PODCAST 165: How to Transition into Tech Sales from a Non-SAAS Background with Lee Berkman

In today’s episode, we’ve got Lee Berkman. Lee’s an enterprise account executive at CloudShare, the world’s easiest-to-use virtual labs for software training, sales demos, and POCs. Lee talks about his journey on how he got into tech sales without having a SAAS background and learning how to sell by not being a salesperson.

If you missed episode 164 check it out here: Freelancer to Founder: Sales Lessons from the Journey with Kyle Racki

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Show Agenda and Timestamps

  1. Show Introduction [00:10]
  2. Cloudshare’s Purpose [2:10]
  3. Responsibilities at Cloudshare & Specific Use-Cases [4:44]
  4. Lee’s Professional Background [8:51]
  5. People Buy from People [16:43]
  6. Salesperson to Customer Success Manager [20:05]
  7. Life Is Easy [24:59]
  8. Paying It Forward [27:11]
  9. Sam’s Corner [31:52]

Show Introduction [00:10]

Sam Jacobs: Hey everybody it’s Sam Jacobs. Welcome to the Sales Hacker podcast. Today on the show we’ve got Lee Berkman. He’s an enterprise account executive at Cloudshare. He’s had a really interesting life doing all kinds of things from being a barman at an English pub in London, to selling door to door in Cape Town, South Africa; and now doing enterprise sales for Cloudshare virtualization software out of Tel Aviv. So it’s a great conversation. Before we get there, we want to talk to and thank our sponsors.

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Without further ado, let’s listen to my conversation with Lee Berkman.

Cloudshare’s Purpose [2:10]

Sam Jacobs: Hey Everybody, it’s Sam Jacobs. Welcome to the Sales Hacker podcast. Today on the show, we’ve got Lee Berkman. Lee is an enterprise account executive at Cloudshare where he is responsible for helping prospects and customers from startups and large enterprise organizations drive higher customer acquisition and retention by leveraging Cloudshare’s business acceleration platform to provide engaging hands-on software experiences, such as virtual training and remote demos and POCs anywhere in the world at anytime. Lee brings a rich set of interpersonal skills and technical knowledge having held a variety of international customer-facing positions in both consumer and high tech organizations. He grew up in South Africa, has lived in London and the US, and is currently living in Tel Aviv, Israel. Lee, welcome to the show.

Lee Berkman: Thanks very much for having me.

Sam Jacobs: So you’re an enterprise account executive at Cloudshare. We like to start with your baseball card, which really means just giving an opportunity to tell us a little bit more about Cloudshare.

Lee Berkman: I think in a nutshell, Cloudshare provides virtual IT software environments and experiences for end-users. What we do is we help enable businesses and companies to deliver an IT solution to an end-user, whether that be a user for training, for a sale, a development person basically doing product rollouts, testing QA, or the topic we’ll be focusing on today: sales. So you’re able to enable your sales engineers to have a catalog of ready-to-deploy demo ready environments over and above the actual, fully functioning software with added assets, materials, guides; and also provide an end-user, potential buyer, or a business prospect—proof of concept, proof of value, and a hands-on experience versus a very controlled mechanic. So, leveraging virtualization, easily delivered over a web browser, no software needed on anyone’s part; and that’s what Cloudshare does. We deliver virtual experiences, we deliver hands-on experiences.

Responsibilities at CloudShare & Specific Use-Cases [4:44]

Sam Jacobs: How long have you been at the company? Tell us how old is the company? How many employees are there?

Lee Berkman: So the company has gone through one or two changes in its life. It’s about a 14-year-old organization. I’ve been fortunate to be with the company over four years. My role, as you mentioned, I’m an enterprise account manager. So I’m responsible for working with new business prospects on adopting, evaluating Cloudshare. We’re past the 50 employee point now. So we’re kind of an incredibly mature startup in that sense. We have an incredibly well-polished and developed product and platform. We’re one of the industry leaders with regards to providing these type of experiences with the amount of insights and analytics, but still incredibly nimble.

Sam Jacobs: When you describe sort of virtualization and delivery, it sounds like it’s almost a horizontal tool that can be used in so many different use cases. Is that accurate? And if so, is it hard to describe and focus on the solution that can be used in so many different ways towards a specific use case? In this case, sales? Or is it a very natural use case? And everybody immediately understands what you’re talking about?

