selling their product. And I think that that's the main mindset shift. Be much more listeners than talkers and sellers and persuaders.

Digital Rebels Consulting (04:22)
Absolutely. Yeah. Yeah. think you have to have a more of a detective mindset. I've always kind of, guess, appreciated ⁓ law and investigating the FBI and those kinds of shows and movies and things like that, because I think that's the sort of mentality that you need to have if you want to be effective in sales. ⁓ When you typically walk people through as far as just making a discovery call and just making a sales call, ⁓ what do you find that? ⁓

people make the most mistakes doing when they're going through that initial process.

Raz Vicerabin (04:53)
So I think that probably the main thing is pitching before conducting actual discovery. And it's interesting because yesterday with one of the startups that I work with, I took a simulation call with like an AE that has seven years of experience. And we did a sales call simulation, intro call, discovery call. The first thing that he was doing is pitching. He left 10 minutes at the end in order to actually give seven minutes of the pitch and ran out of time in order to schedule the next steps.

So I think this is one, I was very surprised that someone with like seven years of experience conducted an intro call in this format. But I think that founders, especially early stage founders or non-experienced salespeople are pitching and only then they are going and asking questions. And I think that then basically they are giving a vanilla pitch that is less effective. Maybe the customer doesn't really have a pain and then it will only be a waste of CO2 and air giving the pitch.

Digital Rebels Consulting (05:51)
Mm-hmm.

Gotcha. Yeah. Like most things that takes practice. And if you're not doing it on a regular basis, you kind of have to figure out again, it's just like sports or, don't know, I guess you could use the analogy of riding a bike, but at the end of the day, if you haven't done it in a while, it's going to take you maybe one, two, three tries in order to figure out. mean, if you were to put me back into a role that I had 15 years ago, as far as just knocking on doors and doing that sort of selling, I probably wouldn't be good at it. But you know, if you gave me a few runs at it, maybe some, some coaching from somebody like you, or maybe some AI role playing or something like that.

It kind of just helps, ⁓ reconnect at least, ⁓ those activities in my brain. how do you teach them? How do you, how do you teach them how to, prep for those first calls? Do you just, ⁓ is it about prepping for their product? Do you teach them to do research on the company, a combination of both, or what does that look like in practice?

Raz Vicerabin (06:28)
Absolutely.

So I think that prepping for a first call is less about preparation on their product. I think if there is one thing that they know very well is their product and their space and probably they have founded the company because they know the space and they know the problem and that's what they came to solve. I think first of all is you asked about the mindset shift. So one is you need to prepare for a call. When I ask in my founders program, the founders, how many of them are preparing for more than five minutes?

for an intro call, probably like 10%. Most people all don't prepare or prepare for like few minutes, just maybe skimming through the LinkedIn of the person that they are going to meet. And I think that the important thing is first of all, invest time in prepping. AI can be a huge, something that will make much more efficient and fast to prepare. But I think that you need to research the company, you need to research the person, you need to try to find icebreakers.

and think that you can connect to the person. Try to read the news, understand what happens, what's the latest and greatest. Maybe the company is now going through like a big layout. You want to know this. You want to be mindful of this when you're going into those conversations. And I think that what I would also say when it comes to preparation, when we think about how much it costs us to get to a meeting with a qualified lead, probably it's between a thousand to three thousand dollars.

Digital Rebels Consulting (07:59)
Hmm?

Raz Vicerabin (08:12)
sometimes even more. So this is a very expensive and big investment that you make that probably worth at least 15 minutes of preparation and doing something structured and having a checklist of things that you wanna do before you go on a call.

Digital Rebels Consulting (08:27)
Yeah, I think that it's a good point there. Um, because a lot of those meetings, might not get another meeting. I mean, you might, uh, especially if you wing it and it's a good opportunity for you to, to find a solution for a particular problem. Um, if you don't do your due diligence ahead of time and you, I don't know, you, you screw it up. You might not get another shot. So I think, I think, I always think that prep is, is 100 % one of the biggest things that you can do.

⁓ to have more of an effective, I guess, successful meeting, especially if it's that first one, because obviously in that first one, it's not about the features and benefits, but it's also building trust. And if you, you screw it up or you wing it, or you just tell them something that they already know, ⁓ you could lose that credibility right up front. Maybe they're not, not get another shot. ⁓ you also teach at a university. So I'm curious if there's a difference between what you teach in the university as compared to what you teach in your, ⁓ your coaching classes.

