The Future of Sales: Trust, AI, and Relationship Capital with Drew Sechrist
In this episode of Thoughts on Selling, Lee Levitt sits down with Drew Sechrist, CEO of Connect the Dots and an early Salesforce employee, to discuss the evolution of sales from the "No Software" era to the age of AI. Drew shares insights from his time working alongside Marc Benioff, emphasizing the critical role of "osmosis" in learning sales skills—a benefit he fears is being lost in today's remote-first work environment. He argues that while technology has made many aspects of sales easier, the loss of in-person mentorship and hallway conversations has made the profession harder for newcomers to master.
The conversation pivots to the future of selling in an AI-dominated world, where Drew asserts that "trust capital" is the only durable moat for sellers. As AI automates routine tasks, the human ability to build deep, high-stakes relationships becomes more valuable than ever. Drew explains how his company, Connect the Dots, is helping sellers leverage their "relationship capital" by mapping network connections to engineer warm introductions, moving beyond cold outreach to a model based on visibility and trust. The episode concludes with a look at how sellers can future-proof their careers by becoming "monodirectional connectors" who prioritize giving value over extracting it.
In this episode, I sit down with Drew Sechrist, the former Salesforce veteran who helped take the company from zero to $1 billion. Now the CEO of Connect the Dots, Drew is on a mission to kill the cold call forever.
We discuss the "Osmosis Deficit" facing remote sales teams, why you can't close enterprise deals over Zoom, and the "LL Bean" lesson on solution selling that I learned in a shoe department. Drew explains why your network is the only moat you have left against AI, and how to transition from being a "contact collector" to a true "connector."
Key Findings:
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The "Osmosis" Effect: Junior sellers in remote environments are missing out on the passive learning that created the superstars of the 90s and 00s. Leaders need to manufacture these "hallway moments."
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The Deposit/Withdrawal Ratio: Successful networking requires a 99:1 ratio of giving help to asking for favors. If you try to "monetize" every interaction, your network will dry up.
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The "Dinner" Metric: Technology can get you the meeting, but it can't close the 7-figure deal. High-stakes sales still require high-touch, in-person trust building.
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Network Visibility: The biggest waste in sales is cold calling a prospect that your colleague (or board member) already knows. Tools like Connect the Dots are solving the "visibility" problem of relationship capital.
Memorable Quotes:
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"I wouldn't want to start my career now... I survived because of osmosis." — Drew Sechrist
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"I get paid in dopamine hits when I connect two people." — Drew Sechrist
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"You can't sell something you aren't interested in... I wasn't selling shoes; I was selling an experience." — Lee Levitt
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"If you are just an information kiosk, AI will replace you." — Drew Sechrist (Paraphrased)
Resources Mentioned:
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Connect the Dots: ctd.ai (Free for individuals to map their network)
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Book: The Third Door by Alex Banayan
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Book: The Tipping Point by Malcolm Gladwell
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Concept: "The Jolt Effect" (Dixon/McKenna)
Call to Action:
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Map Your Network: Sign up for a free account at ctd.ai to see who you really know.
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Connect with Drew: Find Drew Sechrist on LinkedIn or email him at drew@ctd.ai.
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Lee Levitt: Welcome back to the Thoughts on Selling podcast. Today it is my absolute delight and pleasure to have Drew Sechrist join me to talk about all things sales. Drew, welcome aboard.
Drew Sechrist: Hi Lee. Thanks for having me. Great to be here.
Lee Levitt: Good to have you on board. Drew, I'm gonna pose the first question to you and then we'll get into the dialogue. Who is Drew Sechrist?
Drew Sechrist: I've had 30 seconds to think about it. Drew Sechrist is currently the co-founder and CEO of Connect the Dots. He's a former Salesforce early employee. Saw the, the first decade of Salesforce going from zero to a billion in revenue, which is pretty incredible ride. And took those lessons and put those into what I'm doing now with Connect the Dots and kinda have an interesting nomadic lifestyle. So I split my time between Miami, which is where I'm right now, San Francisco pretty frequently, and Belgrade Serbia pretty frequently.
