Avi Wiesenberg, CRO and Start-up Advisor

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As one of the prominent start-up advisors in Israel, Avi is always happy to talk to sales. He cut his teeth at Oracle, one of the strongest sales-first organizations in the world, and has gone on to advise dozens of successful start-ups on their commercial strategy.

Full of wisdom, advise on resources, and commercial brilliance from a dedicated sales savant, this is more than worth a read (or listen!).

You can read Avi’s full biography here


Jamie: Avi, when you think back on your sales and sales mentorship career, what have you found most fulfilling thus far? 

Avi: I think in terms of my career as an executive sales leader- and I still define myself as a salesperson – I think the most fulfilling piece of it is building value on both sides. It is building value for the companies that I am working for – products that I am selling, and building value for the people that I am selling to. It knows that I have a solution, that I have a product, that I have something worthwhile for the person at the other end; and that can drive their business forward generally.

My entire career was focused on B2B sales. Primarily, enterprise-wide sales, but then later, I branched into mid marketing small business sales as well. It is usually being in that technology arena, in that technology space, wherein essence it is usually a solution sale or technology sale; it’s all about the value other end is getting.

What I find fulfilling is learning other people’s businesses, and learning how and what I am providing to them, which will, in essence, change or add value to the way that they do business.


Jamie: Can you talk about how essential it is that the salesperson understands the business of the person he is selling to?


The number one thing I look for in a salesperson when I hire them is business acumen; as in sheer curiosity. It stems all the way from, “Are you interested in what is going on in the world of business? Are you reading business pages?” all the way through to when you have a conversation with someone, “Are you genuinely interested and curious?”

I think curiosity is essential to understand how the business works today, that status quo, how they do their job today and how they do at that arena. Then, tying together with your interests. I am not saying you have to be completely passionate about what you are selling, but I think you have to understand that there is a value in at least having an interest in what you are selling, and then a deep interest on the other sides of the business. I think the other side in terms of commercial curiosity and business career is probably a more essential piece of it, because you want to understand how and what you have got, and therefore help them continue their day-to-day in the way they do business.


Jamie: Do you think that is essential in just B2B sales, or to B2C as well?

Avi: When I look at B2C, I think it understands the real need. What I do today, in the evolution of my career, has been derived from that sales consulting arena, where I am working with a lot of different startups and helping them drive their businesses forward.

The number one thing I always ask is, “Do you really understand what you are selling?” The example that I very often give is ‘Amazon Alexa’. I bought an Alexa. I am not quite sure why, and when I asked my wife, who is an accountant, I said, “I want to buy this thing.” She asked, “Why, what do you need it for?”

“Well, it is really cool. It plays music, you have got speaker on, you put this or that.” The only way I ended up buying it was on Amazon Prime Day where it was on discount. You can use discounts to push people through and make them feel like they are getting involved. Discounts are a sales technique, and I think it is that ability to understand what it is that you are really selling.

If you are selling a property, “Are you selling a property, or are you selling an investment? Are you selling a home for someone to live in, or are we selling the dream of raising their family? What is it that you are really selling to that other person?”

That discovery, that curiosity, that understanding of the person on the other end of the call and the ability to drill down two or three levels deeper, which I think you have to have some level of enjoyment and being able to kind of say, “Yes, I got it! I got what they are actually interested in, and then I tied my sale back to that.” That gives me a lot of satisfaction.


Jamie: How do you go about getting that information and choosing which need you are going after, if the clients or the prospects are being quite difficult?

Avi: There are a ton of different techniques. To be honest with you, and this is what I think I found quite revolutionary, this is something which is barely ever taught –

I did a business degree, and sales was not tight, right? There was no sales 101. I think maybe universities have started doing that now, in the business degrees and the MBAs, but sales was not respected as a profession or as a type of science, I think.