Lee Berkman: That’s a great question. And depending on the day you ask me, I’ll probably answer a different way each time. I come from a background of selling multi plugs, LED lighting, and basically home entertainment systems. So moving into high tech and learning what virtualization was, I’m still a geek but it was still a learning curve for me. So we’re providing solutions to parts of businesses that don’t necessarily have the IT know-how to grasp virtualization and being able to easily replicate IT solutions easily. And that makes sense; a salesperson doesn’t necessarily want to be able to set up an IT infrastructure so that their prospect be hands-on with it. But when you start being able to show and demonstrate how, with a little bit of preparation, saving an environment that can give them that hands-on experience, in a matter of minutes and a few clicks, the conversation becomes quite simple. So it really depends on who we’re talking to. We have buyers part of the IT department within an organization: that conversation is far more technical focused because they want to get into the nitty-gritty about how many layers are you able to support with customized networking? It’s a very different conversation to a salesperson: how am I able to showcase my solution and have insights into how engaged the prospect was? Two very different focuses, but end results are really similar and the platform provides all of it in one clean offering.

Lee’s Professional Background [8:51]

Sam Jacobs: That makes a lot of sense. You mentioned you’ve been at Cloudshare for years. I read in your bio that you grew up in South Africa, you’ve lived in London and the US. So essentially all over the world and then came to Tel Aviv. So walk us through a little bit of your story. Give us a little bit of the life story of Lee Berkman.

Lee Berkman: The life story is good fortune and lucky breaks. And, I guess, taking advantage of it nonstop. I grew up in Cape Town, South Africa; one of the most gorgeous cities you’ll ever be able to visit in your lifetime. Straight out of high school, I went traveling, I did not go to university. I went straight into working as a water ski instructor, a bar man in London, and getting my opportunity to be abroad. I came back to South Africa with not an exact goal or direction and landed up in sales. I actually landed up in a call center first and the sales director knocked on the door after a year of basically managing this call center; and he said: Lee, you’re gonna have to buy a suit. You’re gonna have to stop wearing colorful socks and you’re gonna come on the road selling with me. I still wear colorful socks to this day, by the way,

Sam Jacobs: I think colorful socks are a good conversation starter. I don’t think you have anything to be ashamed of.

Lee Berkman: Oh, no, no, very proud of it. And that’s how my sales started. I was six years for a wholesaler. So, quite different to what I do now, but still b2b; but I never worked in an office. I didn’t work behind a desk. I was in my car all the time. That was my office.

Sam Jacobs: And you were selling stereo equipment?

Lee Berkman: Like TV brackets, HDMI cables, speaker cable.

Sam Jacobs: And you were selling to retailers? You were selling to television stations, or offices, or just anybody?

Lee Berkman: I was selling to so many different businesses, we were selling to mom and pop shops, were selling to convenience stores, we were selling to large national nationwide franchises.

Sam Jacobs: And this is all across South Africa?

Lee Berkman: No, the longest journeys I did were like eight-hour drives to go see clients. And that was for five, six years. And it was a wonderful experience. I loved it. You build these incredible interpersonal relationships with human beings and you learn how to be a salesperson; you learn how not to be a salesperson, you make some incredible mistakes. And after a while, I was looking for a change and a fresh start. So what better way than to say I’m taking a sabbatical? Israel was my first stop. It was meant to be for five months, six months on a little holiday. And I’m on the same holiday seven years later.

Sam Jacobs: And how is it? How do you like living in Israel?

Lee Berkman: I’m very passionate about the country. I love it. It’s incredibly unique and a fortune of opportunity. They call it the startup nation, and that’s as true as can be. And I’ve had more work business opportunities here than I think I could have ever had back where I come from, and potentially in the UK or the states. English speakers fall into high tech pretty naturally. So I kind of started, I don’t say square one, but I was a junior.

Sam Jacobs: How do you start as a sales development representative? You know, trying to get meetings for other account executives?

Lee Berkman: So the first job I got had nothing to do with high tech. It was a company that did preparations for organizations that went to conferences and had to build like these big lavish stands and marketing materials and stuff. It was the shortest career choice I ever had. I went to the boss and said: Listen, this is not working for me. It’s not working for you. But let’s shake hands and say goodbye. Then my next job, I got was actually at a pretty well-known technology company called WalkMe. They’re looking for a sales development manager. Are you interested in the role? My immediate answer is yes, no problem. Speak to the recruiter. But when she mentioned to me, it was US hours, I was like: oh, maybe you have something UK hours. And they’re like, we have a CSM position. But I didn’t know what a CSM was. So I said, sure, that sounds like a good job to me. And I became a customer success manager actually, which was very fortunate because I got the wonderful foundation of understanding the sort of pre and post-sales of SAS sales cycles and acquiring a client, and then how important it is to nurture and enable them to keep them as a client. So that was my first position. And then exactly as you said, I became an SDR and then had the fortune of meeting Cloudshare.

