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Ep. 53: Million Dollar Deal, Billion Dollar Outcomes with Rob DeSantis

77m 32s

Ep. 53: Million Dollar Deal, Billion Dollar Outcomes with Rob DeSantis

Rob DeSantis began his career as a mechanical engineer at Hughes Aircraft but sought to augment his income, leading him to sales through Herbalife and stock brokerage at Drexel Burnham. These early experiences taught him resilience against rejection and the critical skill of "ruthless qualification"—focusing only on high-potential prospects. He transitioned to selling engineering software, where his technical knowledge allowed him to excel, quickly surpassing his engineering salary. His success led to a role at RASNA Corporation, where he dramatically exceeded sales targets by implementing disciplined time management, such as prospecting early to reach engineers before meetings. DeSantis later moved to Germany to expand sales internationally, learning to navigate cultural differences. After RASNA's acquisition, he co-founded Ariba in 1996, recognizing an opportunity in internet-based procurement for indirect materials. Applying his proven sales tactics, including creating urgency and leveraging customer advisory councils, he closed key early deals with companies like AMD and Cisco. Notably, within five months, Ariba became cash-flow positive after closing several multi-million dollar contracts, marking the most significant deal of his career and establishing the company's foundation. His journey underscores the power of combining technical expertise with disciplined, customer-focused sales strategies.