I am saying that in the tech world, a huge number of technologies are now coming in to build the scientific approach into sales. My wife works for a company called ‘’. It’s worth having a look at them, Gong basically records sales calls and analyse them. It tries to build up an understanding of the momentum in the deal, which deals are going to close; and how much you are speaking vs. the client speaking. They had a fascinating example where they found that swearing a little in a sales demo leads to a higher close rate, but swearing too much does not. Today you have got that ability to really crunch the numbers and the data, and there is a huge amount of scientific research to being done into what we have always felt is true. “Was it a little bit of an art, rather than a science?” I usually ask that question, “Is sales an art or a science?” and I think that it is still a mixture of both. If you are studying business, it is an MBA, it is Bachelors of Art, at the end of the day; but I think there is a lot of science that was built into it.

Your question is, “What methodologies and techniques do I use when you are not getting that information?”

The first formal sales training I ever had; I think I had one of the best sales schools out there, which is why I started my career at Oracle, the heavily sales-driven technology company. You can get technology companies with product-driven marketing strategies, or sales-driven culture.

I knew that I wanted to be in technology, and I went from selling ice pops outside the house all the way to learning proper sales. My father sold in the East end of London.

Learning to sell in that capacity in a more wheeler-dealer commodity-type sale was always something that was part of me, but I was always passionate about technology. I enjoyed it. It is something I knew I wanted to see in my long-term career, but I did not realise that I wanted it to be in sales until I joined a proper company. I understood that I am not a developer, and I am never going to be a developer, it does not excite me; sales drives these businesses. You want to be in a business that sells well, right? The business arm of that business ultimately is sales. I realised that “To Sell is Human” way before Daniel Pink wrote the book. I love that book. I think it is a phenomenal book. He says every conversation we have is a sales conversation.

Going back to Oracle, Oracle gave me the training to understand the methodologies; and the fact that you can be very methodological in the way you have these conversations, basically, you are running things. At the base and I still think it is nearly over 40 years old now, but for me, Neil Rackham’s “SPIN Selling” still sits as the fundamental basis to sales. I think there is a huge amount you can evolve on top of it. You can add the “Challenger Sale” – Brent Adamson and Matthew Dixon. You can add a whole bunch of things, but for me, that foundational layer is a SPIN-selling layer because it deals primarily with the premise of the status quo, “How are you doing what you do today? What is the actual problem of paying or implied paying or direct paying in terms of how you are doing it today? Do you even think you need to change? What are your implied needs?” Only then can you start having a conversation about the need to pay off. You can throw in a ton of techniques all the way from Chris Voss’ mirroring to loads of other stuff.

There are a range of ways, but ultimately you have got to build that trust. You have got to start by building that trust, and then you have got to have an open conversation. Today, what I think has become very prevalent in sales is; I would not say you are ever going to be a trusted advisor status. I had this argument 15 years ago when I got promoted inside Oracle, and

I remember my promotional interview with the head of the UK organisation, we had an argument about whether you can ever become a trusted advisor to the customer. I argued, “No, they will never trust me to run the business because they know I am coming at this from an angle, that I want to make a deal; but they should trust me when it comes to Oracle.” I am the person that understands Oracle better. I am their conduit into it, and ultimately you are a middleman. You have to make the deal happen.

You have got to play both sides and get the two parts to marry. I think SPIN comes as a basis of it. Then, you have to go from there. You have got to build that trust to have that conversation about how they do it today and whether they have any problems with that.

Avi: It is a very different sale to Dimitry Toukhcher’s fashion and suits, but I think he understands he is not selling a suit. He is selling your next deal. He is selling something way more than just clothing.


Jamie: What made you want to go into tech?

Avi: I actually wanted originally to move to Israel. I am Zionist. I wanted to come out here. I know the Israeli tech scene was the only way to make a half-decent living in Israel. I was always fascinated by technology. I was the guy who was fixing everyone’s printer. I love gadgets. I love toys. Tech, for me, is exciting. This is changing the way that we live and work, but I really did not understand that. I mean, when I appeared for my interview at Oracle, I had no idea what database looks like and the irony was back in those days, there was an information systems module within my degree where you had to make our Excel spreadsheet. I had a website built in Dreamweaver. I did not understand how the internet works. Oracle is a back-end technology company. 

