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Episode

Jeff Lerner on Why 70% of Founders Change Their Product Before Launch

With Jeff Lerner/June 16, 2026/48:40 listen/Hosted by Jordan Lally

Jeff Lerner is a fractional CMO who works with startups and small businesses on positioning and go-to-market strategy. He has helped startups raise $425 million and been part of four exits worth $2.5 billion, with earlier career stops at Google and AT&T. His current practice is built entirely on referrals and word of mouth, which he describes as both a point of pride and his single greatest source of anxiety.

The conversation covers how Jeff approaches a new engagement, starting with questions rather than a preset playbook. He estimates that roughly 70% of the founders he works with end up making some change to their product before it goes to market, the result of working through repeated why questions that shift attention from feature sets to the actual reason a buyer would pay for something. He also walks through the free brand assessment tool on his website, explaining why giving detailed analysis away is both a genuine service and a lead generation strategy.

Jeff is candid about the parts of his business that do not work as well. A LinkedIn outreach campaign he ran last year produced calls that were either far outside his price range, asking for equity-only arrangements, or, most commonly, founders pitching him their own lead generation services. He also addresses the word fractional directly, arguing that it should describe a fraction of time and cost, not a fraction of value or strategic involvement.


What You Will Take Away


About the Guest

Fractional CMO
Jeff Lerner

Jeff Lerner is a fractional CMO with 25 years of experience, including time at Google and AT&T, followed by a decade working exclusively with startups. He has helped founders raise $425 million and been part of four exits valued at $2.5 billion. His practice focuses on brand positioning and go-to-market strategy for B2B tech, SaaS, logistics, and supply chain companies, as well as B2C businesses competing in crowded markets.


In This Episode


Full Transcript

Full transcript of the conversation, published verbatim. Speaker labels come from the recording itself, not from an automated guess.

0:00 · – Introduction: Meet Jeff Lerner

Jordan:0:00
Welcome back to the [High Ticket AI Systems] podcast. Everyone please welcome the one and only Mr. Jeff Lerner. Jeff, how you doing today, my friend?

Jeff Lerner:0:08
I'm doing well, Jordan. How about you?

Jordan:0:10
Fantastic my friend. Happy to be here. Let's see. First question we always ask every guest is what's your offer and who is it for? Basically what do you sell and who is it for?

0:23 · – What a fractional CMO does and who it's for

Jeff Lerner:0:23
Yeah, so I'm a fractional CMO for startups and small businesses. know, those organizations that are either, I've seen and experienced some growth and some level of success and have hit a wall and are looking to kind of get past that, or organizations that are relatively new and have a great product or a service that they're bringing to market, but don't necessarily have the brand to kind of back up and partner with their product.

So I come in, work with them, help them with their positioning and go to market strategies and hopefully help them raise a lot of money, exit, get acquired, all those good things.

Jordan:1:04
No, I love it. Let's see. In regards to clients that you currently work with, I know it might span pretty widely, but what are some industries you're currently working in?

1:13 · – The industries Jeff works in: B2B, SaaS, logistics, and more

Jeff Lerner:1:13
Yeah, I tend to have a lot in the B2B space, specifically tech and SaaS and some of those different solutions. I've also had a lot of logistics and supply chain clients over the years because I had a role in that industry for a couple of years. And so I understand it and speak the language. And so I do work in that category a bit. And then on the B2C front, I do get some clients that come to me that are looking to bring to market their products, and especially in very saturated markets where there's a lot of competition, they come to me to help me overcome some of those challenges of how they can differentiate and stand out amongst the competition.

2:00 · – If Jeff joined your business today, what happens first

Jordan:2:00
For sure. Thanks for the context. Most of the audience are B2B operators, so I'm going to ask some questions on that side. So imagine you and I just partnered up. I'm going to bring you on as a fractional CMO. What are some immediate things you're going to take a look at and do to have the business grow?

Jeff Lerner:2:17
The first thing I do, honestly, is listen and ask a lot of questions. You're not bringing me in as someone who's just going to show up with my playbook of what to execute. My playbook comes from what I'm hearing from the founder, from the leadership team, the questions that I'm asking. It can get cumbersome from founders because I'm constantly poking holes at You know, things they say or things that the sales team or others in the organization may be talking about. But the goal of that really is to pull out the narrative, pull out the way in which the organization is going to market. And once I have that foundation in place, then I can help craft the outgoing messaging, you know, what the strategy needs to look like, how to bring cohesion among all the different groups. and stakeholders within the organization to make sure they're telling the same story. So it is a lot of questions. It's a lot of time to just discuss the business and the ultimate goals that they're looking to achieve.