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(upbeat music) - This is how the deal was done podcast where we interview top sellers and leaders on their biggest and most memorable deals. I'm excited and honored today to be here with Rob DeSantis. Why don't I pass it over to you Rob and set us up on your background and journey and we'll talk about some of your deals. - I think first of all, I'll say that there is one deal in my sales career that stands out amongst all the other deals that I've done. It was a deal that was done for a company that I co-founded called the Reba Technologies. It was done about 25 years ago. The deal was about $10 million in size and the sales cycle was about four and a half months. - So you started in Rhode Island where you went to college, what you did after college and how you maybe got into sales? - Well, I was born and raised in Rhode Island went to the University of Rhode Island. It was a mechanical engineer. And right out of school, I went to work in Southern California for Hughes Aircraft Company doing structural analysis on satellites. And I quickly realized that if I was going to have the life style that I wanted in Southern California, I was gonna need to figure out how to augment my salary as an engineer. I started looking, this is back in 1985. I started looking pre-internet at the Sunday times to figure out how to augment my salary. And I saw on ad that said, earn 10,000 a month part time. And I thought to myself, I can do that. If there are people who can earn 10,000 a month part time, I could be one of those people. So I started that process, I call them up, a company that had been an herbal life. - Okay. - Loose right now, ask me how was their slogan? And I spent about nine months learning every Thursday night going to a business organizational meeting and doing the things that they were teaching us to do and learning how to do a bunch of cold calls, how to handle rejection from all the people that didn't want us talking to them. And I did that. I then shortly after not making much progress on that, I a friend of mine said, hey Rob, the stock market's a hot place. Why should you go try, let's go try and sell stocks. So I got my series seven license. And I tried getting a job as a stock broker from one of the major firms. But this was the spring of 1987. I was 23 year old mechanical engineer working. I had no book as they call it. I had no network in Southern California. - Yeah. - So I could not get anyone to hire me until finally I got Drexel Burnham to bring me on as a cold call for their brokers. I convinced the branch manager that I would work harder and smarter than all the other people that he had. So what I would do, he told me, don't quit your day job because I don't think you're gonna make it, kid. But what I did was I'd get up every morning at 3.30 to 4 in the morning. I'd get to downtown LA by 5. I listened to the stock ticker recommendations between 5 and 5.30. Wall Street Journal read between 5.30 and 6. New brokers meeting from 6 to 6.30. And then the dollar goes off at 6.30 out in the West Coast because of 9.30 East Coast sign. - Yeah. - And we started dialing for dollars. And I started dialing for dollars from 6.30 to 7.30. Then I'd get in my car. I drive to Hughes Aircraft Company. I would do my engineering from 8 to 5. I'd get out, get in my car, drive back to downtown LA. And then I would call people at home at night from 6 o'clock to 10 o'clock at night and drive back and do it again the next day. - Were you the only one doing that? Or did you just feel like this was normal? Or you just said, hey, I need to make some extra money. What was it like in the moment? - I was so determined to figure out what my path was in life. And I was convinced it wasn't being an engineer in a large firm like Hughes Aircraft Company. But I wasn't quite sure, should I go back to law school, should I go and get my MBA? And people had told me because I have the gift of gab that I should try sales. - Yep. - So that's how that all started. So I tried doing those two things. And then in 1987, I did that for like six months. I was the only one that was working two jobs. Now the cold call was where a fresh house school living with their parents just trying these things. But I was doing this crazy thing. And October of '90s, then it came along. And that's when the stock market crashed. - Okay. - On that black Monday, I think they called it. Also the movie Wall Street came out. And I was like, and the key actor I came or was Charlie Sheen or or someone else. Said, yeah, I don't wanna call people at night at home anymore. And I thought to myself, I don't wanna call people at home at night anymore either. - Yeah, it's tough. So I was frustrated with the market crashing at calling people at home at night. And then one of the consultants, a huge aircraft company, said to me, Rob, with your knowledge of engineering software and your skills and structural analysis, why don't you try and sell engineering software? And at the time, I was so naive, I didn't even think they were jobs that they did engineering software sales. - Okay. - I thought software and hardware came together on one bundle. - Yeah. So that contractor set me up with, meeting with a small software company that the structural analysis based in Santa Monica. It was a USC professor who had, PhD students working on the software. And in 1988, I cut myself from the mothership of Hues. And that was a huge thing. I took on my job at structural research and analysis cooperation, taking a hundred percent commission job. - Okay. - I mean, you don't sell, you don't eat. And they agreed to lend me $1,000 a month for the first six months to give me a chance to get there. - Your feet under here? - Get my feet under me. So that was a big milestone that transitioned me. Pretty quick, I saw how they were selling and the people that were selling didn't have any technical background and were just dialing for dollars, but from ads that were coming to them from Mechanical Engineering Magazine. - Okay. - And I was like, wow, I could actually talk to the engineers. And from all of the ruthless qualifications I had learned from herbal life and from Drexel and the stockbroker world, I was delighted that these people actually wanted to hear from me. - Right. - So I was able to call them up, talk to them about their engineering problem, talk to them about how the software could handle it. I would even say 70-some information and I'll do some structural analysis for you. I'll show you how it works. Within six months, I started surpassing the income that I had made at Hughes. - Okay. - And within a year, I was making roughly about 10 times the amount of money that I was making as an engineer at Hughes, which really got exciting for me. I felt at that point, I reached a pinnacle of my career. I was a whopping 25 years old. I loved my job. I was doing engineering work every day. I was selling and I was quite content. Then I get a phone call. I get a phone call from a gentleman who I ended up working with for dozens of years, a gentleman by name Keith Crock, who was the head of sales and marketing of a 35-percent startup company in Silicon Valley. He called me up because they had become one of my customers. They noticed I was putting up monthly newsletters to my whole ecosystem, which they were part of. He was like, "God, we gotta hire this guy." Keith recruited me to come in and work at this company called RASN Corporation. There I spent five years. They first hired me as a sell on the West Coast. First on the East Coast and a person in the Midwest, and they would just have their first initial product out for sale when they hired me. We had our first meeting, the first week that I was there. They got the sales team, which were three of us, up a corporate and they said, "Okay, everyone tells us how many sales the community can make over the next quarter." I remember looking at them and everyone wrote down their number and the guys on the East Coast said, "Many one." Another one on the Midwest said, "Maybe one." And I said, "Oh, 20." So I thought roughly 20. So they were like, "Oh my God." They didn't believe me that I could do 20. Well, long story short, I have been doing 41 deals in my first 90 days of the company. They were flabbergasted that I was able to do such a thing. So they sent down a board member to ride shotgun with me for a week and just see what typical day and week-- - In the library. - In the library. So they did that and by the end of it, you went back up and reported that you should hire this guy, make this guy your head of sales and move him up north and let him build a sales organization. So they did that and that was another big mark of my life to actually leave my lifestyle and commission structure that I was used to go into sales management. Okay. You committed 20 deals. I don't know if that's it. that's New England, Northeast, arrogance, or just like, you know, we think that we can do stuff better than everyone, or maybe it was naivete, but you had, you committed 20, and then you did 40. That's crazy. How did that contribute to what you-- - Yeah, well, you know, I have to say, give credit to the path that I was on, with respect to that. First of all, I was raised, you know, if there's anything I wanted, I have to go work for. So my father was very tough. You want a car? Go work for it. You want this. You want new sneakers? Go work for it. So whatever it was there. So I didn't have-- I didn't mind the work mentality. But I would say that the thing that was really magical for me was all the training that I got at herbal life. I'd go out every night and put a thousand flies out at night in the mall, just to try and get three or four people to call me every night. And then I would go into grocery stores. I'd go into people's loose way. And I'd say, how would you like to lose way and be wealthy? And they would say, who is this weirdo? And they would call for help, but I'd be at-- run out of the grocery stores and stuff like that. So the story I like to say is, with herbal life, I had physical rejection. And then when I was at Drexel, I was a broker, I just had verbal rejection. Don't call me a night. In Drexel, they said, we're going to teach you how to make a thousand calls a day. And they started saying, look, the type of people that we're going to sell to are this type of type. And these type of people answer the phone a certain way. If they don't answer the phone that way, hang up. Don't waste your time. They'll say, but people will answer the phone in less than two rings. If they don't, after two rings, hang up. You have 30 seconds. It's a lot of them ready. You're calling to give them to the best $10,000. If that scares them, or gets them a fring, hang up. So they taught me ruthless qualification. Ruthless qualification. Don't waste your time talking to people or organizations that aren't going to spend the money. Get to the people that will. And I would say, in my career sales, the sales people that end up being the ones that they know had to sell the product, but they're unsuccessful is because they get too excited about anyone who's willing to listen to them as opposed to doing a ruthless qualification. So I did that ruthless qualification. So when I got in that new job, I was like, I got a little pipeline. I got to be ruthless qualification. And I did that. And I ended up hiring eight people pretty quickly. And I had them set up my duplicate, how I set up my office, and how I spent my time, time management, for example. Engineers typically find them in early because they like to go in early and leave early. And when I-- not early than they should, but they like to go in. Maybe work seven to four as opposed to eight to five. So I knew I could typically find them at their desks from seven o'clock in the morning until eight thirty before they started all the corporate meetings. So I would do all my prospecting from seven to eight thirty. Where the average sales person was showing-- 9 o'clock. 