I think the second you started to understand that, you take the red pill and you go down that rabbit hole, and you understand how deep this goes and how much is underlying underneath that, you start going, “This is what was really interesting in terms of the way the world runs.” I think it was that passion for the future, in essence.


Jamie: Okay, would you recommend then that any salesperson go into tech?

Avi: No. I think you have to go into something that you are somewhat passionate about. Listen, I do not believe in, “Work for what you love and screw everything else. You should just follow your dreams, and there are happy rainbows at the end of it.”

We have all got to make a living, and life is not all fairy cakes and stardust. There is a hard graft that needs to be done. You have a certain aptitude, and you have to be realistic with yourself. If you are not good with numbers, you should not go into selling stocks or investments. You are going to be blown away when you try to talk about the ROI and everything else. You are going to struggle with that. Do not get me wrong, I have had three arguments in the last six months with highly tech-focused companies, one of them in Quantum Computing where I kind of said to them,

“I failed physics A level, right?” and he was like, “Well everyone in the company has got a PhD in physics. I do not think you can help with our service.” I said, “Mate, I am not going to do the technical side. Someone else has to do that. There is a whole other element of the sale that you guys do not understand, which is the human side of the sale. The commercial side of the sale is completely different.”

 Can you learn it? Yes. Are you interested enough in the product? Yes, if you can convince yourself that you are interested enough in it, that is good enough; because you are going to have that level of passion. I go back to Daniel Pink, it is one of my favourite sales books, the ABC, within his redefined ABC of ‘Attunement, Buoyancy, and Clarity’ is buoyancy. If you are not going to be able to dialling’ and keep going on it; not saying you have to absolutely love the technology or product you are selling, but you have to have some interest in it. I think otherwise, you are going to really struggle when you get knocked down and carry on picking up the phone and ‘smiling and dialling.’

Jamie: You mentioned that you really benefited from going into a sales organisation instead of a marketing-led organisation. Would you recommend prioritising this for an aspiring salesperson?


That is a really interesting one because the world has changed so much. I think there is a huge benefit in starting in a sales-driven organisation because they will be investing in their sales team as a USP. They understand that they will win or die as a company based on how good their sales execution is, and that means they are investing in their sales team, as opposed to a company that is only investing in marketing or only investing in the product.

Now, I think today most tech companies and startups, etcetera, have an appreciation that it is holistic. They understand better the interconnection between marketing sales, its products, and marketing and everything else.

We have not even talked about the evolution, whereby there are plenty of tech companies that now up-and-coming are refusing to pay commission. I mean, one of the biggest examples of it, and I am fascinated to see if it will change as they evolve in their enterprise sales phase, is a company called ‘’ They are a pretty well-known Israeli company, focused on project management. They did a brilliant pivot actually, and I have a huge amount of respect for their marketing and what they build, but I am fundamentally and principally opposed to not paying salespeople commission. I do not believe in it. There is a huge perception within some organisations from non-salespeople that, “Hey, you are getting paid on this deal, give me a bit of your commission off to this deal closed because I helped out on it as well.” To which I would reply,

“Hey, that is my salary. It just happens to be that my salary is very heavily geared towards performance as opposed to you, and you get paid whether you deliver or not.”

‘’ – I believe that they built their playbook perfectly. This is the argument that there is an evolution coming concerning sales and product- or growth-driven sales, especially in B2C.

Elon Musk is selling satellites into orbit on a website, right? You can sign up online and send a satellite into space with the options there, all by clicking. If you’re product-driven, marketing-driven, the salesperson is just the friction, right? That is coming in, and I fundamentally agree with it up to a point. I think there are always those people who will want to deal with the person.