Raz Vicerabin (09:22)
Yeah, so very much so. In universities, I think you have mentioned before that sales is not being taught in universities, which is true. I have like a bachelor degree both in law and business and an MBA from Kellogg and Tel Aviv Business School. was never, sales was never mentioned in any of the degrees. ⁓ I got into sales kind of accidentally and that's true also for most of my friends in the profession, at least in Tel Aviv. I wanted to try and change it. So I actually pitched to universities.

why they should teach B2B sales as part of the degree. And I think that this is, when you come to students, at least my aspiration when I teach or my goal when I teach students, I wanna change their image about sales. I want to share with them the notion that sales and B2B sales and B2B sales in tech is a fascinating profession that can really be in a super interesting and rewarding career.

And I need, but I need to keep it at the same time, a little bit more basic because at the end of the day, it's not that tomorrow they are going to run discovery calls and deals and negotiate. So it's kind of a combination of what are the, what's the knowledge that they can take from the course to the real life, because we are all selling all the time, but also exposing them to the profession of B2B sales. So actually very different than teaching entrepreneurs and founders who

want the value today, they want to already, if we are meeting in the morning, they want already in the meetings in the afternoon to be able to already implement things that will make them better, that will increase their conversion, that will shorten their sales processes, and so on. So very different.

Digital Rebels Consulting (11:01)
Yeah. And the coaching is important too. It can be rewarding career. It can also be a very frustrating one if you're trying to figure it out by yourself and you don't have the support of a university to teach you how to do it or a sales manager is too busy to support a new hire. ⁓ you know, but I think it's also why, you know, people like yourself and me, ⁓ can help, you know, guide those people along to have more success, to teach the things that typically aren't either sought out by themselves or taught in a university. ⁓

How long is your course? Just out of curiosity. Is it like a nine week, 12 week program, longer, shorter?

Raz Vicerabin (11:34)
very, very brief. not in weeks, it's two half days. Usually I run it like nine to 1.30, two half days, one after the other. I would have loved, by the way, to have the opportunity to run it for weeks. I think that the main challenge with founders is already to find two half days and 10 hours for them to invest and free in order to just gain knowledge. It's extremely hard. So I try to make it very condensed and very hands-on.

and very short.

Digital Rebels Consulting (12:05)
good idea. And I think you also do the one-on-one consulting as well. And I guess what's the difference between the one-on-one consulting and, ⁓ I guess doing the, group workshops.

Raz Vicerabin (12:14)
So I think usually what happens in one-on-ones is that you have the urgent things that every time you want to cover, whether it's like an important deal that is now in negotiation or a proposal you need to give or like a very important demo. And I think that, and then you are covering those things and you are helping and advising and the founders are learning as we go. But when founders are going through a structured program that covers everything from the first meeting,

to the close and how to do a pitch and the components of the pitch and the demo and the champion and all the relevant things and how to run a POV and what are the pitfalls to be aware of, they get something that is very structured. It's kind of, they get the map, they get the structure, they get the playbook, they see how the promised land should look like. It doesn't mean that it's going to be easy to implement it and to improve on their own, but they'll at least understand and get the structure. And then they can go after the program and...

start implementing and improving on things that they did before and investigate where they improve.

Digital Rebels Consulting (13:17)
One of the,

one of the other, I guess pillars of your coaching is negotiation as well. Cause that's one of the things that you teach. do you have any favorite, like a negotiation books or people that you follow or, ⁓ what was the inspiration for teaching negotiation?

Raz Vicerabin (13:32)
So one is going to be a bit cliche, ⁓ but it's like never split the difference and also with my background and also what I do in reserve duties, I look for missing in action like soldiers and being a criminal interrogator. So I think that Chris Voss, one, he's great ⁓ and super practical. ⁓ There is another person who I really admire, the way that she's looking and teaching negotiation. used to be my professor.

at Kellogg for negotiation, Lee Thompson. And I think that the main thing that she taught me was one, how important it is to prepare for negotiation, to have good structure, to know the frameworks in order not to wing it. And moreover, I don't know if you are familiar with the term Zopa, zone of possible agreement, but when most people believe, because that's what we see in movies, that you need to be

hard and protective when you come to a negotiation. And I believe that in most cases, it's actually the opposite. When you come open-hearted, when you are sharing with the other side, what's important for you? When you allow them to share what's important for them, many times what you are able to do is increase the size of the pie instead of focusing on who is getting a larger slice. And then eventually both sides are getting to a better deal.