8, 8, 30, 9 o'clock. Have a cup of coffee, start their call calls, not get anyone because everyone's in their meetings. I was-- by 9 o'clock in the morning, I was-- I was-- in my follow, it means why I had scheduled calls. There you go. So I did that. And they brought me up North. And I ended up spending the next four and a half years there. The first three years are two and a half years. I was there. Post my movie up there. I built a sales organization throughout North America. Roughly about 60 to 80 people in sales and support and services. And what have you? An early like 93 or something like that. I was frustrated that I was given 90% of the-- Target-- of the target number for the company. Yeah. But only 50% of the budget. OK. And I was like, why is that? And they said, oh, Rob, you're too young. You don't understand doing business internationally. And they say it's much different and it's very expensive. So-- It's a great lifestyle, too. Yeah. I was like, well, I'm 27 years old. I'm single. I said, move me there. Challenge accepted? Yeah, challenge accepted. So they moved me there. They sent me to Germany, which I ended up being interested. I had an incredible experience in Germany. I had a girlfriend at the time. I made her a fiance. We got married before I went to Germany. So a new life, a new life excursion moved to Germany and spent the next year and a half there. In the first nine months that I was there, I was able to get the C, all the things that were similar and all the things that were different. OK. And as it turns out, there's not too many things that are different. I mean, there's some logistical stuff that's different. And there's language and there's some cultural stuff. But at the end of the day, sales of sales, value, is value. If you can communicate that, that was great. What I also learned, though, at the time, was we had a German gezefster fear, who was the head of our Europriorge at me going out there. And so you had a German trying to sell to England, people at the companies in England, in France, and all the other places. And the cultural differences did not blend well. And also what I found was being an American, I was like neutral. I was like Switzerland, that. So I made it easy for me to create an organization throughout the continent, throughout Europe, and build in a direct sales organization and resell was where appropriate, in some of the more third world countries. But I was having a lot of fun doing that. I was planning on being there for three years when the company got bought up by a Boston-based company called Paramount Technology. And from there, I came back to Silicon Valley. I had made a little bit of money with my stock. But I came back and decided to take six months off and figure out what I would do next. And doing that, it was great. I got some great advice. One mentor of mine had said to me, I was taking two months-- I had taken two months off a raid. I was getting itchy to go. Goes back to work. I had no idea what would you need to want, because I loved the company I was with so far. And he said, Rob, go take off three more months. They said if you go for it, you will think totally different. I think outside the box. So I did. And I then started-- now this is 1995, in early 1996, late '95, early '96. And the internet was hot. Yahoo! Just going public. Netscape was public. And I was amazed by this new paradigm shift that the internet was causing. And so me and a couple of the salespeople lived close by that I had developed a friendship and a relationship with. We'd go to some of these conferences that were being held on this new thing called the internet. And one of them was a guy by the name of Paul Tao. And Paul had been one of my sales reps. And he came up with the original idea for a reba. OK. And he said to me, one day, I remember March '96, he says, Rob, when you see we started a company, they said, doing what? He says, when we got purchased orders, how did we get them? I said, of course, well, we got them in hard copies or faxes. And he's like, yeah, this whole internet thing. There's just a thing we're getting differently. I said, I'll big companies. Those big companies, they'll do it. And Oracle or SAP. And he says, well, yes. But they're so focused on trying to move their financials and their direct material supply chain software to Java and to the internet from the old C++ and 4TRAN code. They sell-- there's a blind spot that they're not paying any attention to. I'm like, really, what's that? And he's like, indirect materials. So companies buy-- essentially, two things. Direct materials and indirect. Direct materials are things that go into the cost of goods sold and indirect are the things that you buy to run the company from furniture to office supplies to IT equipment and you name it. So call the company EQuest to be a play on request, except-- and we wouldn't have presented-- we had a company and we pitched it to four or five companies. And they all-- we used some curiosity to ask what the value would be. We learned through a consultant, Barry Ryan, about who writes, of course, the selling through curiosity, how to shorten the sales cycle, increase the size of the order and create better predictability by using curiosity and in an amazing way. So there were five magic questions we learned to ask. We asked those five magic questions and said, oh my gosh, we have a company here. So Keith Krokko would recruit me at RASA. He was sitting as an EIR over at benchmark capital, along with Paul Hagerty. He had been the CTO of EPV engineering for next computers with Steve Jobs. They were there. And we wouldn't talk to Keith about starting the company. Our old control at RASA as well, he was interested. And we met a couple of people. other people that were on the south side trying to start their company by creating supplier account logs. And the seven of us got together and we co-founded Ariba in 1996 and officially in October of 1996. And there I ran sales and I did the first few deals along with one of the gentleman, John Magna, who was one of my other sales guys that I brought with me from Razzna. And we did the first four deals, Octo, AMD, Cisco, and Visa. And I remember, Octo was the first one that we negotiated and we called it the Confusion Close because we got, it turned into like seven o'clock at night. I just kept working with the purchasing director and John said I kept circling my pencil around different things but we called it the Confusion Close Wear. And eventually all got so confused from talking so long that we just closed the deal. And we got the deal closed and we went out in the parking lot and we jumped up in the air and hugged each other because I knew at that point, I mean it was a, it was a, you know, $600,000 deal and I knew that that was the beginning of something great. And but that wasn't the, that was the material deal but it wasn't the biggest deal I had done. And when we did our first two deals, you know, we had created a playbook of how we sold, how to create urgency and scarcity. And we did this by creating customer advisory councils. And we had a special secrecy of what the agenda of those councils would like. And then we created a sense of urgency and scarcity with all the prospects that were about 45 prospects we were working with four months into the company. And on March 21st, 1997, company was officially five months old. We, yeah, about, we were about five months old. We closed four deals, rock, television, one of them, but for roughly about two point, it's four million dollars. And at that point, the cover was cash flow positive and profitable. We started building the sales organization, building the company app and using those assets. And then in 19, and then a year later in April of 98, I closed four more deals with the three other sales reps that I was working with. I had hired, I was working, but I was working those deals intimately. And we closed four deals for roughly about 8.6 million. And that was a big watermark. So at that point, we now were, had been operating plan and we had the ability, we knew that ultimate goal was to be a company that we said was built to last. We wanted to take this company public. Since our customers were global customers, we knew this time to go international. And we had some cultural elements about, you know, hire people better than yourself. Check your egos at the door. No ideas, a dumb idea, no ideas, a facetios. And by this time I built North America to be about Haiti people. And the next frontier was Europe. So I said to the CEO, I said, "Keep, let's go hire." The VP of sales from SAP or someplace like that to run North America. And then you're going to scale it and I'm off to Europe. You're out of trip part two. What I had done roughly a month prior is to, I wanted to go in there with some momentum. So I, we, Helipack was a partner at the time. Some of the big consulting firms were all partners. So I had talked to the different country managers so I could go do a tour through Europe and have them invite different prospects in. So I could expose that this incredible technology that Riba was canvassing the United States with. And they got a few prospects in each country. And so I had made an initial contact in September of 98 with Phillips at a Helipackage. A sponsor seminar, if you will. And I had been, I had developed a budget of $3 million. I was going to spend $3 million in my first year at a Riba. And my goal that I was given by, by, keep the CEO was Rob, go, go, produce $3 million worth of revenue. Okay. So that you're not