People Buy from People [16:43]

Sam Jacobs: What was your experience in terms of the things that were surprising to you in terms of the sales motion, the sales tactics, and techniques? And what were the things that were really the same as what you’d experienced in South Africa, and really weren’t as different as people might think they are.

Lee Berkman: I guess what’s not different is you’re selling to a person, you’re dealing with a person at the end of the day, I remember when I first became a sales rep. My question to my manager was, why are there sales reps? And I didn’t mean it in a funny, facetious way, I meant, there’s so many options, there’s internet available. Someone looking for a product, going through the phonebook, looking online, getting a price and ordering it. It’s like, why do you need salespeople? And I think the old truth is people buy from people. And I still believe that to this day. And SAS is an incredibly competitive space because of how smart buyers are, how much information is out there. But at the end of the day, somebody is going to be committing to a solution, but they’re also committing to their provider, they’re committing to somebody that’s going to support them throughout their adoption, their process, with SAS sales. So that’s the same, whether I’m selling you a multiplug, or whether I’m selling you an annual subscription to help support you and your 200 sales engineer delivered demos of your software solution. That’s the same. And I’m shocked at how people think it might be different because it’s not. So that was something that surprised me. And people still maybe don’t always see it. But some of the big things that are different is not seeing humans face to face. And, you know, I’m sure COVID has changed so many opinions and ways that people can sell and do so and just engage. Before COVID, I didn’t have my webcam on every call. Now I do. So yeah, there are so many of these running parallels that are exactly the same to me. People buy from people, even if it is through a little computer screen now, or whether it’s sitting face to face.

Salesperson to Customer Success Manager [20:05]

Sam Jacobs: To your point, one thing I think is interesting in the SAS model that is still debated, which is to your point about: people buy from people. There’s this experience where the salesperson tells you something, you’ve spent a long time building that relationship exactly to your point, you think that you’re buying from XYZ salesperson, you then get transferred over to a customer success manager. And the customer success manager is a different person and a different relationship. And it’s just different. Sometimes it’s better, sometimes it’s worse. But it is a break in the relationship between the first person that you experience who represents the company, the brand, and the value proposition. And then the next person who extensively, theoretically, represents the same things, but may approach it from a different perspective. Do you as somebody that has built all of these relationships, you know, through door-to-door sales and hand-to-hand sales; did that not make sense to you? Sometimes people are surprised or confused at the existence of a customer success team. And they say why doesn’t the sales team do that too?

Lee Brinkman: Very much so. My first role in high tech, as I mentioned, was a CSM, which is something that I love because you’re basically getting them to enjoy what you’re offering them. However, the salesperson still kept tabs; I noticed that from WalkMe days, and you’re 100%, right. It’s common practice that that is the case. And often, the person that goes to the sales journey, the evaluation, the actual procurement, budget approvals, and purchasing culture is not the person that’s going to be using closure moving forward. They get put onto a project team. So you know, the relationship almost changes dynamic; and who you’re dealing with, from the client side. One of the things that I love about CloudShare is the fact that we differentiate ourselves a lot of the time is the fact that we position ourselves so much. So again, I think it’s one of the things that really spoke to me about the company and why I love dealing with our CFO or CEO, and all the VPs, actually, all the C-level leaders of my company, is we are so invested in our clients. We take so much more time to understand the business need, align what their goals are. And clearly, we see the benefits of the culture. Our retention rate of our clients is really high. We have clients that have been with us for eight years, nine years, which is pretty great going. So the fact that clients are invested in Cloudshare, because the platform does so well, but because the support and the relationship is really valued.

Life is Easy [24:59]

Sam Jacobs: We are almost at the end of our time together, but one of the things that you sort of said in the past that I think is interesting. We asked the question: what’s something you believe that others don’t? And your response was, life is easy. When you say that, tell me what you mean, how do you approach it? How does that relate to your philosophy? I’m just personally curious.

Lee Berkman: So life’s easy is a silly thing to say. Because it’s not the truth. And things that matter will often be the most challenging. I was a dyslexic kid. I wasn’t good at school. I wasn’t sporty. I wasn’t like the most popular kid at school. I wasn’t the most hated kid at school. But I didn’t have a clear path. And people weren’t sure that I was going to be able to be independent or achieve anything. But the truth is, I got to do whatever the hell I wanted. I wanted to go traveling after high school, I did that. I wanted to be a water ski instructor at a summer camp, I did that. I wanted to work pubs in the UK, I did that. I wanted to be able to make enough money to pay my way, I did that. I managed to move to Israel. When I got here, I decided this looks like a good option and I did that. And I’ve heard so many people tell me that won’t work out, don’t do that. You can’t do that. I’ll get it done. So when people say, it’s not possible, I can’t do it. I’m saying I could do it. No one told me, you need to be a salesperson; I landed up in sales. So life’s easy. Not life’s not easy this week in Israel. But if you want to get something done, you do it at the end of the day. So I like to think life’s easy. I think if you fake it long enough, that might be true.