And especially when we think about B2B sales, this is a long term relationship. You are going to be in bed with those people many times for years. So I think that my motivation was to teach negotiation in order one, to say there is also much more science than art to negotiation, but also to change the perspective that negotiation is me against you.

but more to provide the perspective that negotiation many times is if we are trying to collaborate in a way and get a deal that is better for both of us, we are both going to win and be happier at the end.

Digital Rebels Consulting (15:36)
What if you're in an industry, ⁓ where the people on the other side of the table are aggressive and they are being difficult with you. Do you tend to have that same mentality that you were just describing or do you match, guess their aggressiveness and their hard ball tactics.

Raz Vicerabin (15:53)
Personally, I'm trying to soften them, then adapting to their aggressive approach. I'm not saying that that's the only way to go about it, but at least personally, it's harder for me to be more aggressive. And at least what I kind of saw, if you think about it like a battle sometimes, sometimes when you will come to someone that has the armor and everything and the sword and the shield and everything, and you would come like David without like anything and say,

I come in peace, I want to do it together. I come without my, here my weapons are not here, nothing is here. It will replicate and they would actually see and say, okay, maybe we should take a different approach. And it worked for me many times in the past. I would not say in a hundred percent of the cases, but I've seen it work many times.

Digital Rebels Consulting (16:41)
Yeah, I have a similar mindset as well. ⁓ probably come it's better to come, guess, with a good intentions as opposed to, ⁓ you know, I don't know, bringing up a Zuka to a knife fight. ⁓ what do you see as far as, negotiation mistakes that, that founders make, ⁓ that you typically come up on your discussions with negotiation.

Raz Vicerabin (17:00)
So one I think is ⁓ focusing too much on the price. Many times when your prospect, your potential customer is asking for a discount or for a significant discount, there are other things behind it. Many times the value that is not established, the pain that is not big enough, the fact that you have not worked on like a cost justification well enough before. And then you kind of start to negotiate against yourself and reduce the price.

and then that's not even the issue. So I think that's a very common mistake and I think that when someone asks you for a very big discount, you should ask yourself things around your sales process less than the price of the deal itself. In most cases, not in all cases, but in most cases.

Digital Rebels Consulting (17:47)
Yeah. And I think once you get into that trap, as far as discounting at the end of a lot of negotiations, people on pick up on that pattern and you'll just continuing to lose and lose, especially if you're competing against other suppliers that are doing the same thing. ⁓ so it's not good for anybody. and there's just a habit that, ⁓ it's like, you know, my, my kids asked me for a cookie before bed. If I give it to them one time, they're going to expect it the next night and the next night as well. ⁓

How do you know when to walk away from a deal? Like when you're in a negotiating tactic, you're stuck on price. How do you know when you're just going to say, Hey, that's it. It's my best offer. I'm just going to walk away. Or do you continue to work with them?

Raz Vicerabin (18:25)
Good question. ⁓

I think that especially for early stage startups, one of the most important thing is understanding how much resources things are going to, like a deal is going to take from you. Because the most important thing for you and the most important asset is your resources, your people, the time, the focus. And if something is going to deviate you too much from your critical path, this is a deal that is maybe not worth taking. So I think it's a question everyone should ask themselves, but we don't need to take a deal.

At any price by the way, it's not only a question of price It's also a question of what commitments are we making maybe we are getting a price that we want But we are making commitments that are going to be very hard for us to actually meet and if we are going to meet them It's going to ruin our roadmap sabotage many other deals our progression. So I think that those are the questions that are important to ask and when deciding whether we should Try to take and win a deal or not

Digital Rebels Consulting (19:23)
Gotcha. It makes sense. ⁓ and when, I guess, with these, founder led companies or say, lot of companies that are scaling, ⁓ what are some of, what's the best time to hire their first salesperson? At what point does it go from a founder led sales to I need to hire for a salesperson, need to hire VPS sales. When's the right time?