Lee Levitt: So Drew, you've seen the sales industry change quite a bit from the early days at Salesforce when "no software" was a mantra and a T-shirt. I still have one that Mark gave me a hundred years ago. You've seen it change and we've seen how buyers have changed. We've seen how sellers have had to change. We've read The Jolt Effect and now we know that buyers now have all the information they need and they're incapable of making decisions, and I think you're on a path to fix that.
Drew Sechrist: Fingers crossed.
Lee Levitt: So let's talk about that. What's your current view of the field enterprise salesperson today? Is it better or worse than it was 20 years ago? Harder or easier? More fun, less fun?
Drew Sechrist: Yes. To that one, and yes to the third one too. I would say yes.
Lee Levitt: There we go.
Drew Sechrist: It's better and worse. It's harder and easier. It's just different. Things are harder. Different things are easier. Man, it's interesting, like would I want to start out my career now as a seller? I'll tell you one thing I wouldn't wanna do if I was starting out my career now, I would not want to go into the world where it's a remote-first environment. And I think that's not really coming to an end, but there's a new equilibrium that's happening. So during COVID, obviously everybody went remote 'cause otherwise we would pass each other the virus and that'd be bad. So that's over. And then everybody stayed in this remote-first environment for a long time. Candidly, like it was an employee's market for a while where the employee could say, I'll just shop my services wherever I want to go. And if you don't let me work from home, then I'm not gonna work for you.
Lee Levitt: Yeah. I need to be within three miles of the trailhead in Moab, so screw you.
Drew Sechrist: Yeah. I get it. There's a lot of like positive upside to that situation for human beings and for our environment. It is a little silly like hop on the highway and burn a bunch of fossil fuels to drive up to the city and go to work, and then drive home, and all the dry cleaning bills and the time wasted on personal hygiene and all that stuff. Although I don't think personal hygiene's a waste of time. I think it's a good thing, but...
Lee Levitt: Once a week, whether I need it or not.
Drew Sechrist: Yeah, exactly. But I would hate to be coming into this world of enterprise sales or B2B sales and not be in person with people. Because I know how much I got from... I moved from the East coast to North Carolina to San Francisco to work for Salesforce in 1999, and they plunked me into this office and there weren't many of us. There were only... [employee] every 36. So it was a small office, but we were all sitting next to each other. Mark Benioff was there and the other co-founders of the company and the early employees. Everybody was more experienced than I was. I was probably the least experienced person in that office, which was awesome for me because it was scary. I thought they were gonna figure out that I didn't know anything and I was useless and get rid of this guy. But that was also motivating for me to learn things fast so that I could be valuable and not get fired and not get sent out. 'cause I liked San Francisco and I didn't wanna go back to the East Coast.
Lee Levitt: And you had all that tribal knowledge to slurp up.
Drew Sechrist: Bingo. And it was great. I learned so much by sitting next to... I could rattle off the names of the people that were in that office with me, and they're very impressive people. Now, they've gone on to do really impressive things and I got to learn from them. And it was great. If I were sitting at home and I was just a remote person who was like, here's your territory, Drew, and here's your call script and here are your tools, and go do it, and we'll have a couple of Hangouts online each week. I wouldn't have learned any of that stuff, and I think I probably would've been fairly useless and maybe I would've gotten fired. But instead I got to learn from the best via osmosis. And that was incredible. I love that. Now, I am happy to see that there is this RTO return to office thing that's happening and a lot of younger, earlier in their career folks do want to be in an office now, and I think that's a great thing. Is it better or worse, harder or easier? I would say it's harder if you're not gonna be in an office with somebody to learn from, but I do think the pendulum's swinging back. People are going into offices and you should, if you are early in your career and you're listening to this, go get a job in an office and learn from the people who've been doing this longer than you and pick a really great company. It's the other thing I'd suggest. I happened to be lucky in picking Salesforce. I think I chose well, but I also got some... there was some luck of the draw in that one too, because you wanna surround yourself with people that you want the osmosis to be good, right? Things that you're picking up from them. So that's one thing that could be harder if you're not in person. That's probably one of the biggest things. The other thing that's harder is everything's changing so fast that it's like you could learn a set of skills 20 years ago, know that those skills are gonna be the skills that you needed to survive. And you could be like, okay, I'm working on this set of skills, and they're relatively static skills. That's not the way it is anymore, I don't think. I think you have to constantly be learning really fast. Things are changing so rapidly, so I think that's a difficult thing, but it's also an awesome thing. Things are changing so rapidly in a really awesome way. If you can figure out how to ride that wave, you can harness so much power as an individual in sales. And so I think it's great, but it's also hard 'cause you have to figure out... and there's no one place to look for all the information about what you should be leveraging. You gotta look all over the place and be your own collector. You know your education.