Jordan:3:24
Gotcha. When it comes to, let's pretend for a second, you understand the narrative, my goal, I want more clients, I want to scale responsibly, right? Do you have any avenues, strategies, marketing frameworks you would want to implement into my business to help me grow? And I'm using my business just as the example.

3:46 · – The AI assessment tool he built to diagnose your positioning

Jeff Lerner:3:46
Yeah, you know, it's a great question. mean, it really, every company is going to have their own unique approach that I'm going to take to it. But I'm going to look at the business. In this case, I'm going to look at your business. I'm going to do an assessment. So I have tools that I've built, AI tools that will do an assessment in partnership with the inputs that I give it to really help understand your positioning, where you are in your go-to-market. how you're differentiated or not differentiated. And then I'm gonna be building a plan that says, hey, look, here's what you got going on, here's what's going well. And here are some of those opportunities that we really need to dive into and focus on. And once we focus on some of the internal implementation, then now it's, here's how we can bring that to market. Here's what your messaging should be to reinforce to your audience, to your ICP. where you do add value and what you can bring to them in terms of a solution. So it's both the internal side of how do we do it and what do we need to build or say to create that, but then the external of how do we then tell the audience we want to hear it, how do we tell them that message and get them to take the action that we want.

5:05 · – Why founders pitch features instead of outcomes (and why it kills sales)

Jordan:5:05
think that's my favorite thing internally in my business, always refining my messaging and my offer. And also on behalf of clients as well. Like earlier today, I had a working session with the client. It like an hour and a half call. And that's all we did because they have this new product that they want to bring to market. And it was just very fun for me from a business owner's strategist standpoint on honing in the messaging, really dialing in the offer. coming up with different creatives that we can utilize. was really fun for me. I imagine you enjoy that process as well.

5:36 · – The "why" question that changes everything for founders

Jeff Lerner:5:36
I do, you know, it's especially when I'm working with founders who don't have a marketing background, which is a lot of them. You know, they start off when I asked them to tell me about their business, their product, their solution. They're giving me feature sets and telling me all of the cool things that their product can do. And that's great, but that's not the reason why someone's going to want to buy it or use it.

And so I ask a lot of why questions. So when they say, well, we can do X, Y, and Z. Well, why is that important? You know, our product will allow you to, you know, tackle these three tasks that, you know, our typical audience might have on their plate. My response, why is that important? Why would someone want to buy this versus something else? You know, why did you even build this in the first place? And so there's a lot of that that gets pulled out. because founders are usually great at thinking about their product and what they want it to do. They don't always think about the how it's actually gonna land and why someone would actually want to use it or buy

Jordan:6:50
That is so, so, so great, great point, my friend. And as you're articulating yourself there about getting to the root of everything, I kind of had like a moment in time where I was like early, early, early college days. I was like, I don't know, 19, 19 years old. And I kind of had that same approach about. life and like philosophy about life. Like why do we do things? Okay, like after we have that answer, ask why again? And you bring it to the marketing and business forefront. And I think it's very, very applicable. And sometimes, maybe from your own experience, maybe from my experience, but when you are asking these founders the why question, and like the fifth one, they kind of get stumped. They're like, why am I actually doing it this way?

Why am I trying to solve this problem? And if you can really extract that data from them, it kind of shifts their perspective, shifts their lens. But you can't tell someone from a dictatorship approach saying, change it. Change it to this way because I already know the market is going to want this. You have to ask them why. So very, very high five to you.

7:57 · – Why 70% of founders need to tweak their product before it goes to market

Jeff Lerner:7:57
You know, and the number of times I've worked with a founder who has, as we go through this process and I ask those questions that we ultimately make a change to the product in some way before it goes live or very early on, it is probably 70 % of the time. And it's because they didn't think of it from that perspective of the why someone would buy it. So there are times where it's. you know, as I'm asking those questions and they have the epiphany of, yeah, okay. Like, why would someone buy this? Well, they would buy it if it could really help them do X, and Z. We had actually built this to do ABC. They're very similar. We need to make a slight tweak to some of what we're doing here because then it actually solves the issue and the need, not just is promoting what it is that, you know, the capabilities of the product or the tool.

