Founders Podcast · 2026-07-07 · 36 min
Key moments - from our scoring
Substance score
58 / 100
Five dimensions, 20 points each
Greg Grant draws on 40 years in sales and fractional CRO experience across 50+ companies to reveal what separates successful enterprise sales from organizational hustle. The core insight: enterprise selling requires systematic process (CRM, compensation structures, territory management) rather than individual heroics. Grant details how to build organizational maps to identify true decision-makers, develop internal champions, and deploy consultative selling - comparing salespeople to doctors who diagnose before prescribing. He discusses how founders can leverage AI for research, meeting prep, and content generation via tools like Claude, while cautioning that AI cannot replace deep strategic thinking or the accumulated pattern recognition from thousands of client interactions. For B2B SaaS founders moving upmarket, Grant outlines the five P's framework (People, Process, Pipeline, Psychology, Performance) and explains why most companies fail due to lack of CRM hygiene, misaligned compensation plans, and targeting too broadly rather than focusing on 25 high-value accounts. The episode tackles whether AI can replace CMOs and sales leaders, with Grant positioning advanced AI as an accelerant for execution rather than strategy.
Map the full organization to identify not just gatekeepers but actual decision-makers and budget owners, then target senior VPs and executives directly rather than staying with initial contacts - Greg navigated Google's entire organization through one champion who introduced him across Fiber, Home, and other divisions.
Salespeople use spreadsheets or Google Docs instead of a CRM, can't prove deal close dates with supporting activity, have high base salaries with no commission, and manage 250+ accounts instead of focusing on 25 high-value ones.
A CRM system for pipeline visibility, defined ideal customer profiles and territories, consultative sales training, clear compensation with commission-based incentives, and deep research on prospects before outreach - all managed through weekly one-on-ones and accountability structures.
AI excels at execution-level tasks (creating videos, graphics, personalized emails, prep materials) but cannot replace 40+ years of pattern recognition, strategic thinking, or consultative problem-solving - it works best as an accelerant for experienced leaders, not a substitute.
A fractional executive or sales consultant for 90 days costs $30 - 50K versus $300 - 400K for a permanent C-suite hire, and can diagnose and overhaul compensation, CRM, and process while training the founder to run sales long-term.
Our reviewer’s read on each dimension, with quotes from the episode.
The episode contains solid practical advice on enterprise sales (organizational mapping, finding champions, consultative selling) and some AI application guidance, but much of it recycles well-known frameworks (ABC selling, doctor's visit analogy, 'what keeps them up at night'). The discussion meanders and repeats points; for example, the importance of CRM and LinkedIn is mentioned multiple times without new specificity. Useful but not densely packed with novel insights.
you want to build what you call a champion
what makes you think it's going to be in July? Well okay, what makes you think it's going to be in July? Like I have my sales teams. Prove it to me
Greg reiterates conventional B2B sales wisdom: consultative selling, relationship-building, ideal customer profiles, and the shift back to 'old school' outreach (handwritten cards, face-to-face meetings). While his AI integration and fractional CRO model show some modern application, the core frameworks (five P's, organizational mapping, ABC) are established industry standards. The positioning as 'old is new' is itself a familiar trope.
Always be closing
you don't go in the doctor's office, shake his hand and he gives you a bottle of bills, right? You sit there for 45 minutes, he asks you questions
Greg has genuine operational credentials: 40 years in sales, successfully closed nine-figure deals at Celestica with Google and Apple, runs a fractional CRO practice with 50+ clients, and has built sales training products. He is a practitioner, not a theorist. However, his current focus is advisory/training rather than hands-on operator status, and the specific dollar amounts and deal details from his major wins are underdisclosed.
at the end of the day, when I closed the $100 million deal at Google, there wasn't much of a climax there
I've helped over 50 clients and I've only had two in the same business
The episode includes some concrete details (11 Labs pricing, Claude Max plan cost $200/month burned in four days, 90-day turnaround guarantee, 90% close rate on referrals) but lacks specificity on the headline claim - the Google and Apple deals are mentioned repeatedly but never detailed (no timeline clarity, revenue figures, deal structure, or concrete lessons learned from them). Most tactical advice stays at the framework level without named companies or detailed case studies.
go to 11 labs. Uh, I think it's like nine bucks a month
200amonth and I burned through it in four days
The host asks reasonable setup questions and creates space for Greg to share, but there is minimal pushback, follow-up on vague claims, or productive disagreement. When Greg mentions closing a $100M deal, the host does not press for specifics. The host allows Greg to redirect or deflect (e.g., 'I don't think I have anything' to the crazy business idea question) without challenging. The conversation is friendly but lacks the rigor of sharp journalism.
Can I, can I ask you a hypothetical question?