Lee Levitt: As a case in point, I'm doing some coaching with an SDR, Shay, who just finished his first year and number two in the company. Go Shay! He and I were talking earlier today and he said, I really wanna be able to pick up what's going on with the next set of conversations. He goes, and I don't have all the time in the world to listen to all the Gong recordings. I said, can you take the transcripts and just throw 'em in a Gemini and have Gemini do a summary? He goes, yeah. So you take 60 or a hundred hours of calls and in five minutes have the top five issues that customers bring up and here's what works and here's what doesn't work in response. We couldn't do that a year ago.
Drew Sechrist: No.
Lee Levitt: Maybe six months ago.
Drew Sechrist: Yep. That's a perfect example. If you're not paying close attention to it, these new capabilities will happen and you won't be taking advantage of them yet. And there's a lot of opportunity costs. 'cause you might eventually find out about it three or six or 12 months later and then you know, you lost three or six or 12 months.
Lee Levitt: Here's a personal story, Drew. I'm writing a book and I'm about halfway through. My co-writer is named Claude. Most of the people I talk to say, can you write a book with an AI? It's sure. You're not gonna tell anyone are you? Oh sure. That's gonna be a marketing differentiator for about five minutes. There are all these tools to de-AI your output. 'cause everybody's so ashamed that they used AI to write something and I'm actually starting to stop caring.
Drew Sechrist: Yeah, because what, you think somebody's gonna go do something without using AI now? Like why would you go? There might be some creative endeavors in your life, some artistic endeavors where you maybe you don't want AI involved. If you're doing business, why would you not be leveraging AI for everything at all times? Now I am sick of the em dashes. I don't need to see all these em dashes all over the place. But otherwise you'll get over it. That's pretty useful.
Lee Levitt: Yeah, you'll get over it. They're everywhere. You'll get over it. Yeah. The em dash needs a good PR campaign right now. It's gotten a lot of negative press.
Drew Sechrist: I agree. I agree.
Lee Levitt: I'll have Gemini write something up.
Drew Sechrist: Exactly. This is the classic em dash. This isn't known, approved.
Lee Levitt: I actually asked ChatGPT to comment on a podcast episode, which by the way, I used ChatGPT to write the show notes and I said, Hey, Chat, what do you think of this show? Which was all about AI agents, and it gave me a pretty balanced response. It was very interesting. So they're taking over. At some point, we're just gonna hand them the keys to the car and the house and everything else, so we're done.
Drew Sechrist: Skynet.
Lee Levitt: We'll just be passed around by the AIs.
Drew Sechrist: Let's just hope we make the AI so that it's a very nice master of us pets.
Lee Levitt: So it's interesting. I was thinking as you were talking about return to office from a selling standpoint, particularly in enterprise sales, it's really difficult to build rapport. It's really difficult to build trust over a Google Meet and early on not turning on your camera was a disqualifier. Now everyone does, almost everyone does. You can't really build trust over a long distance feed. What's the metric? There's a number above which you can't close a deal if you haven't broken bread. It's like 1.2 [million]. This has been studied over and over.
Drew Sechrist: But if you were doing a $5 million deal, you will have had dinner with these people, right? No question.
Lee Levitt: Yeah. And then that number's probably gone up over time during COVID, I've probably changed, but there is merit to this concept for sure.
Drew Sechrist: Yeah. There's some other standard tests of, is the economic buyer texting back?
Lee Levitt: Yes.
Drew Sechrist: If they're not texting back, there's no deal.