And so those are the conversations I love the most when there are those aha moments of, okay, we need to make some sort of minor pivot or adjustment so that we really do have a product or a solution that will be valued by our target audience and they would want to engage or buy.

9:16 · – How fractional CMO pricing actually works ($5K–$25K/month)

Jordan:9:16
I love that. I freaking love that, my friend. Fractional CMOs are so interesting. Don't go into specifics. Please don't. But from a pricing model, how does that, how do you typically work?

Jeff Lerner:9:28
Yeah. So, I mean, I have pricing on my website, right? Like, it's, and it's because people come and, and, you know, they, they want to know, you know, I'm a business of one. So, you know, my pricing model is you're hiring me. and I'm very clear that I'm not a marketing agency. You know, I am not, when I land a client, I'm not going out and hiring a junior level person to really come service it while I just kind of sit here making money off of it and not really doing anything. that that's not my approach. So I take only a select, you know, number of clients at any given time. And depending on the scope really determines what that pricing looks like. So what, if it's a, you know, sometimes a client is, you know, look, we need a full time. They don't want to hire a full time CMO, but they really want someone full time for three to six months as they're going through. a big strategic change as they're trying to raise around the financing. And so that has a much different price tag to it than a startup that says, look, we don't need full time anything at this stage. We want 10 hours of your time any given week. And so these engagements can range from five to 7,000 a month, anywhere up to 25,000 a month, all depending on what the actual know, scope of work looks like and what we decide makes the most sense for those organizations. Yeah.

10:59 · – Why he left corporate life and became fractional

Jordan:10:59
Thanks for being so transparent. When, what led you to shift into being a fractional CMO? If you don't mind me asking.

11:10 · – The hard truth about company loyalty and why it's a lie

Jeff Lerner:11:10
It's so cliche when they talk about variety is the spice of life. And I almost want to punch myself for saying that right here on this podcast. But when I look at it and I realize that I've been part of organizations, I've been part of organizations where I've stayed for a long time. And you you. learn a few things as you go through and as you get older. you know, obviously one of the big life lessons is, you know, organizations always ask for loyalty, but they don't give it back. And I find that to be so utterly frustrating. I've been through it. I have friends that have been through it where you give your blood, sweat and tears for years. to a company only to wake up one day and they're just like, hey, we decided to go in a different direction. And that's a gut punch for so many reasons, but it also is the proof, right? That you are disposable, of course, as you should be, right? Like every employee, you know, that's what working and having a job and all that stuff is all about. And so I kind of wanted to get away from that.

And at the same time, going back to that variety is I've learned so much because I have an opportunity to work with so many different clients. I've had an opportunity to work in healthcare. I've had an opportunity to work with organizations in FinTech. I have an opportunity to work with private equity firms. And so I'm getting all of this exposure to the way in which business is actually getting done. across so many verticals and learning so many new things that I never would get if I was solely focused on one business and one business alone.

13:05 · – How Jeff gets clients: referrals, word of mouth, and nothing else

Jordan:13:05
Amazing insights. How do you currently attract clients for the company? Because you work in many different, not work in, but you understand the question. I'll shut up.

13:15 · – The anxiety he carries every day about where the next client comes from

Jeff Lerner:13:15
Yeah, you know, I've been really fortunate that, you know, kind of all of my business, you know, has been through referral and word of mouth and introductions that people have made. You know, I like to say like, you know, my work is the marketing. So by producing good work and having, you know, great clients who refer me to others, you know, that continues to be really, really beneficial. And obviously I'm so appreciative of what that You know has looked like for me at the same time. It is also the thing that keeps me up at night because you never know when the well dries up or you know or something happens and so I'm you know sit here and be like well, I don't really have the robust pipeline of you know new business that I could just you know add something new to my portfolio, you know tomorrow if I needed to so But as they always say, like I, a marketer, I am the worst marketer of myself and what I do, you know, it's both a combination of like humility and like, don't like openly love to just talk about like, Hey, look how great I am at this or look what I did here. cause I find it awkward to talk about myself. so I come on podcasts and I do these things and you know, hope people see it and you know, then want to learn more and have a conversation with me. But.

You know, it's hands down the part of my business that gives me the most anxiety. You know, I know that I can serve the clients that I have extremely well. I know I can help them accomplish their goals and do all of the work at an extremely high level. I don't always know where my next client is going to come from. And, you know, that hasn't bit me in the ass yet, but, you know, that's just the reality that I face every day.