So you mentioned you had this million dollar deal with Google
Computed from the transcript - who did the talking, and the words that came up most.
Most founders overlook a crucial secret to rapid growth: mastering enterprise relationship building from the get-go. Imagine closing billion-dollar deals with giants like Google and Apple just months into your startup journey - Greg Grant's story proves it's possible when you understand the real mechanics of B2B sales. Are you ready to unlock the game-changing strategies that can propel your startup to industry leaders in record time?In this episode, Greg shares his extraordinary journey from corporate sales legend to startup founder, revealing how he secured deals worth millions with Google and Apple within his first months. You'll discover why traditional hustle isn't enough - organizational mapping, strategic stakeholder engagement, and consultative selling are the real keys to dominate enterprise markets.
Transcribed and scored by The B2B Podcast Index.
Speaker A: What if you joined a company and in your first month there you closed a B2B deal with Google and in the second month with Apple? This is what we are going to learn today. In today's episode of Founders Podcast, we chat with Greg Grant, the sales expert who made this a, uh, reality. Greg shares his journey of transforming startups into industry giants, revealing insights on enterprise relationship building, cultivate selling and the role of AI in sales. Whether you're a founder looking to gain traction or a sales professional aiming to refine your skills, this episode is packed with valuable lessons. Let's dive in. Hello Greg. How are you doing today?
Speaker B: I'm doing good, Ash. How are you?
Speaker A: I'm good, thank you. Good, thank you, Greg. Before we start then, do you have a favorite quote, something that motivates you, inspires you, you would like to share with our audience?
Speaker B: I think it goes back from an old movie called Glengarry Glen Ross, which is a very famous sales movie here in America, probably worldwide. And uh, the lead character, Alec Baldwin, was going in and joining a team of, uh, real estate agents that were not doing so well and he went and did this whole thing and his thing on the board was ABC Always be closing. So while I've turned into much more of a consultative salesperson as I've grown through my career, it is important. I mean, at the end of the day, if you're in sales, nothing else matters except for your quota and did you hit your numbers or not? All the rest are stories. So I think always in the back of my head when I'm talking, when coaching my sales team is, yeah, that's great. What do you have to do to paint the picture to get to the deal? So always be close. Be the one for me.
Speaker A: Indeed, indeed. And you've been in B2B and B2C, all kind of sales, uh, you know, profiles before. And it would be great to learn from you, especially for our founders who are navigating through the trenches right now. Because I think one of the biggest challenge in founder's life is not building the world class product, but having more people know about it, uh, making sales, understanding how to get more eyeballs. So I think today's episode is going to be very fruitful because this is the thing which the leaders needs to understand, the founders needs to understand to actually gain traction on their product. Right. So Greg, before we jump onto all these details about how you magically make millions of pounds and sorry, millions of dollars because you're in USA for all these, uh, you know, sales, uh, Teams and organizations. Can I, can I ask you a hypothetical question? Can I, can I say let's imagine that you are in a room of, full of founders, right? They're sitting there, they're waiting desperately for, for you to come on the stage. You walk in, the flashlight is on you, you have the mic. What, which story. You will tell them that after listening to it, they will stick with us for the rest of the hour.
Speaker B: Wow, there are just so many through the years. So I guess we have a couple paths we can go down. Um, one would be more of a successful story about sales, but I think more impactful one, especially when the owners, you know, kind of rephrase it a different way I guess in my head is that I think it, at the end of the day, it comes down to your why. And I think what. That's a story that matters. So for me, I would say the story that would be impactful would be my why of, of why I do what I do. Why? I started G Squared Advisors, um, and I had a long career in corporate, very successful, and it, uh, was just time for me to move on. During the career in corporate, I ended up working with a startup, very young CEO, 25 years old and really good guy, really good products, but just did not, uh, have the experience to build a company, build a sales team, anything like that. So I left my corporate job, I got, you, uh, know, a payout because I'd been there for 10 years and I literally took, uh, three months to build it and six months to lead his team for nothing. I didn't even have him pay me just because I wanted to help this kid out. Anyway, when we got to the end of this engagement, which was pro bono because I really just wanted to help this kid, he just looked me in the eye, said, you know what, Greg is from the time you spent me, literally changed my business and you changed my life. And that's where the light went on for me. I've always been in sales my whole life. I went and chased money and done this all kind of thing, but at the end of the day, there was an emptiness there. The money was good, the sales were exciting, even at the sales. At the end, when I closed the $100 million deal at Google, there wasn't much of a climax there. So with what I do now, when I go in and I help these founders that are starting to bring their companies up and help them build out their infrastructure and help out getting their teams accountable and getting them better at consultative selling using AI, I get notes you know, you look on my LinkedIn or my website, there's 15 CEOs that have gushed about what I've done for them and salespeople that have enjoyed working. For me, I think it was that for me it was just really a transition of uh. And I think everybody who starts a business as a founder, there's some something that tickled you that said I have to do this right? If it's just I have to do this to make money, certainly can work, but is it going to be satisfying? And for me as I get older, I want to be around people I like working with. I'm around people that want to grow and be better. Uh, very long story, consent down.