a drain, I cash and you're not a drain on profitability. So I said, great, $3 million expenses, $3 million in revenue. I need to beat that number because I want to be a profit contributor. And I had to go build an organization. So that calls me to build an organization of maybe roughly 10 to 12 people at the time. Over the course of the year. So I got there, I had to buy my time into selling, into building Europe and into communicating A back to the things that were happening, the things that were seeing back at the home office in Silicon Valley. So what I would do, it was a, it was a crazy time in that year that I was there. I would, from eight o'clock in the morning till four in the clock at night, typically at four o'clock in the afternoon, I pretty much was selling. I kind of did the exact same thing when I started at a Riba, when I started search for research, I was calling prospecting, talking to all the potential partners creating an ecosystem, creating major events for us to have impending events to try and create some urgency and scarcity around that stuff. And then I was interviewing at dinners and nights and weekends. I was interviewing candidates in all the different countries. I was traveling four days a week to different countries, a different country every week. So I was doing all sorts of that stuff. And then pretty quick in my first, in my first month, I had a follow-up call with Philips, Philips, the big electronics from the make television sets, the lighting, the huge, the first thing I was selling to was very, very similar to my father. Okay. So I thought and how he acted and I took my life with my father. So I knew how to sell to that and I knew how to build a relationship with that. The first thing I did is I went in there and I asked the five magic questions based on those magic questions, based on his answers. I then set up, I then tried to call if I'd understand the decision-making process. I challenged him that he didn't have the horsepower to make the decisions. I created some urgency and some scarcity saying, "Hey, there's only one of me and there's all of Europe." So I got to figure out who I'm going to spend my time with this first year. And so I was able to do that. What are the five magic questions? So the five magic questions, credit goes to Barry Ryan, Sound Through Curiosity is you go in and you ask the customer the current situation. I like the dislikes, the ideal solution and what's the value that comes to you with that. So I'll give you an example. Let's pretend it's a reba. I'd go into you and say, "You are Phillips." Yeah. As John was saying, "Hey Dave, how do you currently buy stuff?" "In direct material stuff here at Phillips." It's messy. And he would say, "Oh, it's messy." And great, lots of routing, approval, lots of paper, lots of all this stuff going. And while he's doing that, I learned how to take notes. So I'm taking notes and I'm doing it in front of Dave. So I'm writing notes on a easel, on a white easel. And I'm writing down all things saying, "It's messy. It takes a long time." And users don't like it. But it's just like, "Well, what do you like about this?" It's a control, you know, or CFO wants to make sure things don't accidentally get bought. I'm like, "Okay, great. So control, anything else to like about it?" No, even as purchasing, we don't like it. So I was like, "Okay." I said, "What do you dislike about this?" Well, the end user takes them typically about three or four months for us to get in order processed by the time they start to time it finishes. Sometimes they don't even need the stuff after four months later. So he says, "I could tell you so many things, but it's just ugly and mess." So I said, "Got it. Okay. So let's recap. Here's how you currently do it. Here's what you like. Here's what you do dislike. Okay, I got that. And I would draw a line between each question. So it gave me time to go, "A place on my paper to go layer and ask more questions should I so choose." I then said, "Okay, question number four was, all right, I hear what you like and dislike. If you could wave a magic wand and have the ideal solution." What would be some of the attributes about that IJL solution? So he would say, "Well, the IJL solution would take advantage of the Internet." The IJL solution would allow users to select the things that they want automatically, like a shopping cart like this Internet thing offers, but you would have all preferred prices in there. And it would show first the end users who are preferred suppliers where so they could look their first but if they couldn't it would still allow them to go out and look from other supplies. So they could see and once they fill up their basket and they said let's go The HR our HR system would know who their manager was and who the chain of command was and it would route it would route via email the the order for approval and once that could done Then it would go to purchasing and if it was a pre approved supplier and a pre approved amount The order would go directly to the supplier and purchasing doesn't even touch it and the customer could get the the delivery in about a week and He goes that'll be unbelievable So I would say great now what would the value that be if you had that if you had that ideal solution You don't really understand Robert if we had that type of solution We have 300 office suppliers around the world that we do business with And everyone just goes off to their local supplier office supplier and they pay list price He says we buy about 40 million dollars worth of office supplies alone If we were able to funnel that To BT here in Europe and office depot and staples in the US and just two of fuse fires We could easily get a temperature discount a 10% discount will be four million dollars And we could do the same thing with IT we could do the same thing with furniture We could do the same thing with this commodity that commodity He goes this solution if we had a solution like that we could save easily a hundred million dollars directly to earnings per share Wow I'd say great and I'd be writing that down And then what I did and looked at my easel I said okay, so I'm going to say here's a current situation His likes decides here's what the ideal solution would be and here's the value you get out of it You're damn right. I go this is a reba With a clean sheet of paper Two years ago two and a half years ago We went off and talked to 32 corporations in the first 30 days of our company's life And did exactly what I just did here with you Asked the same questions They told us the attributes of the ideal solution and guess what Dave Is an 85% overlap of what those ideal solutions we have so we took that list of idiosolutions We created a list of requests we brought in all those 30 decorations We had them prioritize Because we couldn't build these 200 features day one We had to prioritize which was for release one release two release three And we would now build the product we were designed by the people priced by the people And deliver to the people wow So was that customer development the learning upfront that allowed you to have that conversation with the global buyer procurement from Phillips and he told you about all of his issues and you said voila So yes, and so what happens is is I was able to connect with him at a very personal level I was able to align what his thoughts and visions were with those of many other corporations I was able to really let him understand that I really understood his problem And the opportunity that was there And so Once we did that we were connected yep the relationship and been developed trust and the trust and so says so I said but next time Look let me let me Bring out the product will show you the product time. If that let me bring it bring in Greg my guy came with me from the United States And I haven't talked to you he was a professional service guide for us back in you guys he'll talk to you about how we implement Let us show you how you customize it Let's talk a little bit about what the decision-making process is And before we spend too much time together You know, I'm gonna need to understand who's gonna sign who's gonna make the decisions? Who's gonna sign the checks? What that process is gonna be and if I feel like we can make this decision in a relatively fast time frame Then you know what they've I'll see you every week. I'll do whatever takes but if the time frame that it's gonna take Is gonna be elongated. It's okay. I'll make your customer next year or the year after but I have to focus my intentions On people that want to have this impact today. Yeah, so I say if you want to have this impact and we point you in at the At the whiteboard if you would have this impact today Then let's do it urgency and scarcity You brought it in with the curiosity made it his idea and then brought his idea alive. Yeah And we ended up Doing that deal now. I want to tell you a little fun thing about this. Okay, cuz sales people love competition. Yep So remember I told you we brought in ahead of sales uh You know six months before I head off to Europe. Okay, so we had some overlap time a great guy and And he in the fall of 98 Well, I was working this Phil's steel Was working hard I was gonna aggressive on on a deal at he'll pack or to deal at Chevron with the sales team that I had brought on and and January They closed both of those deals both those deals were multi-million dollar deals you know, I'll say bigger than four but less than nine And the company was so excited when they did those deals that the CEO Keith oriented and the CFO ordered some crystal trophies to get the sales team and the entire set of team that worked on Cluck getting those deals closed and those sales like that had been like 18 months. I was working those deals before they come before you left before I left So those are 18 months sales cycle thought on on those on those deals And they were gonna have a Friday afternoon Company wide meeting Bring the sales team up present them with that Well, that that was the second week in February what that was gonna happen I was working my deal of Phillips very in a stealth way I was working it I was uh Handling the resources because we were in Europe is me and I brought two people with me so we were working it I was doing the customer references calls and it uh from the US because I had relationships with a lot of the customers They were mine. I got our CFO involved and make sure he answered that the software license agreement issues But he can't sign them the secrecy he did And on the night before the big company meeting where they were gonna give awards to the number one sales guy And the VP of sales in North America and everything I closed 9.8 million dollar deal net 30 days clean deal uh And I I was so