15:13 · – Why most guests won't say what Jeff just said (and why it matters)

Jordan:15:13
You have a lot of courage and I really want to acknowledge that within you for saying that in the podcast. I've asked obviously everyone that question, but obviously, but and they say like 10 % of what you just said, but how you articulated yourself right now is how they feel. But they just didn't have the courage to say it. And I just, again, want to acknowledge that within you. Thank you for saying that. No, no, seriously. Like because you

Jeff Lerner:15:37
Thank you.

Jordan:15:41
Yeah, I'm going to sound like I'm from the streets, but you're a real ass mofo for saying I don't know how else to frame it. But like just damn just thank you for saying that.

Jeff Lerner:15:45
You

Jeff Lerner:15:50
Look, you know, I'm, you know, I'm transparent with anyone I talk to. I'm transparent with my clients. I tell them when there are things that are going right, going wrong, when there's, you know, opportunities missed. I'm transparent when I talk to people and I ultimately tell them, hey, I'm not the right fit for you. Maybe I can introduce you to someone who is instead of just taking the business and hopefully trying to figure it out later. You know, because that's That's not how I operate and that's not the lesson I want my kids to learn. That's not, you know, kind of anything that goes along with it. I want to be the best version of myself every single day. And that means the best version of my, of myself for me, for them, for my clients and everyone in between.

Jordan:16:40
No, I love it. On the topic of client acquisition, have you tried anything, whether it's like LinkedIn, cold calling, actively like making time to network? Have you tried anything at all?

16:51 · – The LinkedIn drip campaign he tried, hated, and killed

Jeff Lerner:16:51
Yeah, so I did a little, you know, like LinkedIn drip campaign, you know, thing last year, you know, as a friend had recommended it. You know, I was extremely skeptical going in, but, you know, built the list of founders and all of these things. And to be honest, it performed exactly as I thought it would, which is I had meetings on my calendar and they were either A, ridiculously under qualified of You know, get a lot of like, hey, this is great. I'd love to bring you on. My budget's 500 bucks or a thousand dollars. You know, can you build my go-to-market strategy? You know, or, you know, I would get a lot of, hey, this is great. Like, can you work on equity only? And, you know, while I appreciate the sentiment of that, when I'm not the ultimate decision maker, I am certainly not going to, you know, operate on equity only because it means I am, you know, all the control is lost. or, you know, what was the most common was I'd get on the call and immediately someone would just be pitching me their services and telling me how what they do is better than my LinkedIn outreach. And they're going to fill my calendar with qualified leads. and, so I stopped, right? Like, because it just, it was not remotely delivering an ROI or even the experience I wanted. Like I would. see a call added to my calendar and like get that cringy feeling of like, here we go again. And I just didn't want that.

18:27 · – The wildest thing that happened during cold outreach (people pitching him back)

Jordan:18:27
Damn, the third one you brought up is just jaw dropping. You're doing outreach to these businesses or these individuals and they book a call with you just so they can fix their services. That is so wild. That's insane.

Jeff Lerner:18:38
Yeah.

Jeff Lerner:18:42
Yeah. Cause, cause they would, you know, like, you know, my, the, the, you know, the tool I would have and, the way I pulled, you know, name, you know, it was based on like criteria. And so they were, you know, their title was a founder and CEO or whatever it was. And, know, organizations been around for however long and then they'd be like, Oh yeah, no, no, I'm the founder of lead outreach, you know, company. And like, we can actually get you more leads. And I'm like, Oh, I should have put like some sort of, you know, disqualifier in there for anybody who has like lead outreach in their profile, but So it was just it was far more effort and expense than than value And so I ended that quickly and have no desire to do that again

19:26 · – The free brand assessment on his website and why he built it

Jordan:19:26
For sure. No, I definitely don't blame you, my friend. In regards to your website and the strategy you have from that perspective, love what you're doing. We actually utilize very, very similar approaches internally and behalf of clients. I'm going to say it and then you can obviously expand on it. But basically if you hit Jeff's website, he offers a free personalized audit report on your website.

This does so many, so many things for his organization. One is it builds law of reciprocity, right? You're giving away something for free that's actually valuable. Number two, you're showcasing your expertise without charging any money. I think it's fantastic. Again, we do something similar, but I'll pass the mic to you. Why are you doing that? What's the philosophy behind all that and type of results that you've seen?