Raz Vicerabin (19:43)
So overall I agree with the rule of thumb that is saying that when you get to like a million dollar ARR, maybe we can lower it to even half a million dollar ARR depending on the ACV and the number of deals that you are running. That's usually like a good time and before this it's like too early. And if I'm trying to not look only at ARR, so I think that it's when you start to, I would not say having like a repeatable sales process, that's I think way too much to ask in order to have, or way too high of a bar in order to.

require for the first sales hire, but you need to understand why you are winning. You need to be able to break your sales process into something that is relatively structured, and you need to understand why your prospects and your customers are actually buying. So this is something that you will be able to teach other people and also give them a product that is already sellable. So I think that that's probably the right timing to do so.

Those are the two main factors that I will take into account. The ARR that I have, number of deals, and how explainable both the reasons and the sales process, for the customers to buy and the sales process structure

Digital Rebels Consulting (20:54)
sales metrics do founders typically focus on that they might think that they're doing a great job and they're actually bad metrics to follow as far as just thinking that they're scaling in the right way.

Raz Vicerabin (21:05)
So I think that many times founders, especially early stage, are measuring the size of their pipeline. And I think that this is probably a wrong metric to look at because when you have early stage opportunities that you project and believe that will be relatively large but they are very early on, this is not indicative because you don't know yet what's going to be your conversion. And probably the right metric is not only the overall conversion but the conversion between

between the different stages of the pipeline. And that's where you will actually be able to identify challenges that you have. And maybe like a small tip here that I find very, very important is to build your CRM in a way that you will be able to measure the conversion between steps and not changing it too often because then it breaks your ability to actually measure the conversion between steps. Because seeing where your conversion drops between steps in the sales process,

is something that can teach you a lot about what you're doing well and where you actually need to improve and what you all need to work on. So I think it's not the size of the pipeline, but the conversion overall and the conversion between stages that is the right metric to look at.

Digital Rebels Consulting (22:16)
Do you ever have conversations with founders as far as that pipeline management and why deals get stuck in the pipeline? Do you have an opinion as to why deals get quote unquote stuck?

Raz Vicerabin (22:25)
So most of my time is actually conversations around those things. But I think that when we think broadly about where deals get stuck, that's what I call the two cemeteries of the pipeline, the two opportunities cemeteries. One dwells after the demo and before you actually manage to move it into like a POV, a proof of value.

and one usually dwells after you are conducting a POV and then, it takes very long in order to actually convert it, or it just dies after the POV and you never manage to close those deals. And there also very good reasons and relatively simple things that can be done in order to avoid those two seminaries.

Digital Rebels Consulting (23:09)
⁓ What are the simple things that can be done?

Raz Vicerabin (23:13)
So if we start from the second one, so I think like the cemetery that dwells after the proof of value, the solution is not what you can do after the proof of value. The question is, what alignment have you done before you actually enter the POV? And who did you get the green light from entering the POV? So generally, you need to do two things. One, you need to align with your prospect, with your champion on the success criteria and define well your success criteria.

agree on the level of effort that is required and talk about commercials, even if it's in ballparks, but talk about commercials before you go into a POV. The second thing that is ultra important is preferably meeting with the economic buyer, running all those things with the economic buyer and getting the green light from the economic buyer that if all those things are going to be met and success criteria is going to be met, one, you are going to have a deal, two, you will understand what is the timeline to actually convert it.

Easier said than done, by the way, not always it's easy to get in front of the economic buyer, but something that is at least a must is even if you don't manage to get in front of the economic buyer, is to ask your champion to run those things by the economic buyer, get the green light from the economic buyer to move forward. And even if the champion was your mouth and ears in this situation, you know at least that you are not going to have surprises later on. And someone with the budget and with the authority,

Have approved going into this POV and is taking it seriously. So that's I think one

The other one is the post demo. And I think that it's very hard for most sellers to get to the next step after the demo. And one of the main reasons is you have shown your prospects almost everything now. They understand the product, they saw how it looks, they believe that they understand the value that your product is giving, and definitely they understand the problem that they have. So they don't need anything else from you.

So usually the way that demo meetings end is great. So we will discuss it internally and we'll get back to you. And then crickets, and then you follow up, and then you follow up and you say, don't understand. There were like great indicators, the pain was there, they loved it. They said this is very interesting, super interesting solution. And then we never heard back from them. So I think that one is preparing before the demo meeting and trying to think what is the next step that you wanna have.

after the demo meeting that you are able to book at the end of the demo meeting, that will be easy for your prospect to say yes and not go black on you. My suggestion for this step usually is saying, okay, so it seems that it's interesting and relevant. I know that you are not yet in a position to say, yes, I wanna do a proof of value, but is it interesting enough in order to explore the option of doing a proof of value? And then most of the times they would say yes.