stressed out about it wanted to get it in on time that I remember I got caught this terrible cold But I had a faxed to me 27 page software license agreement and the Sales order and the purchase order everything I then faxed it into this first sales guy at a river john magner I said john I told him about the deal. He's like oh my god drop. This is gonna be unbelievable I said yes, so john tomorrow when they getting ready at the company meeting to present To everything to the people who did those small ideals I said I was your run up on stage and say wait wait wait Rob just brought in a 10 million dollar deal from Europe And so sure enough they did that and uh and uh it was so uh competitively sweet yeah uh and uh and a good positive way for me to do that and uh so that deal And it would be in so instrumental to the company uh and so uh personally exciting for me Um that it stands out as well What happened to the company after that deal? Well the big thing that happened at companies we went public uh what happened was is this is February of 1999 We knew we needed to build a backlog to go public so that we wouldn't miss numbers. Yep and and by the North America hit getting their petudials They had kind of gotten us to a point where we were tracking to be on plan or slightly ahead of plan Which was great Uh but my deal Put us away over plan i was supposed to do three million for the year I just did 10 million in my first four months ended up doing about 17 million that year But but we did we did uh but with that that gave Keith the CEO and the board Uh the confidence to pull the trigger to select investment bankers and then we'll public in 1999 and in June of 1999 we were IPO of the year uh and uh uh for For Wall Street and uh and the company Became the the Wall Street darling rocket ship that that that it was Wow, so how the deal was done led to the the company going public and it's still around today Yeah, and there's some incredible experiences I had with it read that I mean we were from zero To 250 million in revenue four years, but a lot of people don't realize we went from we went from time with one public We went public in a three and a half year we went public a three and a half when we were three and a half years old And we have 341 employees and all three hundred and forty one employees had made a significant amount of money in that in that in the Middle East. And then even the receptionist and all the assistants that were fantastic, we then went from 341 people to 3,000 people over the next year. Wow, or 2800 people. Yeah, I mean, tremendous growth and a very exciting time. What was we in Pupil? We became in the corporate world household name and lots of people wanted to have business with us. One of the most exciting times was I was on the phone, trying to do a deal with a very prominent computer PC based company. And I had one of the richest people in the world on the phone from their very successful software company, talking to the CEO, a founder of their company, telling them why they needed to buy a Reba. And I'm like, I could not believe I had these titans of the technology market on the phone selling on your back. My product, or the other. I got, when we finished that call, I called my mother and I said, you know, I could believe a call, I just had these. It was kind of fun. So it was a great time. A Reba had a great culture in those first three and a half four years and it was fantastic. Wow, we haven't stopped there. So we'll take a quick break and then talk about what you've been up to since a Reba. The big deal with Phillips, the company went public, shot up to a $40 billion market cap, and what's been going on ever since then? Well, you know, I'd love to rebuke. I believe a Reba Red. I think I always will, but you know, I woke up one day, year 2000, and I woke up one day, and I was traveling. I could say, but I always say I was traveling eight days a week. I was working eight days a week. I had no kids. I had no life other than my, my Reba Sests. And I remember thinking, I'm 37 years old. I had no kids. I have no life. Surely I don't have to work seven days a week, ten hour days. Live on airplanes being a different city every day for all of us. So I decided to go back and and and changed my life. I went back until I keep and said, look, I got to take a sabbatical and and figure out how to have kids figure out, you know, what I'm going to do the rest of my life. And he said, no problem. So, but being an officer for a public company took me about four months, a backfill myself, backfill myself, and they both had sales and marketing at that time. And then I kick off the company's new fiscal year. So I did that, and I left the Reba in November of 2000, and at the same time the dot com explosion occurred. And there was consolidation in the market. Reba was doing fine, but there was still consolidation in the marketplace. So it didn't make sense for me to go back in an operating role. And I was fortunate enough to meet these people called money, meaning and choices based out of San Francisco, where they helped people who have gone through, you know, maybe a dramatic wealth changing moment. Like I had done with the Reba to help me figure out when you do the rest of your life. And they said to me, I remember when I first met them, they said, so Rob, you've done a Reba. What are you going to do now? And they said, oh, I'm going to be CEO another startup or become a venture capitalist. And this is great. They said, why are you going to do that? You can do that because you want to or because that's what people like you do. And I said, probably because that's what people like me do. I guess that would be fun. And they said, this is, well, that's great if that's what you want to do. But let's future pace because I was 37 at the time. Let's pretend you're 70 years old. And you're looking back over the last 30 years of your life. What are you afraid of? I thought, oh, maybe afraid of regret. I said, good answer. That's what most people are afraid of. Well, maybe I just went down the path that was planned and I didn't try different things. And they said, well, to avoid the regret, why should you do something that you have the ability to do that others may not yet? And they go, what do you mean? They said, well, people spend their lives generally chasing two things, money and time. And what's he achieved money and time? The question is, what do you do next? And you would think that people who achieved money and time are super happy in the world. Or if we tell you statistically, a lot of people that achieved money and time are not that happy, right? That landed on me. I was like, well, shoot, I don't want to be one of those people. Yeah. And I don't think I would be able to help the optimistic positive person. I wake up every day, excited about the day. But it did make me think I should do that exploration. So they took me on a little offsite for a couple of days and we went through a process that they have. And from that I came up with seven different things that maybe I'd like to try over the course of the next 30 years. And so the thought was, well, maybe try those things now. And then like them, great, if not, you know, you can always go be your son of a stuff. So I ended up doing that. It took a few years and knocking down a few of those and doing those things. And along the way in 2003, I got an email from another founder who is himself and my five other people. And they were, I wanted to monetize six degrees of separation. I thought, what a great model for the internet. Six degrees of separation. So I then searched them out, found out that they were talking to Sequoia Capital about a series A fundraise. And I knew the folks over at Sequoia and they put me in touch with the founder. We had lunch and or breakfast. I forget which. And he, after that, I had my rebuke cache A, obviously. And he asked me, if I would invest and join the board. And I had never done any type of private equity and investment. I was in some venture funds, but not any part. But I decided to do that because I didn't want to not do that. If I can't, I can't take a board seat and not be a believer. And I was a believer. So I did that. And that company ended up being linked in. So I was on the board of linked end. In those early years, I got a chance to see the company gets a point of profitability and a cash flow positive. And I'm going to, and two things occurred, probably about my third year there. I was at the time very interested in exploring those seven things. And I was always distracted. And looking back now from all the work that I've done since then, I wasn't the best board member. I wasn't the most active. But I was active enough to really understand things and and and participate where I felt appropriate. But I even sent a note to read about five years ago. So hey, sorry, I wasn't the at the same level of of intimacy that I could have been now knowing how to be a real board member years later. And he was in no way sure. But that was an interesting learning there. You know, the other thing I learned a very important lesson as well, LinkedIn is probably worth sharing with you. Yeah. It was a gentleman I was working with. He was head corporate strategy. He was 22 year old kid. And LinkedIn was growing like a week. And I knew LinkedIn was going to be something special. And his kid, I came into for a board meeting one day because it came up to me saying, Hey, Robert, just want you know, I gave my notice today. I'm leaving. And I said, you're leaving. This is going to be a rocket ship because yeah, but the company, I'm going to go to I think it also is going to be a rocket ship. And I just want to go work with my friends. I went to school with them. I feel like I'm with my friends. I go, I don't know. I think you're making a mistake. And he said, he said, Hi, I kind of follow my heart. I think these guys will be okay too. So I said, I said, All right, great. Well, where are you going? And he goes the Facebook. Wow. And I said, Facebook, you're going to leave LinkedIn for another classmates.com. So I said, you know, a small market segment I thought, you know, no, no, just credit to claspets.com or here on Facebook. And he said to me, he said, he said, Hey, Rob, I spoke to that over there. I told him stuff higher, I help him and we'd love to have you come over and meet, meet the founder and maybe do the same thing here that you do over there as you do here at LinkedIn. And I said to him, I said, great, send me, send me a note once you get over there. I said, but I said, one social network, is it enough for me? Yeah, probably. Wow. So you never follow it up. Okay. Now. I thought that I needed more money or more things to do, but the last thing I learned was, you know, when you think you know