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hey paul thanks for joining us today as a way of getting started give a little background on yourself sure brian pleasure to be here my name is paul lesser i live in westchester county new york 25 25 miles north of midtown manhattan with my wife two teenage daughters and our dogs have a wonderful family life here i got my ch my start in sales my dad uh was a jewelry retailer and i grew up working in the jewelry store in williamsburg brooklyn as a young teen worked in the store all the way up through graduating college uh when i decided at that time that i really did not want a life of a retailer and um had a fraternity brother who was working for a t selling phone systems and i asked him if he can help me get a job at 18t and there i was three weeks after graduating college uh selling phone systems or working for a t well that jewelry business i mean visit jewelry is highly negotiable right yeah jewelry is highly negotiable i started really as a 13 year old it was more just watching and gift wrapping and working the register but that experience working in the jewelry store watching that face-to-face interaction and negotiation um was invaluable and part of my dna well that's it because if you don't have that type of experience you don't really understand how the world works yeah you know i i agree it's also very interesting because the customers come to you they walk they walk into the store and they have a need immediately upon walking into the store and the the negotiation is face to face where what i do today in corporate sales it's a lot of prospecting and a lot of defining the need and it's it's not a lot of face-to-face especially at the beginning of the sales process yeah and but both are pretty still emotional decisions and jewelry is much more of an emotional decision yeah i i agree but they are similar in the fact that um you know they're still a want they're still in need there's still a gap there's still a quote-unquote problem to be solved so that's why in a lot of sense i go back to my heritage of working in the jewelry store when i'm out there negotiating you know seven figure deals yeah i think it's a great training you know i sold shoes in high school and it was good because it wasn't just ladies shoes and it wasn't just men's shoes it was both and it's great experience you know some people want to negotiate the price and you know shoes is not as negotiable as jewelry yeah that is uh that is that is very true i mean i remember as i got older in the jewelry business and i was actually doing some selling you know having to call my dad over and say hey dad you know is actually i called him ronnie in the store never call him dad in the store you know you know and um yeah and um we would make decisions and we would negotiate together it was it was it was a lot of fun precious father-son moments as well that is cool and what did you like about b2b sales so what i really liked about b2b sales first and foremost was the fact that i i really made the decision that i wanted to spend time with my children and i wanted to be at their ball games and i wanted to be at their concerts and my father wasn't because he was working crazy hours in retail so i i really enjoyed the hours of of b2b and i also enjoyed when i started my career with a t the whole um cold calling methodology and that initial sales training that i got at 18t as a 21 year old out of college and did you have any call reluctance yeah i think even to this day honestly there's a little reluctance exactly exactly but i think i learned very very quickly not to take it personally my first day at att they put about 12 of us in a little horseshoe and they gave us a phone and a headset and a list of people to call and i was prospecting literally eight hours a day for the field sales team generating leads for them and it was a wonderful experience you dealt with a lot of rejection but as a young salesman uncovering a lead and having to engage with the ae who was in the field selling and say hey i got a lead for you um that part of it to me was really exciting yeah so it was a team sale it was it was a team sale a lot of times the field sales person would take the cold caller so to speak myself out into the field on particular opportunities that i had uncovered myself so it was a great great way of learning and then the other part that i really enjoyed was 18t lewis out to cincinnati i spent about nine weeks in cincinnati doing uh some really structured sales training and some of that training i still use today and have you covered uh other geographies other than new york metro yeah interestingly enough i i really during my career have not been um focused on geography i also have not been really focused on vertical markets i work for a company today nectar services corp for about a hundred people and if you want cover and opportunity regardless of where it is as long as another sales rep is not um attached to it in crm it's your opportunity to work wow so kind of an open territory it it's an open territory i think you need to be focused and still put a plan together and still you know have those 10 or 15 accounts and put a prospecting plan in place but yes in essence as long as it's not in crm i could go ahead and see if i can uh create an opportunity for myself and when did you make the transition into enterprise sales from kind of that inside setting appointments to outside closing big deals yeah so i graduated from uh the prospecting and i became an outside sales rep for a t and the way that att was structured at the time was you know you sold any organization within a certain territory at that time i did have a territory between zero and 40 phones somebody had 41 phones that went to the person who sold between 41 and 80 and if you're 81 you so so you you get my point right big company joy big company detroit but what i did learn from that experience is i enjoyed the bigger sales not necessarily because they were bigger commissions they were just