Digital Rebels Consulting (25:51)
Mm.

Raz Vicerabin (26:10)
So then what I would suggest as a next step is what I call a POV alignment. So let's align on what's required from our side in order to do a POV, what's required on your side to do a POV. Maybe you schedule 15 minutes just to do those things. And then we will both have all the information needed in order to actually make the decision whether it makes sense to move forward with a POV. And the thing with the POV alignment framework is that it allows you to open other tracks.

So the POV alignment framework is what we discussed before, right, on how to avoid the second cemetery, which is agree on success criteria, discuss the level of effort that is needed, what integrations, how many people, how many times, and so on, and ballpark of commercial, so maybe even giving an actual proposal. Once you are aligning on those things after the demo, then it opens three tracks, right? Now you need to have a meeting in order to discuss success criteria.

Now you need to have maybe a technical meeting in order to understand the level of effort of doing a POV. Now you need to collect metrics in order to provide a proposal and suddenly you gain deal momentum and the deal doesn't stall. So when you manage to jump above this big hole in the ground, which many opportunities fall into, which dwells after the demo, you manage to gain this deal momentum and in many cases, skip the cemetery, the post demo cemetery.

Digital Rebels Consulting (27:35)
That's a good advice. ⁓ and I imagine that you've learned a lot of things over your career as far as selling, cause you've been doing it for quite some time. ⁓ is there anything that, ⁓ you used to think was the foundation of great sales, maybe 10, 15 years ago in your career? And I guess what are your fundamental beliefs now as far as what makes great sales people.

Raz Vicerabin (27:55)
So if I need to pick one trait, one characteristic that is the most important that I'm looking for in a salesperson is curiosity. And I think that it ties to the most important thing in my view in a sales process, which is the discovery. Running a good and thorough discovery is not something that can completely be taught. Meaning it can be taught, but it's not that you are going to have like a checklist of questions and you are going to...

tick each one of those questions and then you have a great discovery. You need to really be curious. You need to always ask why. You need to always have question marks. And I think that that's one of the things that I didn't realize 10 years ago. The discovery is the most important thing in order to have a successful and a solid deal. And the way that I at least view discovery is if we think about a deal as a building, discovery is the foundation.

If the foundation of the building is not strong enough and not solid, at some point the building will collapse. Maybe it will collapse straight after the first meeting because we didn't even get to the point that we identified the pain and now the prospect is not interested in continuing the conversation with us. And maybe it will collapse after the proof of value because we have not identified the right stakeholders and we did not understand the buying process well enough in the discovery and now...

we are kind of lost in the deal.

Digital Rebels Consulting (29:24)
Lots of great tips there. Um, let's pivot over to our burn it or build it rapid fire segment. I'm going to give you 10 topics, typically hot takes and sales and marketing, um, for founder led sales, sales and marketing and businesses today. So I'll throw out a topic. You tell me burn it or build it. Are you ready?

Raz Vicerabin (29:44)
Let's do it.

Digital Rebels Consulting (29:46)
Number one, founder led sales until a 1 million ARR.

Raz Vicerabin (29:51)
So build it with a caveat, but that's something that we discussed earlier. But at the end of the day, think that founders need to...

need to sell themselves until it's relatively repeatable and they can explain it. At the same time, I would say, since I work with many cyber startups, the pace is much faster there. And many cyber companies are under a lot of pressure to hire salespeople and to grow because a lot of money is being invested. And cyber is more like Formula One, where everyone is chasing and there is only three places on the podium. All the rest will die.

So I think that there is a caveat there that with cyber companies, many times they will hire or need to hire much earlier than the $1 million ARR.

Digital Rebels Consulting (30:36)
Gotcha. Number two, teaching selling to non-sales people.

Raz Vicerabin (30:40)
Build it also with a caveat. So I think that it depends. If you need to run fast, if you are an early stage startup, you are not able to hire non-salespeople, teach them. It takes too long, the risk is too high. And by the way, I've done it, I've tried it and I failed. When you are an established company, I think that talent is more important than ⁓ experience. And I think that many times,

taking people that has experience but has bad habits is bad and it's impossible to change their bad habits and bringing very talented people in, teaching them how to sell. Working with really good enablement team is an incredible way to build a very strong sales team and something that I've seen firsthand that we did at Reskified in the Tel Aviv office. We hired only non-experienced people and...