I also agree that the whole future of AI and where people are thinking is that those types of sales conversations can be happening through AI. Let us be brutally honest, the person-to-person connection is unnecessary in a pure-play commodity sale. There is a difference between going into a court kiosk or Corner Shop and buying something from a vending machine, right?  Let’s just buy it from a vending machine! Restaurants have been going in very much in that direction, right? Kiosks are becoming a huge area within a restaurant, especially for transactional fast food.

But I also don’t believe that you are going to go to a high-end restaurant, where you are sitting down for an experience, and order through a kiosk. It is not going to help. You are going to want the service. You are going to want to speak to the waiter, and you want to ask what is good. They are going to ask you what you are in the mood for. They are going to assess you to, and get to see who you are. You are going to say, “I like this. I do not like this.”

You know the difference between when you have had a good waiter. A good waiter tailors the conversation by asking perhaps two or three different questions. “What brings you here this evening?” and “Oh, it;s our anniversary,” “Well, let me recommend this special bottle of wine.”

That is a completely different engagement with just one situation question; that is sales, right? Yes, we may get to the point where technology can do that. That is not going to be for many years. I think that element of the sales process is not going to disappear anytime soon. I think it is fundamental.

Do I recommend being in a sales-driven organisation? Yes, because I think there is a respect whereby they understand that is the way to drive the business forward. Now that does not mean you are not going to get support; you are not going to get respect; with marketing-driven companies. I just feel there will be more expectations on you to be an industry specialist in marketing-led industries than it is to be a sales specialist.


Jamie: In terms of skills, what you will see and valued more in the modern salesperson, and what are those skills that you recommend salespeople and develop the most?

Avi: There is a difference between the skills that I think are going to set you apart in terms of your performance; and the skills that people are potentially looking for in technology sales.

To give an example, Mark Roberge was the Chief Revenue Officer of a company called HubSpot. Hubspot, in essence, is a CRM primarily aimed at the mid-market in SMB. He wrote a book called the ‘Sales Accelerator Formula.’

He built very clear things around sales training, and the skill sets that he was looking for, which made a good salesperson. For HubSpot, the same set of skills that were there for an Enterprise sales person was no longer there for a mid-market salesperson. For midmarket, they were potentially looking much more for coachability, for people that would follow their playbook and follow their scripts.

For the largest accounts, they were looking for the mavericks who were at places like IBM and Oracle and knew how to sell million-dollar deals. For the smaller accounts, they wanted people who could close $30,000 transactional deals. I think the first question you need to ask yourself as a salesperson, “What does my career trajectory look like? That is the first question I would ask. “What do you want to be when you grow up? Do you want to be a career salesperson?”

By the way, I think there is no problem with career salespeople. I was super young when I was promoted through the ranks. I started my career in inside sales running deals that are around $20,000 to $30,000. Back then, with Oracle, I sat in an office in Dublin selling through WebEx. I supported five sales reps in the UK, who were field sales reps; those were the big guys buying new BMWs every time they closed a deal, and I was the little guy sitting in the office in Dublin. Every time, there was a deal that was below $50,000, and eventually, below $100,000, that was my deal to run.

Within a year and a half, I was promoted through enterprise sales in the UK, running financial services accounts. These were big deals, and I was working in the city of London with career salespeople. The sales people who I worked with, they were earning more than their ‘boss’s boss’s boss’ in Oracle because if you smashed through targets, you could earn loads.

My belief is that if you are selling a $100,000,000 deal into Vodafone, if Vodafone is going to bet on Oracle to build the future of their company and invest $100,000,000; you, in essence, need to good enough to be sitting on the board. What does that mean? You have to understand Vodafone’s business as well as someone who is sitting on that board of Vodafone.

Not only you have to understand it better but also have got to understand the intricacies and the politics of getting this deal signed off. Now do not get me wrong, there is a holistic play that is going to go in there, multiple projects, and different people. There are a lot of moving parts to gain a $100,000,000 deal signed off, but ultimately you then ask, “Why is this sales guy being paid so much money?” Because he is at the top of the game!