20:17 · – Why websites are still just brochures and how to fix yours

Jeff Lerner:20:17
Yeah, you know, it's, you know, I think the mentality has always been, and this is not a knock on the face. It's always been it's, but websites were brochures. You know, you land on the website and it's trying to tell you all the different things that this company can do in hopes that you see something that sparks your interest, that gets you to a point where you're like, okay, I get it. They can do what I'm looking for.

And now my next step is to book a call or fill out a lead form. And so it's a very, you know, one-sided one-way street, you know, type of operation, right? It's I'm putting this out the same brochure out to everyone and hopefully the right people take the action I want them to take and reach out. And so the user really doesn't get value. And I look at it from a different angle, which is if someone's going to come to my website.

I want them to get value, not just in the value of seeing my pricing, for example, right? Like, because you don't want people reach out and they're just, you wait, this guy's expensive. Well, yeah, I have a track record that allows me to be priced the way I am, but I'm upfront about that. So like, I'm not hiding it. I'm giving you that value upfront of knowing what I charge. And so as I thought about adding more value to users who came to the site, I thought, you know what, maybe I can build a tool that can take a bunch of information and inputs from a potential, not even just necessarily a potential client, but from a company and give them the type of thinking that I would deliver to them as well, but in a much lighter version. And so the brand assessment that I built does an analysis of the brand. asks a bunch of questions. you know, as it relates to, you know, how they go to market, what their challenges are. And it gives a really detailed both SWOT analysis and a brand assessment to say, here are some of the gaps that are in existence with your current brand and your current strategy. Now, once someone has that, they can take that in-house, they can bring it to someone else and say, hey, look, based on Jeff's assessment, this is what

22:44 · – How the free assessment turns into paying clients

Jeff Lerner:22:44
some of those gaps are. Okay, if you're gonna take it in-house or bring it to someone else to operate off that, at least I hope I helped, right? Like hopefully I added value. Or in a lot of cases, they reach out to me and say, hey, this was really detailed. There's a lot of stuff here. Like, where do I start and how can you help? And that's kind of the goal for me. So it's both, and again, me being transparent to give value to them. but also to be a lead magnet for me.

23:15 · – Why he puts his pricing on his website (and why you should too)

Jordan:23:15
I love how you get pricing upfront, because I honestly do the exact same thing on my website. You hit my website, there's literally a pricing navigation bar. You hit it, that's on pricing. Not hiding anything about that. I also love the fact that you are providing value upfront. So essentially, our USP, to be candid with you, we run AI-powered email and LinkedIn. Two things that separate us.

One is hyper personalization using enrichment layers and enrichment tools. The second one is opposed to asking for 15 minutes of your time. I'm giving you something of value that's specific to your company. And of course, like you already said it, but it's working. The one thing that I would love for you to kind of play with mentally is we started with the audit some odd, some odd time ago.

And someone broke it down to me like this. They said, when you think of an audit, Jordan, what do you think of? And the first thing I thought of was the fucking IRS auditing my shit, man. I was like, get the IRS out of here. And he's like, okay, if you feel that way, other people may not want an audit. So how can we wrap the audit in a different word that they would want? And I thought, okay, let me think about that. And then I'm not gonna pretend I'm fucking a genius.

But Alex Hermosy has this thing called a scaling roadmap. And I was like, dude, we can call it a roadmap, but it's the same fucking shit that's in the audit, but it's just wrapped in a blanket called the roadmap. like that, dude, that once a week right there has increased like positive reply rates, booking rates, all that fun stuff. So take that and run with it. Don't change.

25:01 · – Why calling it an "audit" is killing your conversion rate

Jeff Lerner:25:01
I may, you know, I've, I've, I've used, you know, in a lot of the outreach that I do and places that post, do more often than not refer to it as an assessment versus an audit. but you're right. The negative connotation that comes with it. But again, we talk as marketers, like, you know, I tell my clients, like, we got to AB test everything. Well, this is a perfect AB test right here is, know, instead of a brand audit or a brand assessment, it's a brand roadmap.

Jordan:25:12
Okay. Right.

Jordan:25:22
And they're like, fuck, same.

Jeff Lerner:25:31
Great, let's test that out, see if that changes anything.