more complex and there were more people involved in in them it took more thought and preparation and i really enjoyed that and where does that come from given that you started in retail which was transactional they probably if they left the store that day they probably didn't buy i i would agree with that yes [Laughter] to enterprise where they don't buy on the first visit yeah you know i think you know it's interesting because a part of me is very patient and a part of me is not very patient clearly in my business life i need to be much more patient you know i've done a lot of reading on the art of sales and the art of complex selling and i i just really fell in love with it i just really enjoyed the challenge and that's why for me right now um the bigger the better i love those seven figure deals and listen i've also worked through um a place where a lot of it used to be capex perpetual and now we're in an opex subscription world so um that's been a learning experience as well yeah and do you focus solely or exclusively on seven-figure or large no no i mean i sell into the fortune 500 space i would say that my average deal is probably around 400 000 in total contract value over over a three-year term selling selling software um i've sold some um some seven figure deals those are you know 12 to 18 months sales cycles so you know if you use a baseball analogy you definitely need some singles and doubles in there because if those 12 to 18 month deals don't close you still need to have enough in the top of your funnel to make your number and as far as like the passion for that where does that come from you know are you a chess player do you just like ahead or do you you know there are strategic people that you know but most people are circadian every day you know you get up you work you eat you sleep yeah i i would say that i'm an average chess player um i think it comes from my competitiveness okay which started from um you know my days of being an athlete i enjoy um beating the competition i have a ton of respect for my competitors and a lot of my competitors are very viable and have solid solutions i think it comes from that i think it also comes from being able to sell my unique value and i think most importantly for me you know coming from a world where i used to sell features and solutions now i'm selling outcomes and when your mind flips from a solution feature sale to selling an outcome um i just enjoy that i just have passion for that and you know just another piece of the puzzle brian is you get to know your your your prospects who might soon become your customers and i care about them i want them to be successful and if they can be successful and i can help them be successful to me it's a win-win and was this an epiphany that you had along your career or was it always this way because a lot of reps once they do a big deal then they fall in love with it and that confidence that they figure it out but until then they're like i'll take the medium and small deals i i wouldn't say it was an epiphany for me i think for me it was the more complex sales being more challenging taping taking more brain power i thoroughly enjoyed doing the discovery process and asking those open-ended questions and potentially even even finding problems during discovery that a customer or a prospect didn't even know that they had i think it's the complexity of it and another piece with brian is you know i also consider my sales career a hobby as much as i consider it to be my career so to use that chess analogy you know chess might be a hobby fishing might be a hobby not that i don't have hobbies but but i really view it as a hobby and and it's it's it's a wonderful thing it served me quite well would you characterize it as a passion also definitely a passion as well and listen at the end of the day you want to help your customer you want them to you know reach their outcomes you want to fill those gaps when you get that commission check and it's a nice number it's it's it's wonderful it's that's that's a wonderful thing as well you know the larger the deals usually the larger the commission checks yeah so being money motivated helped along the process i i think money motivated help but it's i'm not solely money motivated i think when you help your clients achieve a goal or achieve an outcome the commission is a byproduct of that and who do you typically or who do you feel most comfortable talking to is it executive is a user is it on the economic side or the technical side so i've done a lot of studying and i've had a lot of conversations with procurement and i i thoroughly enjoyed the procurement conversation which usually comes at the end of the cell cycle i enjoy the conversation i'll tell you why i'll tell you why brian because if you if there are 12 to 15 people in the business the users who are sold on your product and they want your product and you've done a good enough job of justifying it to them negotiating with procurement becomes easier because the business is putting pressure on procurement saying hey let's get this done we want this solution so i find those negotiations to be really intriguing and and i enjoyed the discovery process as well and one of the things that i learned early on in my career is just because somebody doesn't have an impressive title just because somebody might be lower on an orb chart than others doesn't mean that they're incredibly influential on the decision same for somebody who might have a vp title that doesn't necessarily mean that they're respected within the organization and have power so i enjoy that whole power shift and understanding who has influence and power within an organization and do have you developed a sense for that i think so i don't take i don't take it for granted um i try to find and i think it's incumbent to find a champion within your account i would say just about every if not every large deal that i've sold i had a champion who would give me some inside information regarding who i should be communicating with