Paying It Forward [27:11]

Sam Jacobs: I understand. And I appreciate the perspective. And there’s a lot of stoicism in that perspective. So whatever life throws at you, you can take it and you do it with a smile on your face. Lee, we’re roughly at the end of our time together. And this is the part where we like to pay it forward a little bit and figure out: are there people in your life? Are there ideas in your life or other books in your life, it can be anything you want? But we’re trying to follow the breadcrumb trail, we want to know your influences and give us one or two people or ideas or books or pieces of content that you think we should know about that have been important to you.

Lee Berkman: I was lucky enough to watch my dad and maybe a core detail I left out was the fact that I got that job initially, after my years of traveling, was the fact that it was my dad’s shop. And my dad grew up not being given anything. And he had to work hard because he had no other option. You know, he borrowed money from friends and didn’t have a dad look after him the way I had. So when I ended up working with him, I got to see a guy who was incredibly determined to make sure he made success, because he had no other options. So that you know, that was always a motivating factor from the guy who never took a sick day. So I got to look up to a guy who was a hard worker, but also a boss and a leader. As for books, on a completely different tone, was Jack Kerouac’s Dharma bums. Amazing journey, amazing stories about his life on the road. But there’s so many things; the truth is I love TV shows, not just because I love sitting in front of the TV, but I love how much effort and I think production value goes into these things.

Sam Jacobs: If folks are listening and they want to get in touch with you. Maybe they want to talk about Jack Kerouac, maybe they want to learn about Cloudshare. Is that okay? And what’s the best way to get in touch with you?

Lee Berkman: Oh, absolutely. So LinkedIn, Lee Berkman is always an easy one. But being on the customer-facing team, I’ve got a pretty easy email address as well, it’s Lee@cloudshare.com. I’m always interested as well, just to hear opinions, for any of your listeners that are actually taking advantage of virtual labs, whether that be in-house, a lot of companies will manage it themselves. I’d love to learn more about how you’re doing and why you choose to do it in-house. And if you’re potentially interested in learning more about how Cloudshare can support your business, help a specific project you have, you’re running a user event in the coming months and you want to be able to have hands-on workshops for 1000 delegates or 2000 delegates, get in touch. There’s a lot we can do.

Sam Jacobs: Sounds great. Lee, thanks so much for being our guest on the show this week. We’ll talk to you on Friday for Friday Fundamentals.

Lee Berkman: Such a pleasure. Thank you very much for having me.

Sam’s Corner [31:52]

Sam Jacobs: Hey, everybody, Sam’s corner, Sam Jacobs. Great conversation with Lee Berkman; really interesting guy and took away a couple of great sort of ideas, insights from that conversation. But the first is that, you know, there’s a lot of people that are trying to make a transition from other kinds of sales or other kinds of backgrounds into tech sales. And there’s a lot of recruiters, a lot of hiring managers that say, you really really need a SAAS sales background in order to be effective in dealing with customers. And I think Lee is a testament to the fact that no, you don’t. I think if you’re out there listening, you’re in HR, you’re in recruiting. And you think that people need five years of SAAS sales experience, because that is definitional, what makes a good salesperson or the only thing that enables you to sell SAAS, that’s not true, you’re wrong.

A lot of different kinds of people can sell. I was just reading on LinkedIn that some of the best salespeople all came from being bartenders. Any kind of background can be successful in sales because sales requires training. If you train your team, and you empower them with the right tools and enablement, then really, it’s about their aptitude, their ability to have good conversations, their curiosity, their empathy. And that doesn’t require knowing the difference between an SDR and an account executive and a CSM. Those are all learnable things; if you can learn, then you can learn SAS sales. So if you’re out there, and you’re discriminating against people that are trying to get into SAS sales from other backgrounds, you’re doing the wrong thing, and you should stop it.

The other thing that Lee said is people are people. And again, that’s sort of the point. There’s this continued upside, which is he also said people buy from people in the absence of just features and websites. Buyers still want to have conversations and they still feel like they’re building a relationship with a specific human being. So remember that as you venture out into the world of sales. I thought it was a really good conversation. So thanks for listening.

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