Speaker A: But. Right, so let's get back to. So you mentioned you had this million dollar deal with Google. So you helped scale both Google and Apple at Celestica, right, From greenfield accounts into nine figure revenue relationship. What did you understand about enterprise relationship building that most sales teams still completely miss today?
Speaker B: Well, I think it depends on the level of salesperson. One thing, uh, you know, I think I'm fortunate is there wasn't high tech. There was some very big companies and high tech actually really invests a lot into their salespeople and there's a lot of training. So I was at Celestica, they put me through three different consultative sales training programs because we were, you know, what you call in sales the whale hunters. Right. We weren't going after 10,000 people. So I think the, one of the most important things in enterprise selling is organizational mapping. So what a lot of salespeople do is they go in and they get someone to take a meeting with them and then that's their person. The challenge in most of those cases is that the person that you normally meet the first time is not going to be the final decision maker. They may be able to get you in the room with that person. And so people generally tend to meet one or two people on account and then they try and get the deal done. If you're selling at too low of a level, you're relying on someone who really doesn't understand you or your product, going into executives and trying to sell for you. So, uh, the big game is how do you get in the room with the decision makers and find out what their challenges are and at the same time make what we would. You know, you want to build what you call a champion. You want to get that person that you just for some reason they like you and you like them and it's good. I had that One person at Google. And that was what navigated me through the whole entire organization into Google Fiber and Home and all their internal stuff. But there's one guy. So I think the first thing is go around, find out who that person is. The other thing is, is don't target too low. A lot of people are intimidated to call on a CEO or a senior vp. That's where the good discussions happen. And yes, it's going to be harder to get to them, but if you get them in the room, you're going to have really good discussions and probably move the ball forward in a sale than if you just hang out with one or two people. So I think those are two very important things also. It's going to sound so silly, but don't sell, right? Your job as a salesperson, especially at the highest levels, is I, uh, compare it to a doctor's visit. You don't go in the doctor's office, shake his hand and he gives you a bottle of bills, right? You sit there for 45 minutes, he asks you questions, he pokes, he prods and he says, okay, I think this will help you. That's the job of a salesperson and that's what makes sales rewarding, is you're finding what's. And you don't say this, it's cliche, but we can say it. What keeps them up at night? Right? What are they, two o' clock in the morning? Uh, okay, so let's try and figure out how we can help you solve that. And you can do that. You make money, they solve a problem, and you've got a lifelong friend. That's the magic of real consultative selling.
Speaker A: Indeed, indeed. One thing which I have recognized after, you know, reading through the notes I have is being into sales for a B2C is a totally different game compared to the being in sales of B2B. Because you could sell $10 product to 10 people if you speak with, I don't know, thousand people, let's say minimalistic percentage, right? But you could do it within a month when it comes to B2B sales, you could be engaging with one individual for a year and suddenly you realize that you cannot have a, uh, sales with them because you do not have capability to accept purchase orders or something like that, right? There are so many layers when it comes to B2B serve. Talk to our listeners about what are the prerequisite. Minimalistic prerequisite, especially in software or technology companies, because a lot of our listeners are into tech businesses. What are the very basic prerequisite before even jumping into B2B side of the
Speaker B: business, uh, I think about sales in a, uh, process and systematic way. I'm an electrical engineer by schooling. You know, I'm not the raw lavo agent, so I look at process and systems first. So number one, you have to have a CRM system. You're going to be talking to a lot of different people, you're going to talk a lot of different accounts. They're complicated. You want to have records, you want to have a sales pipeline so you can actually have visibility into your deals and if they're moving forward or if they're stalled and what the next steps are in setting tasks. Those are all the kind of things. Um, I think another thing in B2B sales of course is, and I think in sales in general, which is largely passed up, is doing a lot of research before you have days before you can pick up the call or send that email. Make sure you know about the company and a little bit more about the person. It's amazing the amount of people. Let's see your podcast post. You probably get 20, 30 emails a day from people who want to be in your and 90% of them are form letters. They haven't put any time to put the thought into it.
Speaker A: Right.