everything, when you don't keep an open mind, great opportunities come and go. And you may not even know it. So the advice that I've given all the people that I've worked with over the past 20 years are, keep an open mind. Don't always assume you know what it's going to be like on the other side. And I can't tell you how many people are dismissive of taking in new concepts and new ideas and new way of doing things, whether it's, I've interviewed top salespeople, I try and teach them the curiosity thing. I don't need to be, I know everything here is about sales. Or let me teach you some things about leadership or about culture. You're a revert culture. We know about culture. And it's just like those opportunities to learn something are valuable and it's interesting to see, I can always tell who's going to hit it big because people who are open minded and stay curious of the people that really end up getting to where they want to like. So that's my thoughts on LinkedIn. Great. On the seven items that you were exploring, any highlights or lowlights from that time in between Areba? Well, I mean, some of them were things like, okay, maybe going into the movie business, making a movie. Okay. And I learned to make a movie, of course, three things, a great idea for the movie. A great team of people. And funding. Well, that's, and it runs about four years cycle to do it for it all together. Well, startup companies are essentially those same things. A great idea. Great team. Good funding. Four years. Four years really kind of get it to a material shape. So I thought that was kind of fun. Politics was another thing that I thought was kind of interesting and fun. Education was kind of fun. So I was a mentor at Stanford's GSB school. And even still, every once in a while, I bury you. I was a guest professor there for selling through curiosity. Occasionally, hasn't it come? Nice. One of the most interesting things we don't need to come back on or anything. But what you said about meaning, meaning, money and choices, how they, uh, money and choices. Money, meaning choices, was the movie. How you said it like a movie is an idea, a team, and four years. And like, that's like a startup. I just thought it was interesting that like, and it sounds like you didn't pursue the movie path. No, I did actually. Oh, you did? I, uh, what I did was I leveraged my network. My financial advisor was also a small advisor for John Davis, who was Marvin Davis, his son, Marvin Davis, was the richest guy in L.I. back 30 years ago. Marvin Davis just died. John Davis is his own production company. And he should, he produced a lot of movies, you know, Marvin Davis own Fox. And then, uh, John Davis shot movies that were age appropriate for his kids. So all the Garfield movies were John Davis. Wow. Um, fat Albert was John Davis. So what happened was, as I met John Davis, I talked him into me being his assistant. And I shot got to learn. Yeah. Yes. I wrote a shot. For about a year, I'd fly down whenever I wanted to. I'd go and do go on set listening to negotiate deals, stuff like that. And then one day I was like 10 o'clock in the night. I'm out of a movie shoot in some place in L.A. and, and John went home to his wife and kids and I stayed there with the producer. And, um, and it was like a cold misty night. I'm sitting there watching. I'm learning everything. But I says to me, the producer says, what the hell are you doing? I go, I guess we're all trying to get where you are. Are you trying to get where we are? Yeah, I guess I'm just trying to start over again. So I realized all I was doing was trying to relive the glory of taking something from nothing at the building. Yeah. And I thought, you know, it's true. I don't have to go, I don't have to go build at a holding market. I don't have to go to China and have to come at a restaurant here. Yeah. Or, you know, let's have a passion for food. Yeah. But, but there's still that right or wrong about any of those things, but, uh, so, so, so, so I tried it for about a year. Yeah. You gave the shot. You realize it wasn't your cup of tea. I tried teaching a Stanford. I realized that's sexy. You have to be there for nine months out of the year. I don't want to do that. Yeah. And so I didn't do that. We did politics around all sorts of makers campaign. I go for a variety of reasons. Yeah. It sounds like you have no regrets because you, you tried them all. No regrets yet. I didn't try them all. I never was to move to Italy and study languages and art. But, quite honestly, I learned that what I love to do is I'm a builder. I love to help build a company. Whether it's being directly, intimately involved with a company, whether it's being on the board or being an advisor, whether it's investing in the company, as a company called Blue Managerie, which I think they had the most incredible product in the world. You know what cell phones were at the landlines? Blue Managerie distributed power is to power plants. Clean, green distributed, reliable. And I got so excited. I became a major investor in blue. But more than being an investor, I'm just a believer in the team. And the people and the product. So I've done stuff like that. You know, about 10 years ago or 12 or dozen years ago, I kind of found my sweet spot, I thought. And that is companies, young entrepreneurs that have a great idea, whether it's in people analytics or whether it's in a variety of other places. In some cases, they may have anywhere from a million to 10 million of annual recurring revenue, subscription revenue. And I just haven't figured out how to reach that growth philosophy that you did out of REBA. Yeah. And I've been fortunate enough that I've been able to replicate some of those things now several times. As of some of my REBA co-founders, IEKEE had Docassine. He did that with Docassine, also part of the State Department, when the Land of Secretary did. Yeah, safe air. And I was able to bring some of the concepts over to Bloom 15 years ago. And then I did something in the people analytics space. I did something in the CLM space, the company called Agiloft. I did something in the cross-border payment space, a company called Eusez. And then more recently, about three years ago, I introduced to a young data scientist who was reinventing procurement of all things. Okay. And you've heard that song. And I heard that song, so I ended up getting and talking to him. And one thing led to another. I got super excited about the technology and the data science and AI work that they were doing. And I could see how impactful this was going to be, especially for direct materials. If you work on the indirect stuff that a REBA and cooped in those companies would do, but I also, when I talked to him, and I found out that the top three technologies that he used in the world today, to buy direct materials, which is 80 percent of all materials bought by corporations, was the telephone, email, and Excel. And now he had a team of data scientists that could simulate ahead of time and provide data science and human game theory to it. I got so excited. I said, I'd pull out page one, chapter one of the REBA playbook. And he gets so excited about that. He asked me to join him as a co-founder. And I did something I never thought I'd do. I call some of the original REBA go-to-market team. Yeah. I brought them in. I spoke to the venture capital. I brought in the financial strength to build a great company. And the company is called Arquestro today and alive and long going strong. And we have some big deal now in the works. So what are you doing with Arquestro and some of these other companies? And yeah, you're not just sitting back. You're not just pointing things out. Yeah. I'm a co-founder with Ed Misagra and the data scientist. I'm a board member. And I like to think of myself as something called me like an executive chairman, meaning, I'm involved. But I probably spend anywhere from 35 to 65 hours a week, depending upon the week. Working with Arquestro, helping to build a team, helping to work with prospects and customers. And she had a vision helping to work on a business and operations. I have a REBA, but we focused on building a great company by focusing on three legs of the stool. It was a great engineering and technology. Great go-to-market and great business and operations. operations. So I'm always thinking how do I help the company in all those areas where I'm helping interview some new engineers or all whether I'm working with some new, some of the sales people with some prospects or what have you. So I'm doing that. That said, I've got, I realize other day, I've got five companies that I'm actively working with. My tester was by far the biggest one, but I'm co-founder of a company called True Parity, which is a whole new platform for it's disrupting the whole market of how people find real eters and how they conduct transactions, real estate transactions. For example, 80% of the people that go to sell their home or buy home, they find a realtor. He's either a family member, a friend, networked neighbor, but do you think all those people are the best in their market space? No, no, it's not a way to see the highest quality. In fact, if you talk to the industry analyst, they say 90% of all real estate sold in America, residential is handled by the top 10%. That 80% picket that way, they end up going through two or three realtor. If you think about it, who does know? Who does with the right? These researches got to be done. Do you really want to go to that research? Do you want to say, "We easy to ask your neighbor, your friend or something like that and give them a shot?" But one of the most valued assets is your home. Why would you? Why would you give it to the subpar salesperson? That's the best way it's to the best reps. All the online platforms that came out, all positions themselves at discount brokers, which is crazy because now you have the internet is the discount brokerage firm competing against the top 10%. What if we take those five magic questions and we apply those five magic questions to the top 10% of the brokers in the country? We did. We said, "How do we create an online platform that you're going to love that's going to foster more money for you?" They told us and we built it. The company's fostered parity. The theme of those five magic questions, we did that and I just walked. Yeah, and then there's a company that's called Save Naturally that's changed the way. Coupon, they've created a whole platform that makes a better platform for product manufacturers and for retailers and for users who wants to go coupons anymore or try and remember where they are. So, the greater a platform that. And then I got a year and a half ago by someone said, "Hey Rob, we're creating the LinkedIn for the Creator Economy." The