Lee Levitt: Yeah. And if your communication's not via text at a certain point, that's an indicator that you're not really there with that person. So you start out on email or LinkedIn, then you move up to email, then you move up to text or WhatsApp. And so there's the building of trust, there's the tribal knowledge and the sharing, the learning from folks at about the same time you started at Salesforce. I did some work with a services firm and I said to the CEO, so do you want me in the office full-time? And he said, absolutely. And I said, why? I had a different lifestyle in mind. And he said, because it's the hallway conversations that matter.
Drew Sechrist: Yeah.
Lee Levitt: He said it's the impromptu meetings between the meetings where all the work actually gets done. He was spot on.
Drew Sechrist: I dunno if you read the book on the biography of Steve Jobs, but a lot of his design of the Apple office space was really intentional to get people from different parts of the organization to have to walk past each other and see each other in the hallways so that those conversations could happen. It's so true. That was the story of my decade at Salesforce that happened all the time and it just made everything happen faster and spurred a bunch of new ideas into existence and yeah, I'm a believer. There are a ton of tools for sellers to use now, but there's this like fundamental thing that needs to happen in sales and selling and it's this relationship building and there's nothing that really does that. There's no tool for that. I and I also think that there are two things here. One is there's so many tools now. Holy moly. So many tools and it's crazy. People can vibe code a new tool that could be quite useful, but there it is. It's another tool. And that yet another tool. Like we had too many tools five years ago, maybe 15 years ago. We didn't have too many tools. Maybe we were like, oh, I need a tool. Let me go see what kind of tool I can go find. Now everybody's: please no more tools.
Lee Levitt: 10 years ago, the map of the sales stack had over a thousand brands in it, so it hasn't gotten any smaller yet. So it's great Drew all these tools, it can make all of us wicked smart. They can prepare us for any conversation, but who do we talk to? How do we know the person to talk to?
Drew Sechrist: There are tools for that. There are tools that'll tell you like, here's our total addressable market. Here's our scored list of accounts, and here's our ICP and the personas that we wanna get to. And then you can basically click a button and be like, these are all the 47,000 people that you should talk to. I think the real question is how do you talk to them? Why would they wanna talk to you? Because everybody else in the world's trying to talk to 'em too or there, or lots of other people are trying to talk to them too. In sales, who you know matters an awful lot and when you start out in sales early in your career, you don't really know anybody. Typically. Now something's changed. Like I definitely worked with some people early on in my career because of their family relationships. They knew people, they did have some relationships and it is interesting now seeing I'm old enough that like my friend's kids are now coming into the workforce and they're doing the jobs that we were doing early in our career. They actually do have a pretty good network because their moms and dads and aunts and uncles and whatever had these jobs and they have networks and they're like, it's relevant. It's super relevant now, but who you know does matter an awful lot because that can get you a meeting and it can get you goodwill. Which can ultimately get you deals, get you transactions, which gets you more relationships, which gets you more network, which gets you more goodwill to leverage. And so it is like a, there is a snowball effect here over a...
Lee Levitt: virtuous circle.
Drew Sechrist: As you do good things in your career and you help the people, you make promises and you deliver on those promises, then you build up a lot of social capital that you can leverage. So this is one of the most important things in sales, and it was one of the most important things for me. I knew nobody west of the Mississippi when I moved to San Francisco in 1999. Nobody. I was hired by Mark Benioff and the Salesforce team, and so immediately I had this kind of work family that all wanted to see me succeed because my success was their success.
Lee Levitt: Their network became your network.
Drew Sechrist: Bingo. That's it. Their network became my network immediately overnight. Like that I went from knowing nobody west of the Mississippi to having a pretty darn good network west of the Mississippi.
Lee Levitt: Yeah.
Drew Sechrist: I figured that out that this is gonna be probably a difference maker between my success or failure, whether I could figure out how to leverage it. So I figured out how to leverage it. And I think also going back to the earlier comment about like return to office and virtual work. I think if you're early in your career and you don't have those, you're not in the office and you're not developing those personal relationships in person, it's really hard to crack in and leverage those relationships. You just, you don't have the same level of trust. You don't have the hallway conversations to think for things to pop up and talk about it. However, what you can have now is technology that can help you collectively as a company see your entire network and have a heat map of all the relations, the strongest relationships that you can leverage collectively, so that you can even have junior sellers who could have visibility to your board member having a strong relationship with the CFO at the company that you wanna sell to, and then you can make intelligent asks of your board members so that you're not wasting that opportunity. You can get directly to the CFO of that company.