Speaker B: When we talked I actually listened to a couple of your podcasts uh, to see if it makes sense. Right. So I think that's, that's really important is to understand and use AI for that for sure. Deep research is a fantastic tool right now. So I think that's important. And I think also you run into this a lot with either founder led sales or the CEO is leading a small sales team just by default. Ah, you gotta do some consultative sales training if you're gonna go in with the approach of I'm gonna sell them, uh, on my cool product. You're gonna lose a lot. I'll tell you that the best presentation that a founder can do is the one they never go in and have discussions, go in lots of open ended questions, understand their business, think about you, uh, know, great opportunity for AI. Hey, I'm going to meet with this client. We're gonna talk about this product. This is where they work, this is what they do, this is what we do. You know, give me three different things that I could talk about from a value proposition standpoint. That or give me five open ended questions. I could ask them to understand more about yc. You can really use AI there to help yourself do the research and prep for the meeting. So I think it's systems now if you have a sales team then it's all about accountability and that's about one on ones and uh, uh, ideal client profile territory. So there's a lot if you were to look at. When I walk into my clients as a fractional chief revenue officer, I've built out a four quadrant 16 spoke model, uh, office. But there's literally 16 different things that need to happen to have a sales organization run a truly. So it's a lot. So read, learn, you know and use a consultant, take some sales training. All those things can help you get there faster.
Speaker A: You also mentioned that in enterprise sales you have to do quite a lot of research, right? And you talk a lot about enterprise sales being treated like a hustle instead of an operating system. What are the clearest sign a company is still running on hustle when it comes to enterprise sales?
Speaker B: So great question. And it's, it's strange because it's, it's blatantly apparent to me. It's almost universal. So when I walk into a client, obviously things aren't good. As a fractional chief revenue officer they've probably hired a couple of VP sales or CROs. It didn't work out. Sales are flattered down. So they bring me in and I see, a lot of times I see the same thing or culture. I see CEOs not trusting sales teams. The biggest thing to the direct question is no system. I walk in and I have this salesperson as a spreadsheet and this person has a Google Doc and this one and I'm going to ask them when are they going to close? Oh, I don't know, sometime in July. Well okay, what makes you think it's going to be in July? Like I have my sales teams. Prove it to me. If you can't prove it to me right then there's no system there. What I also do is I interview all the sales team, CEO, coo, cfo, anybody who will talk to me and understand what they're doing right now. I find crazy things. I find CEOs that they're uh, pay their sales people very large base salaries, no variable commission and they wonder why they're not selling. And to me it's almost common sense. But maybe it's common sense because I've been in sales for 40 years. A salesperson is not going to be motivated to get up and hustle if they don't have something to chase and make more money. So it's a combination of lack of process which uh, I can find out quickly with the system, lack of strategy. Do they even know who they're calling on? Do they have their territories designed? Right? Do they have the right people in the right seats? Execution, how are they doing it? How are they approaching the market? How are they, there's a value proposition, clean. Have they done a uh, SWOT analysis how all those things uh, fit together and then strategy, right? Where are you going from a big picture standpoint? Are you just going out and running? And you don't. So it's, there is a lot of that. Like hey salesperson, here's a list of 250 accounts. Go get them. And I would say take the top 25, throw the rest out and let's focus on those and really try and get something done. There's not a salesperson in the world that can service 250 accounts.
Speaker A: Indeed, indeed. And that, that is a very good uh, you know, flow into my second next question which is imagine you join a new startup, they have an amazing product, best product in the world, right. It's built for an enterprise let's say. I don't know one of the product, um, you, you join a company which has a product which let people automate video editing. They can add captions, they can cut silences, the denoises, everything. So you know the product is really cool because now anybody can just create some API calls or automation with an attend or something like that and then upload a video, RAW video on one end which is Google Drive and the other end it's all polished, edited, everything. Right. Good product. What is the step by step framework? You as a sales director or as a CMO or whichever position or title you think would be responsible to bring more sales in from the B2B spectrum. What framework do you use step by step to make sure that this company becomes a successful B2B entertainment.
Speaker B: So I wish I could give you a clean answer on that. And the reason I can't is that every one of my engagements is custom. There's nobody that's the same. There are certain overarching things I'm going to look at. So if you look at the uh, the sales training programs I have with the, @the aisalesleader.com I run everything off of a principle called the five P's right. Which is based off of people process, pipeline, psychology, like those kind of things. So it's all based under there. So you have to look at all those buckets first. You have to look at all the things I was talking about process, strategy, execution, accountability. But it's, it's it's just literally different. I may go into one client and all their salespeople are doing great on LinkedIn. I may go to another client and their salespeople don't even have a LinkedIn profile. I have a client I'm working with right now and they have account manager team. Account manager team's never had any sales training. So I guess the thing is there are people who do what I do that have what I would call a cookie cutter approach. And this is what we do every time, right? That's not sales to me. Sales to me. Going back to before is understanding your specific challenges and developing a program around that. So the process I have is getting in and get now I will do a scope of work to start and things that will be done will be like CRM system, compensation plans, onboarding, coaching, weekly one on one CRM hygiene, all those type of uh, really important things in an organization. So I have the buckets, but as far as how I approach those buckets, I mean I've been doing this particular business I've had for seven years. I've helped over 50 clients and I've only had two in the same business and every other one of those were in businesses I knew nothing about before I started. So I live a kind of a chaotic life because I have to get in and very quickly understand their business and figure out how to fix it.