company's called Creator Land that based in Los Angeles, they've got a ton of Creator experience. They've got over 30,000 members already and growing at a rapid pace. 390 million people in the world are creators. They create content as you're doing right now. And they're and these are people who do quite well financially and yet only 3% are on LinkedIn because the LinkedIn platform was never designed for the Creator Economy. When I learned that and he persisted, I actually saw the momentum inside of his product and saw that the metrics were comparable to that of LinkedIn when the early years. I said, "Okay, so I've got the newer Reba, I've got the new LinkedIn." If I imagine questions. If I imagine questions, so I keep pretty busy with all those things. Yeah, love these ideas and the excitement that you share with and you've seen the, you've been on the journey before and now you're reinventing it and you're helping other entrepreneurs and other sellers to bring them along of what you've learned and it's pretty cool to see you repeating that. Yeah, I've been solving things. I should write a book because I've gone from rags to riches from growing up in a very humble environment in Rhode Island. Here we are now, back at Rhode Island, as we're doing this, but it's been an amazing journey so far and a lot more chapters to be written. Absolutely. So Rob, to close out this phenomenal conversation and put a bow on these deal stories and outcomes that you've shared with us would love to understand from your perspective for leaders and sellers who are less experienced or have been in their career for a while and are open-minded but haven't gotten to where they wanted to go. What might you suggest to them to help them see some of these outcomes? Well, I think what I would suggest, I mentioned some of them along the way here, but in trying to bundle them together, I'd say, keep an open mind. Keep an open mind to learn new things and try new things and the open-mindedness and curiosity will can drive a lot. I'd also say in your sales career learn how to create urgency and scarcity. Okay. And also be conscious of the different types of sellers that are out there. There are some people that are great at early stage companies, they call them sometimes referred to as hunters. Yeah. And then there's people that are great at getting large orders from existing customers and some of the business items called farmers. Different ages and stages of companies require have needs for both or one or the other. So be very conscious of that. I think the other thing is you got to create an inspirational environment. You have to inspire with people if you're going to lead or manage them. They can't be about fear and anything that comes to go out and good people perceive as negative. People want it in this day and age. They want to get up every day and be excited about not only what they're doing but who they're doing it with. They want to enjoy the journey. And they love to be inspired. Those would be some of the things that come to my mind. There's a book called Sales Leadership by written by John McMahon, the famous had a sales for multiple different companies. And a former board member of Snowflake or had beer. He's written a great book on how to lead and manage and sales. Bearer Ryan selling through curiosity is a tremendous resource and how it's published lots of stuff and doing stuff like that. Yeah. I'm not going to be Ruth's but call for you. I spend your time. I spend your time. You all have so much time. And then and then scarcity and urgency. You get a you know customer eventually you'll sell them all but I'm going to figure out who should be your first 10 customers. Who should be your first 20. We actually put together at a Reba a design to market penetration plan. But we said our first four customers are going to be close to home right here in Silicon Valley. There were 72 fortune 1000 companies in the Bay area. So we said a sell to that then we don't want to get an airplane. And once we get those four then we'll go and ask them to go to Europe. After you go to Europe then we'll go to the rest of the world. So you know and when you're able to explain those things to customers and you'll use that as an opportunity to create scarcity and urgency. Great things can happen. Okay. So bring them along on the journey and make it simple. And I also have a new one that I've learned myself over the past 10 years. Yeah. I'll be honest with you. 20 25 years ago I could not see myself hiring a salesman or woman. Yeah. Salesperson. Yeah. That maybe had been in business doing it for 20 years or longer. Okay. I had this general thought that if they've been selling for 20 years and they were so later to sell maybe they weren't that great. Okay. Well what my learning is has been you know great salespeople love to sell. Just like a great engineer does want to start to go up the engineering management. They just love the engineering. Yeah. And and with the days now of of COVID behind us but but it being a video conferencing world with zoom and teams and what have you. There is so much great talent. Regardless of age from the 20s to 30s to 40s to 50s even the 60s people that just not really get what they do and love it. And so I learned not to judge a book by its cover regarding age. Because I realized that that it's really all about the the fire and the belly that's really going to make someone's impression. successful enough. And whether you're young or whether you're older or whether you're middle age, your age brings a certain set of assets that you get to bring to the party. And learning how to leverage your own personal assets in the sales process is something that I think is also very fun and important to do. You've had these amazing phases of your life and career so far, looking back and maybe looking forward for the audience, how might you recommend that they look at spending their time in their 20s and their 30s and their 40s and 50s, etc. We have the audience who are sales professionals, sales leaders, sales representatives. They're always looking to get better and learn. They consume this podcast and yeah, I'm curious looking back how you might give that advice. I've heard this question for the first time. I'll just speak top of mind. I think people in their 20s, ruthless qualification. The high energy, know your product, but be a ruthless qualifier. I think that is what's going to set you apart. In your 30s, I think it's the ecosystem that you've developed maybe, where it allows you to do things more efficiently because of your ecosystem that you've developed, whether it's with part of all the companies, friends, whatever. In your 40s, I think the power starts turning into storytelling. The reason why I say that is, you've now probably closed a few big deals. You've got some great successes under your belt. The people who you're selling to might be of similar age to you. They're growing up their corporate ladders and it's now more of a peer type of sale. The storytelling becomes a very thick part of selling as opposed to selling features and functions. In your 50s, leveraging your experience, but showing your energy, showing that you can take all of the assets that you've collected over the years and be able to optimally use them to be the most efficient ruthless qualifier, to be the most prolific storyteller, to have the most incredible network. Then I dare you to say in the 60s. People in the 60s, I see that I kill them. They have passion. They have passion for what they do. It's an art to them. They realize that they're not doing it because it's a job. They're not doing it for the money. It's transpired or transformed into being an art. A fine wine, how you really deliver value to a customer, to the company, how you leverage all of that experience that you've had to do that. Those might be some of the things that come to my mind. Yeah, that's a great summary and a way to think about life and it really comes full circle. How does legacy fit into the picture? Legacy is an interesting word. I'll tell you something that we used to talk about, but it hit me over the past year. That is, I heard about this book that was written a long time ago and read it and called The Secret. It's about manifesting your future. When I was 20 years old and I was in LA, I fell in love with Beach volleyball. I said, "Well, I would love to play Beach volleyball with all these pros." I'm 5 foot 6. I didn't grow up playing volleyball. I thought to myself, "How am I going to play volleyball with these people?" I thought, "You know, I don't go work hard. I want to try and retire by the time I'm 40. I want to try and start my own business, retire by 40, just when they retire you and off the AVP circuit. Then maybe I can mentor them in business and they'll play volleyball with me." Would you know what happened? I retired at 37. I built a house in Manhattan Beach. I played volleyball for the past 20 years. Five days a week with yesterday's Olympian, today's Olympians, so many pros. So you manifested it? You manifested it. And what I think about the material things that I've done in my life, it's been a manifestation of what I wanted, whether it was to have a great home here in Rhode Island, whether it was to have a beautiful family, whether it was playing volleyball, whether it was becoming a scratch golfer, which I'm still on that path right now manifesting. But when I started 15 years ago, I was a 27 handicap and today I'm a between a four and a five handicap and I'm just loving the journey. So it's back to legacy. I've built several homes. I thought they were a legacy, very a legacy homes. And I learned that life moves and evolves through different paths. And legacy isn't a thing. Legacy isn't a house. It isn't one particular thought. Legacy to me, is about happiness, love, and contentment. Am I content with how I'm living my life, how I'm impacting those around me? Am I having a life that's worth calling a legacy? I break my life now up into three things. The professional rob, the family rob, and the personal rob. And the personal robber, the things I like to do, whether it's beach volleyball, or golf, or playing chess, or whatever it is. My family, my wonderful wife, my wonderful children, my wonderful parents, my siblings, my extended family, my friends, you know, have that social life and that balance. And then of course, the professional quest to build and do. So that's my, so that's my, I'm hoping that my legacy will be that rob was an incredible friend, family man, a happy person that loved to build things, whether it's houses or companies, what have you. So that's my thoughts about legacy. I love it. That's a great thing to think about and a great way to end this conversation. So thank you Rob. You got it. Thanks.