Lee Levitt: Just one Kevin Bacon away.
Drew Sechrist: Exactly. Exactly. You don't have to use all six degrees. You just two degrees and you're there. So there is technology that allows you to do that today. The one that everybody has thought of up until now for the most part is LinkedIn. And you look at LinkedIn and you see who knows who. It's good. I think we're all really happy that LinkedIn exists, but then there's something that's better for this specific use case and that's called Connect the Dots. That's a product that our company has built. I think it's really important to be able to leverage your network. There's a downside. If you don't have the personal relationships with the people that you're gonna be leveraging to make those introductions, you need those personal relationships, so they're gonna feel less inclined to help you out. But there is also technology now that makes it easier for you to do this collectively as an organization. So goes back to is it harder or easier? It's harder and it's easier now.
Lee Levitt: So you can get the map of who knows who and then it's up to the individual to actually put it into gear and use it in a powerful way. And I think about this, if I go to a networking event and I go up to everyone and say, you got something for me? You got something for me? Are you buying yet? That's not networking. That's just shitty selling in a space that's supposed to be non-selling.
Drew Sechrist: Yeah.
Lee Levitt: When you go to a networking event, the correct question is, what are you up to and what can I do for you? Because it's a matter of either making a deposit in the relationship bank account or making a withdrawal. There's a book that I read recently The Third Door, and his perspective is it's not who you know, it's who knows you and what are they saying about you. And I think that's, it's complimentary to what we just described because Charlie, the CFO at XYZ company may not know me, so he is not saying anything about me, but my neighbor plays golf with him, and so I can get an introduction to him, but I have to shape that so that it's a warm introduction and it's accepted and seen as valuable. You do, that's your responsibility.
Drew Sechrist: So even with the technology, it's our responsibility to use it for good. Are you finding that to be true? Oh yeah, absolutely. First thing is, can you see the relationships that are available to you, number one. That's the most important thing because if you can't see them, then you'll never leverage them, right? Number two is then can you leverage 'em effectively? I agree with you, Leah, that like you gotta pay into the bank so much more than you can withdraw so much more. It might be like 99 to one. It might be something like that in life. I'm no saint. I'm a nice person. I'm a nice person. I think my mom will confirm that.
Lee Levitt: You're a good guy, Drew.
Drew Sechrist: Yeah, that's what my mom says. Some point along the way, I read The Tipping Point a long time ago, back in probably, I don't know, I'm not sure that was written in the nineties or two thousands, but it was early in my career at Salesforce. I read it.
Lee Levitt: Yeah. And I was like, I get this a lot. Yeah. So I get a... I understand this a lot. I understand all the personas. I saw Gladwell present on it not long after he wrote it. Yeah.
Drew Sechrist: I'd love to see him talk about it. I think he's written his follow up to it as well, which I gotta go look in into it. So there's a concept of a connector. That's the one who's putting her, "Oh, hey Lee, you should talk to So-and-so 'cause you're gonna go to Croatia that's sailing this summer. And they just came back from a trip and they had a great time and they knew the best captain. And then all the restaurants on which island you should go to and that kind of stuff." And that stuff for me is really natural. And I think for...
Lee Levitt: Yeah, loose. You're a loose connector.
Drew Sechrist: I love doing that. It gives me... I get paid in dopamine hits when I'm like, oh, I'm gonna connect these two people and they're gonna be happy that they know each other and something good came from it. I have some friends, some of them are dear friends who try to monetize on too many different relationships. Like they're like omnidirectional monetizers. I don't want to be that way personally. I'm a monodirectional monetizer. It's like it represented Salesforce for a long time and I was like, Hey, that's my thing, everything else is free. I'm gonna help you with everything else in the world. If you want Salesforce, you gotta pay for it, and you should, 'cause it's a great product.
Lee Levitt: That wasn't your role, that was Mark's role. It was company policy. No free cloud.