Speaker A: What information would you need to anything hypothetical. What information you need to define a framework. The reason I'm asking you this question is because what happens is when our listeners are listening, they want to understand what is your approach towards getting into the mud and making things out of it. Because hiring uh, a C suite executive like one yourself, is very expensive first of all, right? And in order to make that decision, the listeners need to understand if this approach or a framework would work with them or not. So what kind of information would you require in order to help our uh, listeners to define our strategy?
Speaker B: I think the, the question back would be or thing to consider is the size of the company very different if it's a company that's, you know, two people running the company, you know, uh, it's, it's not affordable. So a really good option is what I do. You bring in a fractional executive, it's still not cheap, but it's cheaper if you look at burdened and benefits and all those kind of things and you're bringing in someone who's an expert. So what I can do in 90, I guarantee it and uh, all my clients will Tell you I can go in and completely turn around a sales organization in 90 days. But if they're a bigger company, right. So what's the structure? Do they already have a VP and three sales managers and a sales team? Is it just founder led sales? There's a big difference there of how you approach it. If you can afford it, yeah, of course. Get the bigger person because they're gonna be better at the job. If not, I really do think a fractional executive bringing somebody in for 90 days, that's what we do. We go in and we figure out what is not working and we make it work. So yeah, uh, it's a tough situation. A lot of my clients I've had were under $2 million and that's why they bring me in. Like I can't afford 2, 300, $400,000 for a C level person. But you know, I can spend 30, 40 grand, have a fractional person come in, get me set up, teach me how to do this and then you know, build a, build the Ferrari and give them the keys at the end.
Speaker A: Sure, sure. A lot of people now sort of like prove or I wouldn't say prove. A lot of people communicate on different social media, especially on LinkedIn, that you don't need to sort of hire a CMO anymore because you can actually use AI to completely replace your marketing team. First of all, the marketing mediums have changed drastically in last 20 years, right? We had newspaper, we had television, we had billboards. All that has been shifted to digital world. Now people at least touch seven times a brand before making a purchase decision. People buy from people nowadays, uh, company founders, they are more active on social media. They have special departments for it who generate different kind of content to create trust. Because trust, creating trust is almost very expensive now in a saturated space. I understand that AI is, you cannot run away from AI now, but how much do you think these kind of uh, statements are valid and what are the repetitive or, or not even not repetitive, but even sort of creative aspects of marketing and sales which AI would replace completely in next five to 10 years.
Speaker B: Boy. Yeah, that's a, that's a big discussion point right now. Anybody in marketing that's listening probably won't likely. But I do agree with you that, that, that marketing is uh, a lot of things. Like for instance if we're talking among um, a flyer for the AI sales leader for the programs there, Claude's doing it for me. I would have had to hire somebody on Fiverr or Upwork or something before I wouldn't hire somebody in the US Sorry. Use outsourced labor as well too. So, yeah, I mean, marketing, LinkedIn. I do all my own stuff. My brochures, all my posting, all my blogs. I do it. So I think the doer, kind of the digital agencies, digital designers, graphic designers. There's. I think the area though it's still will be needed. Is that the higher level, the CMO level? That I don't know. I've done a couple marketing plans with AI. They were okay, so I don't know. I think the higher level strategy, but the lower level, you know, hey, I need a. I need to, you know, look, I can go into a number of programs, give it a prompt while I'm talking to you, have it run 30 videos. I come back and pick the top three. And I've got my post for LinkedIn for the week. That's true. And it's written the post for me. So it's a real deal, even for me. Right. So one of the big things I do for my clients is compensation plans. Right. Well, I'm good at it. But there are people now, I think that think that AI can get it done. We're in a period right now because now AI, look, a lot of people still use AI as a chatbot, but the people who are advanced in using it like I am and building agents and all these kind of things, they're seeing those possibilities and even for me. So, okay, yeah, I'm going to do a comp plan. Well, uh, I'm a CEO. I'm going to do a comp plan for my sales team. I'll do three of them and I'll pick one and see how it works. What's going to happen? My prediction, I'm seeing it happen now, six months, they're going to realize that AI cannot, uh, replace someone like me or someone at SE level that really has. I got 40 years on the street. AI has not sat in 3,000 sales meetings. So that kind of thing, I don't think that can be replaced. I don't think the consultative salesperson, I think on the B2C side, you know, their AI business development reps and things like that. It's kind of creepy. So I would say just like in most things, like in here, they're talking, in America, they're talking and bookkeeping, um, things like that. So where I see AI hitting it is at the lower levels, the entry level, the people with, you know, three years experience. My theory, and hopefully I'm right, is that if you dive into AI and you become an orchestrator of these systems use AI. The more you realize that yeah, they can do things, but the deeper and the bigger the projects. Gets confused a lot and you have to retract things. I was working on my website. I could have probably hired somebody to do it for a thousand bucks. But I'm learning it, so it's okay. Anyway, so short story, I think lower skilled people there, there will be risk. The higher end, I don't know for sure, crystal ball, but I believe we'll be okay. Also though, that's why I've diverted too and started going more into the sales training realm. Because I'm seeing what's happening in my core business and what I've done now to counteract that is to develop the a sales leader and have training programs that don't exist today about training salespeople and sales leaders and CEOs how to sell and how to utilize the technology. Exactly how you're talking about to utilize and make yourself a force multiple.