Jordan:25:35
For sure, for sure. Awesome. So happy I added that. Where did you learn to put, like, where did you learn to give pricing upfront? So I am late 20s, early 20s, I got into sales. Grant Cardone was my first mentor, watched him religiously, and he always said, get price upfront, bro. Don't waste people's time. Time is valuable. Give price upfront. That's essentially where I learned. But where I guess, what did you learn? Similar?

26:03 · – Where he learned to show pricing upfront and why it saved him wasted calls

Jeff Lerner:26:03
Yeah, I mean, I think it's that same mentality. And I think it really, it really came to me when I was having all of these calls with founders, you know, even the founders who had good products, good ideas, who like, really did, you know, understand their business and was excited about it. And like, you know, those were meaningful conversations only to get to that point where, you know, I was then like, look, here's what I charge. And, you know, you kind of. like the silence is deafening at that point where they're like, oh man, like that's not even close to being in the realm of what we can, you know. And so I was like, well, how do I, how do I overcome that? And I was like, well, first choice, you know, my first option is like, can start off every call with that, which seems kind of, I don't know. I just felt uncomfortable with that. I felt like it was just a, before we dive deeper into learning about your business, Let me tell you how expensive I am because I'm really good. Um, and so I was like, that, approach isn't going to work. So then it came to, well, what if I'm just more transparent about my pricing now? Like, you know, it's not fixed pricing where it's, know, you can go and click and buy my time on, on, you know, my website. There are ranges, uh, because every, you know, engagement is different.

Um, but it's there to give, you know, someone a little, just a little bit of directionality on what it is that they're getting and what that cost might look like to then also with the experience that I have and the ability to say that I've helped startups raise $425 million. I've been a part of four exits at two and a half billion. Like now you can see, okay, well, this guy charges a good amount, but look at the results he's had, so maybe the value is in fact there and this is worth the conversation that I want to have. And that was the most awkward thing I just said right there and talking about myself and those accomplishments. I felt weird just saying it, but what the hell? It's Friday.

27:57 · – How he helped startups raise $425M and exit for $2.5 billion

Jordan:28:08
Absolutely, absolutely.

Jordan:28:18
I feel like you have to. I know it might feel weird, maybe the mind's... I'm not saying that you're not proud of yourself, but FOR A-

Jeff Lerner:28:26
It's on my website, right? Like I have it on the website. Like I have, you know, so like I tell it, it's just when I like verbalize it, you know, I don't want to come across as, you know, cocky and look at this guy thinking he's, you know, all that because he's, you know, done these things. But at the same time, you're right. Like I am my own marketing engine, right? Like I don't have a team marketing me. I don't have some, you know, Fancy booth at a conference there are never gonna be a TV commercial or a Super Bowl ad of me So all I can do is tell people in the most humble way possible like yeah, I'm I've got a lot of success under my belt I'm really damn good at what I do and I charge accordingly and and if that insults you or whatever it is, I'm I'm I'm sorry and You know, thank you for your attention

29:24 · – Why you have to say your own accomplishments out loud (even when it feels weird)

Jordan:29:24
sure for sure. I consume a lot of I shouldn't say a lot when I have free time, like net downtime, gym, cooking, laundry, whatever. I listened to Alex, Alex Hermosa. He's a good guy. I listened to some AI gurus out there, Nick, like Sarvo, I think his name is but nonetheless, if you listen to Alex's intro, just his hook, he assumes that someone brand new is listening to his content for the first time. And his hook is extremely specific about personal success. Why? Because it gives the audience like justification as to why I should listen to this mofo when there's probably hundreds, not hundreds of Alex's, but a lot of people on, on, on the internet spitting, spitting, you know, free game. And I

Jeff Lerner:30:13
Yeah.

Jordan:30:20
have learned to do that because he's semi right. Why should they listen to me? If I don't verbally actually say why I'm valuable, they're not going to think I am. And like, think about it. Who, I'm not saying people don't do this, but if they're listening to content, they are, they found anyone linked in, only a sliver are actually going to hit your website and read our accolades. But if we just say it in our hook, or say it on a podcast or maybe, I don't know, put it somewhere in our content. It's like, okay, yeah, that's why I should listen to this guy, because he's done ABC. You know, you've done some fucking shit,

30:57 · – The book he's writing and the question his publisher asked that stumped him