Drew Sechrist: He forced us to make people pay for it. Yeah, he really did. I think you live a life of giving back to people and trying to open doors where you can, but also doing it judiciously. That's, this is a really important part. Don't just try to open every door for everybody, because a lot of people wanna get to a lot of people and you gotta, you have to have a bar. And the number one filter is if I introduce somebody to you, Lee, it's gonna be because I think you're gonna benefit from it. Like it's you.
Lee Levitt: Is it a deposit or an actual withdrawal?
Drew Sechrist: Yeah. Yeah. And I care about you primarily. Yeah. You like, who am I making the introduction to? Is that gonna be... And so a good friend of mine says, "Hey, can you get me to Lee?" And I think that the reason that they wanna get to you is not something that you would find valuable. I'll say no, and I might coach 'em. Like, "Hey, I don't think Lee's gonna be interested in that, maybe Lee would be interested in this. Is that something you wanna do?" Or so I think that's the number one thing. If I as a connector am gonna leverage work... if I'm going to leverage my relationship capital with Lee, then it's gotta be in Lee's best interest.
Lee Levitt: Because otherwise your connection dries up.
Drew Sechrist: Exactly. You're gonna stop taking my calls. 'cause if I, "Hey Lee, here are five people you should talk to today," none of which have anything valuable for you. They're just gonna eat your time up. You're gonna be like, put me on the block caller list, or whatever. Yeah.
Lee Levitt: So it's interesting the more we talk about technology, the more we realize there are social issues, there are relationship issues, there are moral issues potentially that come up of how do we use this to, at some level, the purpose of selling is not selling. The purpose of selling ultimately is actually buying, and in fact, it's not even buying. The purpose of selling is to create better outcomes for the customer.
Drew Sechrist: Solve a problem that somebody's got, whether or not they necessarily know it, right?
Lee Levitt: Yeah. Some problems are latent, some problems aren't surfaced until a knowledgeable salesperson says, you could solve that problem by doing this.
Drew Sechrist: Yep. We didn't even know we had that problem, but now we need to move fast.
Lee Levitt: Early in my career, the first book I think that I read on like professional selling, B2B selling. When I got to Salesforce, I think it was the first one, it was Solution Selling.
Drew Sechrist: Yep.
Lee Levitt: And solution selling, just basically all about being a consultant. And I loved it. It was like that was my thing. I wanted to go in and see how your sales process was not good. Where is it not, where's it inefficient? Where are you doing things wrong? And it was so fun for me to diagnose the problem and then prescribe the solution and the solution back then invariably involved Salesforce. 'cause Salesforce was just, it really did, it really, it was an honest sale because everybody needed it.
Drew Sechrist: Everybody needed it. And it was so simple to turn on and it could configure it to your sales process. It was like a messianic fervor that we had. We're gonna solve your problems. We know we can solve your problems. And most people were in agreement with that. Most sales leaders and other company leaders we're in full agreement. We need to get a handle on all the information that's fallen on the floor that our salespeople are picking up and or I have no visibility. I have no predictability. I have no repeatability.
Drew Sechrist: Bingo. Basically, that's the only way I operate. To be honest. I'm a binary seller. I'm not a... I know a lot of people out there who are very good and they can probably sell ice to Eskimos. I'm like, I don't think Eskimos need ice. I don't see that. I can't do it.
Lee Levitt: Yeah, it might be an interesting test, like sell me this pen, but they really don't really need it. It's not a problem they've got.
Drew Sechrist: I'm not good at that. That's not my thing. My thing is like I'm, I get super fired up if I'm like... that's a cool problem and I know how we can solve that thing. Yeah, and we did that for, we did that for a long time at Salesforce. Really, Salesforce was so fun to [sell] because there were so many companies out there that really had problems that we could just come in and we can clean that up, and we're gonna make that so smooth and efficient. That's the kind of problem I like, juicy problem where you can definitely solve it and go in and be a consultant.