Speaker A: You also trademarked the casl, Cash Reap and the sales leadership firm, right? What gap in the market did you realize nobody else was solving properly when you did that?
Speaker B: So one of the other things I do is I do a lot of sales leadership training. I've been doing this for years. I go in, they have a sales leader, they're new or they're young. I go into, they mentor them. So through this, of doing this, you know, many years, I said, wow, you know what? And I looked. There's really no great sales leadership training programs period out there. There's lots of sales programs, right? How to sell, how to close, how to get motivated. Nothing for sales leaders. And then I said, wait a minute. Not only is there anything for sales leaders, but there's nothing for sales leaders with AI Forward. Some of the older sales training companies are like bolting on a module. Oh, we have an AI roleplay tool. We have this. I built this from the ground up. AI forward. So no sales leadership program. No sales leadership program with AI. So that's when the light bulb went on. So I built that, then I built that and said, well, that's great, but how are the salespeople going to get trained? So then I built cash, which is for the new business development salespeople and reap, which is for your account managers who have to get more business. Then I said, well, being a VP of sales or CRO is really a very lonely place to be. You don't have anybody to talk to. Nobody in your company that you can strategize with. So I'm building a mastermind forum. It's a safe place for 12 sales leaders from different industries to come in virtually and do issue processing. Hey, I've got this issue with my team. Hey, how are you guys using AI to do this? It's cheap, it's online, people from the UK could join as long as I do it early enough so that, that's kind of where the whole thing came from. And plus I'm um, being an engineer, this is the most excited I've been about technology. And you can probably hear it um, pulsing about AI right now because it's just for me it's changed my life. It's been able to productize what I did this. There was bits and pieces of this program for years and I've done these trainings informally. But within a six month period I was able to pull the entire thing together, you know, and that's like 700 PowerPoint slides and websites and videos, all that kind of stuff. Had it not been for AI is probably three to five years before I would have been able to launch it.
Speaker A: Great stuff. So before we move towards our quick fire round, uh, Greg, what I wanted to ask you is a golden nugget. What steps a founder should take. Let's say imagine a small company, right? Couple of million, they have raised 10, 12 people working in the startup. They founded it based in Silicon Valley and they are into B2B space. What steps they should take? Maybe let's say three or four steps to get ready before even approaching to B2B customers. And then once they're ready, what steps, what strategy they should use in order to get B2B sales.
Speaker B: Well, first thing is truly understanding your value proposition. What is the value you're providing? Not your cool product, not the features and benefits, the end result. If I'm on the other, I always tell all my clients and salespeople, sit up, make believe you're on the other side of the desk and somebody's listening to you pitch to them. How does that feel? So do some fake pitches. You can build yourself an AI role play tool. Very easy. There's commercially available products. Here's my big tip for the day. If you want to do it yourself, go to 11 labs. Uh, I think it's like nine bucks a month. They have a little thing called voice agent. You go in there, you write a little script and you can literally role play meeting. Take that need out, run that through your AI, have it do some coaching and some analysis for consultative selling techniques. What are the three things I did good? What are the three things I could do? Test it, play around with it. You have the technology to do that? Value proposition number two, ideal client profile. Who is your ideal client? If you tell me your client, your ideal client is companies with one to 20 people that are under $5 million, I'm going to throw you back and tell you to keep working on it. You need to boil that. Who is not? Um, everybody who could buy it, who is. You could only pick one client. Who is that? Find out who that is, then go out from there, duplicate that. And then you have to think about your outreach. How are you going to do it? There's a combination. I hate to say this so, you know, as a lifelong salesperson, but email prospecting is largely dead right now. If you even get through it. Spammy. Unfortunately, LinkedIn has been my main thing for years and it's getting very AI sloppish now. I mean, uh, transparency. My LinkedIn posts, I edit them, but LinkedIn but AI drafts them for me. It does all my imagery, right? And you see it now if you're smart and you know AI, you can see the poster AI, you can see the comments are AI. A lot of automation going. So it's tough. So it goes to me, back to selling when I started, you know, in the 90s, it's like you gotta go and you gotta meet people where they are and face to face and have coffees and lunches and drinks and dinners and build personal relationships. Right? People buy from people they trust and like, period. You're not gonna buy.