making some introductions letting me know who people are um talking to me about the buying process and how the technical decisions get made as well so i think it's incumbent to have a champion with in the account that's going to help drive your message internally as well and what i've found with large complex sales is you have to have a what i call a good bs meter because your time is all you have and you can only work on so many deals within that window of time so you have to be able to judge both the people and the deal what's the saying the saying is uh when slow lose fast you need to know quickly one of the determining factors for me is if i'm working with a prospect and i'm doing a discovery for example and let's say there's four people on the discovery call and we move on to the next phase which might be a live demonstration specific to what you learned during the discovery the pain points and the gaps if those people are not introducing you to other people within the organization as time goes on and if if four people don't become eight don't become 12 quickly and if you're also not communicating with other lines of business besides the line of business that you were originally introduced to it's probably time to have some tough conversations and potentially cut court and find another yeah because a lot of times they want to go you to go steady with them meaning don't go rooting around the company they'll get it done that's true a lot of times they want you yes a lot of times they want you to go study with them a lot of times they're they're using you and i don't mean this in a bad way business is business they're using you to um get a lower price from someone else from someone else that they really want to buy from sometimes they want to learn about feature functionality that you have that maybe they can go back to the company they want to buy from and say hey you need to develop this for me if we're going to do further business together so you need to be able to root that out quickly and what is um the most challenging part of these deals wow i think the most challenging part of the deals is just understanding exactly where you are in the deal and that's where i lean on colleagues mentors leadership within my organization where we can actually sit down and lay out the org chart where i am in the sales process who i've spoken to and maybe come to a collaborative decision on where we are i think that's the most difficult thing for me sometimes you get off a very positive demonstration where you nailed it but perhaps you didn't and you don't know so and and that's where by the way that champion within the organization comes in because that person if you find that person will give you honest feedback right yeah because i always when you could do a face-to-face call that walk out to the parking lot was i la that is such a great point that is i could almost tell if they were going to buy if the champion walked out to the parking lot with me if they just wave goodbye at the reception desk yeah and and you know something another is when you leave the conference room if on the way out they're introducing you to people in cubicles as you're walking towards the door that's another huge um yeah i i agree i agree so you know some of it is interesting some of it is is is certainly sales right certain some of it is but some of it is the the personality of it um and just the shape and form that the sale takes and those subtle things an introduction a handshake eye to eye contact you see somebody taking notes those are very important indicators yeah and people tend to ignore those but you're like i'm always looking for an asset test something to determine you know is this a a deal or is it a b deal or is it a phony deal are you just calling fodder so let me learn from you a bit what are some of those acid tests that you would look for a lot of them you know are they asking for a next step versus you have to suggest to next absolutely yeah you know are they raising your weakest point and your competitor's strongest point exactly are they buying into your strongest point yeah i think your point about asking for next steps and um just getting a feel for their if you have to ask for next steps what's their reactions right right well we'll get back to you or right yeah and and i also find you know interestingly enough in my sale listen and i'm very cognizant of my company's money and resources and um pre-covered i'm very cognizant about travel and travel expenses and hotels but there is a point in time where it does make sense to have a meal together and learn about people and learn about their families and have that sort of talk about the kids and talk about the dog and talk about potentially the house they're building and i find that if you don't have that conversation during a complex sale your chance of closing the deal is diminished and again it's being respectful of your company's resources but there is time and a place for it as often as you can because and that the other asset test is do they want to talk with you yeah yeah agreed agreed but also i've also learned this brian that you know i you know i can have the greatest solution i can have the greatest marketing message i can have tremendous rapport with somebody if they don't have problems that i can fix if there's not a point a and a point b and if i can't help them get from point a to point b it doesn't matter how many dinners we have it doesn't and there are false champions the people agreed who want to hear about the kids and want to talk about their house but love a nice steak dinner but you know can't get anything done i think you know when it's real right much like in that jewelry store when the guy is balking at the engagement ring the fiancee kind of knows what's going on right and and here's an example back to the jewelry store if the person really wants to learn about diamonds and really wants to learn about the quality of the diamond the size of the diamond the way that it's cut your chances of closing