Lee Levitt: Drew, I'll tell you a funny story. Earlier in my career, I had some spare time, as in I was between jobs. So I joined LL Bean to open up a company store in Mashpee on Cape Cod, about 10 minutes from where I live now, 17 minutes to be technical, and they shipped the store in on pallets. We built it, and then I spent about four months on the floor in the shoe department, and I'd always said, I can sell almost anything, but one thing I could never sell is something I'm not interested in. And that's shoes. And I find myself in the shoe department at LL Bean, and I loved it. Never brought work home. Customers never called saying their implementation didn't work or the contract had to be blah, blah, blah. But the other thing was, yeah, I wasn't selling shoes, I was selling an experience. Someone would come in and say, I need wool socks and some hiking boots. Sure. Where you going? Finland, November. Have you thought about a base layer? No. It's a base layer. And $3,000 later these people would be happy as clams. Yeah. Because now they knew that their experience in Finland in November was taken care of. And I, as an hourly employee, I got my $12 an hour. So I was happy too, seriously. But I enjoyed this solution selling experience.
Drew Sechrist: That, by the way, reminds me, there's a completely different approach to who's selling. I just saw, do you know Charles Ral? Remember that guy?
Lee Levitt: Yeah. Yeah, he did On the Road, he did back in the seventies or maybe eighties.
Drew Sechrist: You should look at the greatest shoe salesman in the world. Some guy in... I think he's in Pennsylvania somewhere where I grew up. But this guy is a machine. You should have watched the video on YouTube and compare and contrast with your experience.
Lee Levitt: Old school, I'm sure.
Drew Sechrist: Yeah. He was, he sold like two orders of magnitude more shoes than anybody else. It was like crazy. This guy. Maniac.
Lee Levitt: So Drew, what should our listeners take away from this conversation? We did cover the evolution of sales. We didn't go all the way back to John Patterson at National Cash Register in the 1880s, but we did go quite a way back. The history is interesting because some things have changed, right? The technology available has changed and some things haven't. It's still trust building and relationship building and figuring out who to talk to and how to efficiently get there. And I'll say it. Taking care of people.
Drew Sechrist: So I think about, and we've been dancing around this topic or idea, but AI is coming to eat the world. It's automating everything. You're asking like, what's harder, what's easier? What's easier is like all the things that you used have to do manually that are just being tick tick, tick. They're just being eliminated by automation now. Gotta be careful 'cause like they're gonna eliminate a lot of jobs. There's just no two ways about it. There really are. So what's left for you? And I do think that it really comes down to think about what it means to be human and what for the foreseeable future, AI will not be able to replicate. And that is gonna be trusted human relationships. And it could be existing trusted human relationships. It could be new trust relationships that you know that you haven't created them yet, but you're going to. But I think that is one of the most critical things, and trust is the word Trust capital T. There's a lot that goes into it. It's do I trust your intentions? Do I trust your abilities, your competence? Do I trust your follow through? Do I trust all these different things? And so I think you as a human, if you're in go-to market, you're probably the number one thing that you should really be focused on is being a trusted person to all those people in your network that and that you don't know yet. That's gonna be your value. And I think that's good. I think that's great. 'cause you know the world's gonna be very efficient. And then the things that we are uniquely good at doing, building relationships, trusted relationships, and delivering in every way. I think that's where you should focus your effort and go to market right now.
Lee Levitt: I think you're right: in chaos, there's opportunity, right? When a lot of people don't see the path moving forward. There's opportunity to drive forward where technology provides opportunity. There's opportunity to turbocharge relationships, turbocharge connections, and y'all are doing that at Connect the Dots. Drew, where can people find you?
Drew Sechrist: I'm on LinkedIn. You can look up Drew Sechrist. You can also hit me up at drew@ctd.ai. That's my email address and sometimes I'm in San Francisco or Miami or Belgrade, so maybe you'll see me in the street.
Lee Levitt: What's the ideal profile of customer for Connect the Dots?
Drew Sechrist: There are two, so the one that we don't talk about a lot 'cause we don't monetize on it yet, but here's your secret little invite is individuals who wanna manage their networks really well. You can set up a free Connect the Dots account and think of it like... it's like a LinkedIn account except that imagine if it reversed engineered your network by snaring up all of your historical email communications with people. But if you could build a graph automatically just by clicking a button from that's what Connect the Dots does and it's really cool and it's free. For life. The other one is our primary where we monetize is we sell to companies that have B2B sales teams so that they can do that collectively. They can look across their entire organization, see that your board member has a strong relationship with an investor who's got a strong relationship with the CFO that you wanna sell to. So never cold call again, never cold email again, just to activate your network. Where you've got these laser targeted paths to get into. If you're in a B2B organization and you wanna be able to activate that across the entire company, then that's our ICP, but that's who we primarily sell to.