In six to 12 months, we build sales monsters, people that were able to run millions of dollars of deals, and it was super complex because they got the right guidance and they were super talented and skillful.

Digital Rebels Consulting (31:53)
Yeah, I think it helps to have some cross-functional understanding of how everyone's job is kind of intertwined. So you're all kind of rolling in the same direction to understand internally. Uh, everybody's like it's pain and processes and what they're up against. think it helps you develop better products, market better products, and then sell them better. Cause everyone kind of understands how the team is working together or at least should be. number three, revenue growth over sales process.

Raz Vicerabin (32:17)
Burn it. I think that if you don't have a good sales process, you are putting your revenue growth at risk and is being jeopardized because it's kind of, I would not say it's luck, but it's not something that is totally explainable. And then at some point it can break. And when you are already in a very good like revenue growth trajectory and suddenly something breaks, it shakes the ship much more.

And I think that building a good foundation and a good sales process and then building the revenue growth that is based on a good sales foundation and sales process is something that is much more scalable for a company and healthy for a

Digital Rebels Consulting (32:57)
Agreed. Number four, cold calling as your primary strategy.

Raz Vicerabin (33:01)
Burn, but I love cold calling. So I think that the only thing that I would change there is as your primary strategy, like cold outreach or outbound strategy. I think cold calling is super effective, but it should be one of the channels for developing and creating top of the funnel and not the one thing to rely on. ⁓ And for the audience, if you are not familiar with a book called Cold Calling Sucks, this is like a super recommended book and in like two sentences it basically says,

Cold calling sucks, yes, cold calling sucks. That's why it's effective because no one wants to do it. And that's your way to go above the noise. And it's based on like 300,000 calls that we'll analyze through Gong. So super practical and recommended.

Digital Rebels Consulting (33:42)
Yeah. Multi-channel.

I was going to say multi-channel strategy is usually good. You can't put all your eggs in one basket. speaking of eggs in one basket, number five, some people do this AI automated outreach.

Raz Vicerabin (33:48)
exactly.

Definitely build. I think that if we are looking at the way that AI is ⁓ impacting and is going to impact sales in the coming years, outreach is probably the main one. I think that it will take time until AI will actually modify dramatically the first meeting to closing. But in everything that is outreach related, there are incredible tools now.

and that are AI, SDRs, automations, customized campaigns and messages that it's foolish not to use them now. So definitely worth doing.

Digital Rebels Consulting (34:34)
Gotcha. Demo first, sales calls.

Raz Vicerabin (34:37)
So definitely burn it. In my view, in most cases, there are exceptions, but in most cases, you should not run a demo on the first meeting for two main reasons. One, the goal for the first meeting is get to the second meeting. When you are not running a demo in the first meeting, but talking about I'm going to show you a demo if we have time, but manage your time in a way that you not going to have time in order to run a demo, it makes it much easier.

to book the next meeting to create the momentum because your prospect is actually excited to see the demo that they did not get the chance to see yet. Two, it gets too technical too soon. The first meeting is not about technical things. It's about the vision, it's about the value. And demos tend to get very technical. So I think that in most cases, my recommendation would actually be don't do a demo on the first meeting. And maybe last is that when you are, the first meeting is focused mainly on the discovery part.

When you are running your demo on the first meeting, it means that you are going to run relatively vanilla demo. You are not going to implement everything that you have learned in the discovery into the demo. And your demo is going to be much less impactful, which is the third reason for why running a demo on a second meeting is probably more effective and a better way of doing things.

Digital Rebels Consulting (35:55)
tips. What about anchoring high early in negotiation?

Raz Vicerabin (35:59)
If you have built, so build it in our game, and I think that if you have built the value and if you have worked on building a cost justification and you understand how prospect is buying, you definitely wanna anchor high in the negotiation. What's I think important when you anchor high is to think about what I call the pricing ladder. Let's say you anchored high.