the deal are a lot better if somebody's just coming in and they're picking up rings and looking at them and asking how much devices so yeah yeah kind of that transfer of ownership where they're visualizing the outcome absolutely absolutely pulling you into it and help me out teach me the difference absolutely absolutely you know and i think another piece of it also is uh back to something you'd said before is that you know i'm really i'm really a people person i love meeting people talking to people and you know in the jewelry store it was more one-on-one two-on-one uh in this complex sale that i'm in you know you're meeting 14 15 sometimes upwards of 20 people and uh if you have something of value you get to know them and that's that's that's a lot of fun and listen i've made i i've had a lot of opportunities that did not turn into closed business but there are people that i still keep in touch with and i learn from and i've created some relationships there so there is something to be gained even if the deal isn't closed although of course that is the ultimate objective and what would you say is your weakness that you wish you could really get better at wow um i am not the most patient and in these long sales cycles you really need to be patient i've learned in my corporate world that there's a process that you need to stick to the process for example finish the discovery before you start providing a live demonstration don't all of a sudden during this discovery find out that you can fill a need and stop doing the discovery and go into a demo so i've had to teach myself to be much more patient and um i think i am because i have to it's the only way to close these kinds of deals and have you found a particular way of doing that i think it's following a process and that's really the way that i've done it is if you don't skip steps in the process and you understand that not only is there a technical sale to be won a lot of customers don't know how to transact business within their own organizations so sometimes you have to walk them through how they can go about getting the deal closed and then there's also the technical sale so you have to win a couple of small sales in order to win the larger sale and that takes time and patience and that's it and i try and convey this because larger deals are just one big trap after another and they're so easy to fall into whoever's buying that jewelry versus whoever's getting that jewelry are you great because the person who's getting the jewelry is very excited absolutely absolutely personally absolutely jewelry is a little cautious it's actually best when the person who's buying the jewelry is there with the person who it's being bought for that's that's an indicator that you have a good chance of closing the deal [Laughter] and when do you get the sense or do you have your own asset test to determine when it to walk away or de-prioritize um i i can't say it's something specifically i would say at this stage of my career it's something that is um just sort of a natural feeling that i get when i do feel that way i do ask some tough questions sometimes like can you please introduce me to x i'd love to meet some other folks within your organization so i think there's a time and a place and for me it's more instinctual that you have to at that time start asking some tough questions to really understand where you are in the sales process and tough questions aren't tough questions unless the you're not dancing the same dance with the prospect and have you ever like gone through the whole thing and it doesn't happen yeah i mean there are times where it could be many reasons it could be a a change in leadership um delaying a potential opportunity it could be i've had i've been in positions where you're getting to the end of a sales cycle only to find out that a customer is going to be bought or going to be sold so yes there are definitely times where you get to the end of the sale cycle you have that deal forecasted to close and sometimes it doesn't but i think that's why it's important that these sales be team sale sales so your leadership your mentors the people within your organization who you're forecasting the deal know exactly where you are in the deal and and they're not emotionally attacked as emotionally attached as you are they're not as emotionally attached to the deal but they are consistently asking when it's going to close especially towards the end of a quarter and customers don't generally care all that much about end of quarter they're on their own time frame so you know i i you know personally i don't like those questions can we pull this what do we have to do to pull this deal in before the end of the quarter that is not to me a way of um and of what i would say is a lot of times is i put my prospect's hat on i view the deal from their perspective their perspective isn't we need to get this deal done by march 31st but i i always found talking through a deal with a colleague they tend to see what the blatant thing that's missing because they're detached and that they don't have a dog in the hunt you know it's interesting early in my career i used to put together an org chart and on the orc chart i used to list whether the person had influence or power or was a decision maker and if they had influence of power their level of influence or power and then i would sit down with colleagues and we would actually have a conversation about each person and sometimes in conversations i was wrong in believing that somebody might have been a little bit more influential than i was and that's why you're right when there's somebody you can talk to who's not emotionally involved in the deal that's a huge huge help and that's why these deals are team deals yeah cool hey paul i really appreciate your time today where can people go to connect and follow you so paul lesser you can find me on linkedin i love talking sales so if you ever just want to ping me send me a linkedin in mail and have a sales conversation i'd be happy to chat