Lee Levitt: So thank you for that. Who's the typical heavy user? In the corporate world, is it the field rep? Is it the inside sales person working on behalf of the field rep? Is it some combination of those?
Drew Sechrist: The ones who know how to use this the best tend to be your most senior sellers. Like your strategic or enterprise account executives. They're the ones who they know how to leverage relationships. They know how to leverage their executives and their board and their customers and their family and their friends in a way that makes sense. 'cause there's a lot of nuance to activating that relationship. The ones that are... there's a lot of potential there, but you gotta be careful is like your SDRs who are early and they're afraid to ask the board and they probably should be afraid 'cause they're gonna annoy the board if they ask for bad stuff. But there's a lot of potential there because they can see across all of the accounts that they wanna get to all of these great relationship paths that they could activate. We actually make that easier for them to not screw up. So we have approval rules built into Connect the Dots. So an SDR can say, I would like us to be able to get to the CFO via our board member, but the SDR can't ask the board member directly. It would have to go up to the chief of staff or maybe the CEO before the CEO approves asking the board member to ask their investor friend to get the introduction to the CFO at that target company. And then, not surprisingly, we're automating a lot of this so that the SDR doesn't have to even initiate this. The act actually just the AI brain will initiate it and say, okay, hey, chief of staff or CEO, you should leverage your board member for this introduction. And then when the AI is good enough at this, then the chief of staff or the CEO won't even have to approve it anymore. 'cause they'll just know that it's got all the nuance down. It knows when to ask and when not to ask. It knows how to ask, it knows who to ask. All of those things. That is the future.
Lee Levitt: That's very cool. Welcome to the future.
Drew Sechrist: Yeah.
Lee Levitt: Drew, this has been a fabulous conversation. We should do this again soon. Check back in two weeks and see how much has changed.
Drew Sechrist: Yeah, a lot for sure will have changed. Lee, it was a lot of fun. Thanks a lot. This was a great conversation with you.
Lee Levitt: Thanks, Drew. Likewise. Another deep dive into the topic of sales excellence and the performance mindset. If you found this conversation interesting, I would appreciate it if you would share the podcast with a coworker or two and to explore this topic in more depth, send me a note by the contact form on podcast.thoughtsonselling.com or find some time for us to talk at https://www.google.com/search?q=meet.acceleragroup.com. Thanks.
CEO, Co-founder
Meet Drew Sechrist — CEO & Co-Founder, Connect The Dots (ctd.ai)
Drew Sechrist is a seasoned sales leader and startup founder who’s built a remarkable career by unlocking the power of personal and professional networks. Today, as CEO and co‑founder of Connect The Dots (ctd.ai), he’s on a mission to transform how teams engage and sell by making network intelligence central to pipeline success.
A Journey from Employee #36 to Billion-Dollar Pioneer
It all began in 1999 when a cold email to Marc Benioff landed Drew an account executive role at Salesforce—as employee number 36. That leap launched him into the heart of an explosive growth curve, where he became the company’s highest-producing seller and later the top-performing sales manager, helping guide Salesforce from zero to over $1 billion in revenue.
By around 2010, Drew had become VP of Salesforce’s High Tech vertical, working with marquee clients such as Apple and EMC.
The Entrepreneurial Chapter: Koozoo, Investing & Advising
In 2010, Drew launched Koozoo, a tech startup that raised a notable $2.5 million in seed funding in late 2012. Post‑Koozoo, he wore several hats—as Chief Revenue Officer, advisor, and investor—helping startups scale and refine their go‑to‑market approaches.
Founding Connect The Dots (CTD.ai)
In 2019, Drew co‑founded Connect The Dots (CTD.ai), a network intelligence platform powered by AI to map and manage enduring professional relationships. The platform’s goal: reduce reliance on cold outreach by empowering teams to lever… Read More