Podcast Summary

Key Points:

  1. Rob DeSantis transitioned from engineering to sales, driven by a desire for higher income and leveraging his technical background and communication skills.
  2. He developed a highly effective sales methodology based on "ruthless qualification," time management, and prospecting during optimal hours, leading to exceptional performance.
  3. His career pinnacle was co-founding Ariba in 1996, where he applied his sales strategies to close foundational deals, making the company cash-flow positive within months.

Summary:

Rob DeSantis began his career as a mechanical engineer at Hughes Aircraft but sought to augment his income, leading him to sales through Herbalife and stock brokerage at Drexel Burnham. These early experiences taught him resilience against rejection and the critical skill of "ruthless qualification"—focusing only on high-potential prospects. He transitioned to selling engineering software, where his technical knowledge allowed him to excel, quickly surpassing his engineering salary. His success led to a role at RASNA Corporation, where he dramatically exceeded sales targets by implementing disciplined time management, such as prospecting early to reach engineers before meetings.

DeSantis later moved to Germany to expand sales internationally, learning to navigate cultural differences. After RASNA's acquisition, he co-founded Ariba in 1996, recognizing an opportunity in internet-based procurement for indirect materials. Applying his proven sales tactics, including creating urgency and leveraging customer advisory councils, he closed key early deals with companies like AMD and Cisco. Notably, within five months, Ariba became cash-flow positive after closing several multi-million dollar contracts, marking the most significant deal of his career and establishing the company's foundation. His journey underscores the power of combining technical expertise with disciplined, customer-focused sales strategies.

FAQs

The most memorable deal was a $10 million sale for Reba Technologies, which he co-founded, with a sales cycle of about four and a half months.

He started by exploring part-time opportunities to augment his salary, including Herbalife and stockbroking, before a consultant suggested selling engineering software, leveraging his technical background.

He learned ruthless qualification—focusing only on prospects likely to spend money, avoiding time-wasters, and using techniques like early morning prospecting to reach engineers effectively.

By applying ruthless qualification and time management, he closed 41 deals in his first 90 days, far exceeding expectations, which led to a promotion to head of sales.

He used five magic questions based on curiosity to shorten sales cycles, increase order sizes, and improve predictability, helping validate and grow Ariba's business model.

He found that sales fundamentals like value communication were similar globally, with minor logistical and cultural differences, and his neutral American background helped build a successful European organization.

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