“What skills do you look for?” you asked. For me it is the mentors. I did not have that many formal mentors, but in almost every company that I have joined, there have been people there who are willing to give you time if you ask but do not forget that you have to ask. No one is going to invest hours with you, but it was attending those meetings, speaking to those people, and asking for their advice –  what makes them good, and how to develop. It is much easier when you are younger than when you start growing in that career.

One of the best pieces of advice I was given was by my ex-Oracle colleagues, a guy called Gavin Dimmock. I was a young, cocky Jewish sales guy at Oracle. He said, “This is the same as your dad’s shmatter (fabric) business. The nice side is we are giving you a base salary, and we are giving you a phone, an office, and a laptop. Those are your accounts. Go and make yourself some money.” It is a franchise, and you run your own business. That is the attitude of a sales-driven company.

Wherever you have got a good company, a good product, and all the pieces of the puzzle are working, people get on with their job and make a lot of money. Your challenge today, because there is an element of the sale that has become more transactional, is that people say, “I do not need to pay these guys hundreds of thousands of dollars because there is a playbook. If the playbook is written, then, in essence, you are just a cog in the wheel. Do ‘X’ at this cadence, and you get ‘Y’ result.” That is a reason, to a certain extent, why commission is potentially being reduced some of these companies; they are pushing it out of the business because they are saying, “I can now measure literally everything that you are doing.”

“I will find where you can do better, and I will tell you to work harder or tell you to run the playbook better. I will train you, I will coach you, I will enable you or I will fire you. Assuming you are playing the playbook at 80%, now, by the way, you can play the playbook better, and do your own thing. I will see what you are doing better, because you are not working as hard, and you are getting the same result. So, I will get everyone to do that, and ten add it the playbook because clearly, it works.”

If that is your equation, then why are you paying commission? Because I should get 80% of what I need, assuming those two are in balance, right? That is the logic of why commission is being reduced at some companies. They will pay you your OTE, but they do not need to pay commission. Now, I believe the commission also kicks in when people hit their numbers early. You want to motivate them to do even more work, earn more and go back to the drivers, the skills, and the characteristics, and ensure that the competitive nature is still there in sales, right?

If you do not have that – it is still going to be some element of driving your will to win? Do you want to win in business? People want to win. It is there in every soap opera drama. You can ‘gamify’ and make other ways of winning other than pure commission. A lot of what I have said is that argument in terms of the shift from where sales was, which was very much franchise: “Here is your territory, go make some money.” All the way up to the other end of the spectrum, which is, “We are no longer paying commission, and we want highly industry-focused specialists.” I have seen brilliant startups in Israel grow with young, hungry, industry-focused, very smart professionals, who in essence are customer success reps who are working with the customer to get them value and helping the company.

All of this change has come about because of the internet. Today, you can do all that research. You can speak to everyone who is using the product. You pretty much know what you should be paying price-wise; unless you are at the high-end of complexity on sales. Now, for the sales rep, we go back to that question, “What should you focus on? What do you want to be when you grow up?”

 “I want to be a career salesperson at the top end of the enterprise B2B game,” for example – I know guys who sales guys, and they have been sales guys for 30 years. They sometimes, some years, will out-earn their ‘boss’s boss’s boss’. Every time they close a deal, they are going to buy a new BMW. Now, to be honest with you, those guys do not exist as much in Israel is not a big local domestic market. A lot of them are hired outside of Israel pretty quickly, but in the US and UK, you can be on really nice salaries. To do this job, you want to be able to navigate enterprises. You want to understand what is going to make an executive make that decision based on your technology. You want to try and focus on understanding technologies that are going to be big-ticket items. Long sales cycles, complex sales, big-ticket items, and focus on your sales skills and your competency at selling at an executive-level.