You offer the deal for 200,000 that maybe will eventually close at 80,000 or 100,000. You need to have good explanations how you're going to go down from 200,000 to 100,000 without your prospect feeling that you tried to rip them off before. And in order for this to happen, you need to do preparation and you need to build your pricing ladder. For example, saying before even you give the proposal, our relationship is very strategic for us, this is a new segment for us, that's something we really wanna.

penetrate into we believe that working with your A team is going to improve us a lot and help us build our roadmap etc etc and then you will be able to make price concessions in a justifiable way.

Digital Rebels Consulting (37:05)
Gotcha. And it brings us to number eight tier discounting to create goodwill.

Raz Vicerabin (37:09)
Burn it, definitely burn it. Which also ties to value, right? I think that at the end of the day, most price negotiations are not around price, they're around value. ⁓ And I think that most buyers are not appreciating discounts as goodwill, and they will take advantage of it. There are exceptions, of course, but in general, I think that if you need to make too big of price concessions,

You need to try to pivot it into understanding what the prospect is missing about the value that your solution is going to provide before you are going and continue to negotiate.

Digital Rebels Consulting (37:43)
Yeah. One of those exceptions, which brings us to number nine, discounting for big name logo. So there's big companies you want to discount just so you can say you did business with Google.

Raz Vicerabin (37:52)
So if I need to pick between build it or burn it, I would say build it. But you need to be very careful with it because this is a slippery slope. At the same time, not only for early stage startups, also for more mature companies, big logos are very meaningful. ⁓ And it's really helpful and it creates a lot of credibility. At the same time, big logos usually come with deep pockets.

And if your product is going to give them value, they're to be able to pay for this. So I think that you definitely don't want to jump too fast in order to give like big discounts. But if that's the way that you are going to win the deal, I would not walk away from the deal with a large logo because eventually they negotiated a very good deal for them. But I would try to be very careful.

with it and at least one of the things that I say many times when I get to this situation is I try to tackle it head on and I say to those, and I've sold to many large organizations whether it's Walmart or H and Booking and American Express and I was like a 20 people, 30 people startup out of Tel Aviv, right? And I think that when you are saying, guys, it's important for me that we will focus on the value and I know that you are the giant and I'm the dwarf but I would really appreciate it. I'll give you a good deal but.

I would really appreciate if you will not crush me in this negotiation and understand that there are also things that I need to bring back to the board and it will look extremely bad if I will bring like a very small deal from American Express or from Walmart to my board, it will look really bad. So let's try to work in a way that you will get value, but it will be a fair deal for both of us that will be productive and we are building here a long-term relationship. And I think again, it goes to the conversation we had before about...

going to the fight and sometimes, you know, putting the... coming without an armour and everything. And when you allow people to be the bigger person, many times they take this opportunity and they don't take advantage of their strength.

Digital Rebels Consulting (39:56)
And that brings us to number 10, taking advantage of people. what do you do, uh, burning or build it walking away from low ball offers?

Raz Vicerabin (40:03)
One, I don't walk away that fast, but I also don't agree to lowball offers. I think that I will try to pivot the conversation and I think I needed to say before whether I build it or burn it. So I would say that I burn it because I believe less in walking away, but I would try and usually when you get to the point where you are negotiating and there is an offer, you have invested already a lot of resources in this deal, but I will try to understand what's behind it.

and try to pivot the conversation there. And then I will decide if it's a global offer and I feel that I'm weak in the negotiation, but it's a good deal for me, I will take it.

Digital Rebels Consulting (40:41)
Makes sense. We're just about out of time here today, but you get the final word. Give our sales and marketing leaders one piece of advice that they can walk away with and implement today to accelerate their sales process.

Raz Vicerabin (40:52)
alignment before entering proof of value, making sure that you have a real deal, that you have a champion, that you have a green light from the economic buyer, and only then enter the POV, because otherwise a lot of resources are going to be wasted. Team morale is going to be hurt dramatically when you are going to lose those POVs, and it's very hard to recover from those things.

Digital Rebels Consulting (41:14)
Good tip. And where can people find you and learn more about wings?

Raz Vicerabin (41:18)
So on my website, www.sells-wings.com, and you can find information about the program. And also I'm coming to New York City very soon in order to deliver the first sales program for founders outside of Israel on the first week of February.

Digital Rebels Consulting (41:36)
first week of February and we'll put the link in the show notes and appreciate your time today, Raz.

Raz Vicerabin (41:41)
Thank you so much, Mark. Appreciate it.

Digital Rebels Consulting (41:43)
All right, cheers.

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