Speaker A: We are going back to 1980s, 1990s.
Speaker B: Exactly right? Man, it's just like the Levi's come around, it's the same thing. What's old? Sending. I have sales team sending handwritten cards. I have them listening to a podcast and the guy said, oh, I really like Jim Jones whiskey. And then they sent him a bottle of whiskey. Like things like that, just to be memorable and different because it is noisier than it's ever been before. Asher.
Speaker A: Indeed, Indeed. Great. So any particular pointers you want to highlight before we move into our quick fire round to the founders after they have done all this? What you have mentioned, any particular strategy? I know email outbound marketing, LinkedIn is very tough to do, but being in AI, anything which have, uh, worked for you in past couple of months or you think might work in the future,
Speaker B: I'll give you the big don't and the big don't. Don't think you're going to send out 10,000 emails and get these clients in B2B. Now this is a whole different uh, thing which can. So B2C, that's all marketing, right? So you can do like. Yeah, I don't know, I don't plan on doing like Instagram and TikTok for what I do for a living. But in that case I think it's frankly I think in B2C it's a lot easier to reach scale because the sales are easier, they're quicker, they're lower dollar, they're easy to make a decision. But your point before sticks with me that uh, you interact with a brand seven times before you make a purchase. Break this up all the time. You go on a website, you put something in your cart, you don't buy it and you get the email once a week and all of a sudden three months later you're putting into the cart. That doesn't happen when you're selling a $250,000 center switch. So it's a very different methodology where you can be more feature benefit product pushy with, you know, buy it today, get 20% up.
Speaker A: Mhm.
Speaker B: If you're selling B2B M, the more complex the sale, the slower you have.
Speaker A: Great stuff. Well, great. Thank you so much. Let's move into our quick fire round. I have got six quickfire, ah question for you at any stage. If you feel you don't want to answer any question, just give me a skip and then I can move on
Speaker B: to the next one.
Speaker A: Sounds good.
Speaker B: Good, let's go.
Speaker A: Great. What are the top three strategies to generate leads in 2026?
Speaker B: Man, that's a bomb, Ash. Uh, let's see. I think I still would say LinkedIn is good. Cold calling. What's old is new and networking I think is number one right now you need to have a referral partner network. My business is 100% referral based. I had luck. Knock on wood or make too much noise on the mic here but uh, you know, it's been seven years, my phone rings every couple months and we're good to go. That's the big thing. Network. Join networking groups, meet people, meet with people that could be clients. Build relationships, ask people for introductions, get involved in the community. It'll take a while to build, but there is no better business than referral business because it closes at an extremely high rate.
Speaker A: Yeah, because you, you, you're basically getting trust passed by from your previous or
Speaker B: friend or customers to that trusted advisor. It' I think my close rate when I'm referred in is probably 90% great stuff.
Speaker A: What book would you recommend to our audience and why?
Speaker B: Okay, that's an easy one. So my favorite sales book is called New Sales Simplified by a guy named Mike Weinberg. A15Amazon fantastic consultative sales training book. Yeah, I like him. And there's another guy named Jeb Blount. J E B B L O U N T. I'm a big fan of his books too. Um, and I'm writing my own now, so about a year away.
Speaker A: Which, which one are you writing? Would you be able to share?
Speaker B: I'm building. I'm writing a book about my strategy and how I go to market and how I use AI with my clients and all the things that are modeled off of the Certified Sales leader training program. So it'll be a big one. I think I'm about halfway through the intro now, so stay tuned.
Speaker A: Uh, perfect. Great. What's one attribute or characteristic in your mind of a successful founder?
Speaker B: I'm sorry I mentioned that one.
Speaker A: What's one attribute or characteristics in your mind of a successful founder?
Speaker B: One is hard. Tenacity.
Speaker A: I agree. I have interviewed more than 200 guests on the show by now and almost, at least if on top of my, you know, uh, head, I think at least 30% of them said tenacity is one characteristic.