If you want to make yourself future-proof, I would say that the skills that you want to work on is understanding the sales funnel incredibly well, and understanding the maths behind it. How many leads lead to how many opportunities? How many opportunities lead to closure? Playing those numbers; understanding the cadences; understanding the mathematics that is behind it;

being able to understand what elements are your company is looking for; potentially picking an industry that you want to specialise in, whether it is sales, whether it is fashion. It does not make a difference what it is, but be the best in that; because there is an element today whereby your speciality is becoming very definitive of who you are, and people are able to find niches.

Your Instagram just becomes everything to do with that. Your LinkedIn becomes everything to do with that. You are just going to post on it over and over again. Someone says, “Hey, I need to talk about widgets. Oh, yeah. This guy is the world’s greatest expert on widgets,” which is correct. You can build your career around that. Again, the challenge with that is that you have to make sure that you are in an industry that is big enough and future-proof enough. You are going to have to keep evolving yourself every few years to do that.

Again, that said, you want to focus on that very specific niche, speciality area. I think from an overall sales career standpoint, if you want to focus on the technologies, I would say people process technology.

How do you manage the people? How do you coach them? How do you train them? What do you look forward to the skills that are going to make them good? How are you going to ensure that sales funnel flows through? How can you execute better than everybody else? What technologies are going to support you in doing that, and are they evolving where they need to?

I think it is a really hard one because I think there is an intervention as well today, taking millennial culture into play on this. I think it is super difficult because millennial culture flips between the two as well. You can come across millennials who are super money-driven, the same as it ever was; and yet millennials where money is not motivating factor anymore, they want to feel mission. They want to see the success of the company. You take that even further when you look at startups, I have been working with a lot of salespeople recently, who are not salespeople, they are startup people. They do not actually view their future in sales at all. The problem is that all companies need sales. They end up having to make sales anyway.


Jamie: Is that a reason why a lot of startups fail?

Avi: I think a reason why a lot of startups have failed to get traction is because they have not understood the nuance between selling to an investor and selling to a customer.


Jamie: Do you need both? 

Avi: As a founder, you need both, because ultimately, when you are selling to an investor, you are still selling, but it is more of a marriage. They look into different things than customers.


Jamie: If you had your sales career again, what would you do differently?

Avi: Great question. I think there are three big differences for me. Number one would be to seek out and maintain mentors at every stage. It is easier said than done. The second one is, I would always try and focus on the biggest market, which is a difficult one to do because, in life, there are always those questions of “Do I take the path of least resistance?” I had a very specific inflexion point in my career where there was the option between taking the US market and the European market. I picked the European market because it was easier, closer, but it was probably a mistake.

You want to focus on the biggest possible market there is. I think the third one is, salespeople are not generally shy. Advertise your success. I think the third one is probably the biggest mistake in my career, the maintenance.

Everyone knows they are supposed to be doing maintenance with your customers, and with your former employer. Those ongoing relationships that you build; you need to maintain them. I think you always need to remember that you need to maintain relationships.


Jamie: You mentioned ‘’, what other sales enablement technologies are you aware of that you think have the potential to really change the game? 

Avi: I think Gong is definitely one of them. I am seeing a huge explosion in startups in the sales enablement and sales technology space; including everything from AI to analysing and training against fake leads rather than real leads. A lot of these companies are in very early stages, companies that are trying to fix that element of the sales funnel all the way through sales enablement that is going to help you demo by listening to your demo and then inserting the relevant points: competitor, objection, handling, and things like that. They are in essence adding that AI element into the human interaction.

If you are in an F-16 fighter pilot jet, you have ‘pilot vision’ where all the data is being thrown at you in real-time, and technology is starting to add that to the sales process.

The biggest technology place that I have seen is when you have a good CRM, well-enabled. When I was a sales executive, I hated CRM, and I worked for a company that owned two of them. It was annoying, but when they were well-deployed, and they actually helped lead you and guide you in that sales process. If you have done it in the right way, the technology should not be a hindrance. It should actually be an enabler. Even the basics, like Salesforce, can be like that if the implementation is done well.






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