Speaker B: No, it just, it happens. When you're an entrepreneur, stuff happens and there's nobody to help you. Real life situation. It was two days ago and I was working on my website with AI and I got a lead introduction about four o'. Clock. Really hot lead, looks like a really good prospect. And the introduction to my referral partner says, take a look at Greg's website. So I go, quick sanity check at the website. Oh my gosh. AI went in there and it did change some imagery and some text. And I know I have a prospect looking at my website and reading now. So it's, uh. And that stuff happens all the time. As an entrepreneur, you run into something, you're like, oh my gosh, what am I going to do? And there's nobody to help you, so. But the upside is you're working for yourself. You can make good money, you can help people. And, you know, I really, I think being an entrepreneur is a wonderful lifestyle. However, when the shit hits the fan, the shit hits the fan.
Speaker A: It does. It does. Is it, uh, what's your favorite personal productivity tool or habit?
Speaker B: AI? Claude.
Speaker A: Yep. Yeah, Claude, are you using the Max plan? I'm guessing yes.
Speaker B: Oh, yeah. 200amonth and I burned through it in four days. I've had many 18 hour sessions with Claude and eating and sleeping became optional and lots of coffee. But, uh, I love it. Again, the engineering side, I'm watching it write code and I'm like, wait a minute. I just told you to do this power presentation in three minutes. It's done. And it's better than anything I ever could have done. Even if I took 20 hours of PowerPoint classes. Close me away every time. I'm amazed and uh, equally frustrated when I ask it to do the same thing 40 times and they still can't complete the task. So this, there's both sides.
Speaker A: What's a new or a crazy business idea you would love to pursue if you had time?
Speaker B: I don't think I have anything. I got two businesses running right now. Ash58. I can't think of anything else. Just right now, this is.
Speaker A: Tell me a gap which you might have recognized in the past, which you would think it would be a good idea. Somebody built something.
Speaker B: Oh, I got it. CEO training for how to work with your sales team. That actually might be a program. I'll write that down. Here's why. Every company I come into is the same thing. I don't know what the salespeople are doing. They're not selling up and they're mean and they're condescending and they don't spend any time with them. You know, it's like one of the things in my book is like I ask every CEO when I start, when's the last time you had lunch with your top salesperson? And every time it's the same thing. They give me a blank stare. Can you believe that you're the guy that's bringing in or woman that's bringing the most revenue for the company? If it wasn't for that person, you wouldn't have finance, you wouldn't have hr, you wouldn't have your people in operations. And you haven't had lunch with him in a year. You don't even know what his kids names are. Ash. It happens every time. It blows me away. That's it. Having to use work. And there's probably a book like it out there, I'm guessing. But like the CEOs that I can't stand are the ones that sit in their office with the door closed. Don't be that guy.
Speaker A: Don't be that guy. What's an interesting or fun fact about you that most people don't know?
Speaker B: Uh, let's see. I was a hang glider pilot for 20 years.
Speaker A: Wow.
Speaker B: And then I guess the other one which always shocks people is I'm very, uh, into hardcore heavy metal is my choice of music. People generally don't look like my look doesn't quite, I guess, uh, stereotypically look like what a hardcore metalhead would be. But if you saw me when I was 16 and had hair around my shoulders, then it would be different. Yeah, those are things that typically people wouldn't guess at a first discussion with me.
Speaker A: I'm picturing already that when your cloth is programming, you're playing some metal in the background and then like vibing through it. Right.
Speaker B: Yeah, you. You pretty much have it knocked out. Ash.
Speaker A: Yeah. Great. Greg, thank you so much for joining me and sharing the story, unpacking, you know, all the wisdom. If people want to get in touch with you, what's the best way to do it?
Speaker B: Sure. Can, uh, certainly reach out to me on LinkedIn. Just Greg Graham. G R E G G R A N D um, and then definitely go check out the AI sales leader. V T H E V A I Sales leader, which will go into great detail on all of the sales training and coaching.
Speaker A: Perfect. And you also mentioned that you have a freebie for our listeners if they want. So what would you that be?
Speaker B: I do, uh, I have a couple different things I'm thinking. I'm. I'm writing a couple of different articles right now. I'm finalizing. So I'm going to kind of take our discussion of what we had today and either modify one of those or probably just write something fresh that'll be pertinent to our conversation. Matter of fact, if you happen to have a transcript on this, that would be cool to send to me and I could start getting some ideas. But yeah, I'll get something and give it to you so you can send it to your viewers afterwards.
Speaker A: Great stuff. Well, if you're listening to this episode, sign up to our newsletter. And you know, obviously you get new episode and founder story straight to the inbox, but you will also get a direct download link from Greg with the freebie on your way. Right, Greg, thank you so much for joining us today and sharing your inspiring journey and the impactful work you're doing through your educational services and coaching services. It's been an absolute pleasure having you on founders.
Speaker B: Thank you, Asha. Thanks for having me. It was fun.
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