Jeff Lerner:30:57
Yeah, no, it's it's it's a great point. You know, I am so I'm in the process right now of finishing up, you know, a book. It's my second book. The first one was more of a hobby project. This one's a much deeper, you know, thoroughly researched case study book all about, you know, founders and how they go to market and brand strategy and separating their products from their brand and all of this stuff. And As I wrote it and after I, you I wrote it now it's, you know, being edited and, we're, working towards that, that final push. one of the questions that the publisher asked me was like, okay, so why are, why would anyone care what you wrote? Like, why you. And, you know, like what makes you better or different than any other fractional CMO brand person, you know, marketing guru, whatever, you know, And honestly, like I sat there like dumbfounded for a minute and I'm just like, I honestly can't sit here and say that I am so unique that I am different from any and all fractional CMO that has ever walked this planet. Right? Like I could never make such a grandiose bullshit statement. But what I can say is I've got 25 years of experience. I've worked at big companies like Google and AT &T. So I understand that world. I've spent the last 10 years working only with startups and I understand that marketplace. I understand that mentality. I've helped them, like I said, raise this money and exit for billions of dollars. And I think my story, my path is unique, but that doesn't make What I do, you know, again, like there are other fractional CMOs who are great. I've met them. I, you know, partner with them if, or refer them if I'm not the right fit for a client. So it's not that there aren't other qualified exceptional people out there, but I have a story and a background and a, and a set of experiences that nobody else has because that was my path. And that's.

33:24 · – Why your story and path are your real differentiator

Jeff Lerner:33:24
The reason why I'm here and I do what I do is because that's my path and that's what brought me here.

33:32 · – You are the brand: How much your personal story actually matters to clients

Jordan:33:32
Thank you for elaborating my friend. And you said some serious shit right there. When it comes to audiences connecting with businesses, brands, and if we refer for actual CMO or a solo operator, you are the brand. How much do you think? that correlation matters between here's like behind the scenes of who I am, here's my story, my accolades, where I come from, et cetera, and how that resonates with the audience. Like I like his story, he's a real human, genuine person. Even though apples to apples comparison, this company does the exact same thing. I'm going with Jeff because I fucking like him. Like how much do you think that matters?

34:13 · – Why Jeff is brutally honest with every client even when they don't want it

Jeff Lerner:34:13
It's, I think it's important and I think it's important in a lot of different ways. You know, one of the ways that I show up every day for my clients is I am brutally honest. You know, if there is something that I don't think will work or a way that something can be done different or better, I'm going to voice my opinion because I feel like that's why I'm hired. That's the role that you've hired for me, even if it's something outside of the world of marketing. and brand, but there's a discussion about operations or business strategy because I've had the experience that I do. If I see a gap or a place where I can add value, I'm going to speak up and I'm going to poke holes and ask questions of the people in the room. Not because I'm just doing it for fun, but I'm doing it because I think or hope or believe there may be ways to make better decisions, different decisions, improvements, whatever. And there have been founders who have said to me after three month engagement, look, this just isn't gonna work. And I'm like, okay, tell me why. And in a lot of cases, the answer is we're just trying to figure out so many things and you're asking questions, poking holes in things. like, honestly, we just don't. want that right now. We need someone to stay in their lane, focus on building a marketing organization, and that's what we're ultimately looking for. don't want, you know, we don't want anybody, you know, pushing back against the engineering team, against, you know, the finance team or sales team or whatever it is. And okay, like if that's your approach, if that's if that's how you want to operate, like I have no problem with that.

I'm happy to say thank you for the opportunity and move on. But that's an important caveat, right? That's my personality is I don't ever want to sit on the sideline and not speak up. And I'll tell you the reason why, true to my core of why I believe that. Even if they're paying me $10,000 a month to focus on the brand, the marketing and all of those things.

36:36 · – Why he speaks up beyond marketing even when he's not asked to

Jeff Lerner:36:36
Ultimately, they are giving me a percentage of their budget of the money they have available because they expect and what their company to grow and to thrive and be more successful. And so even though the money they're giving me is for their marketing side of the business, their brand side of the business, I would feel guilty if I sat in a room and heard things or didn't ask questions. that also would impact the success of the business. So even though it doesn't fall under the purview of my $10,000 investment, it still falls under the fact that you're investing in me to help the organization as a whole. And so that's how I articulate that to clients. And there are some that... appreciate the hell out of that and I'm in every room and every decision because that's how I can add more value. And then like I said, there are some that just that's not how they operate. They want people to stay siloed and focus on the things they're focused on because they don't want the pushback. They don't want to have that part of their culture. And that's, in my opinion, that's not the right way, but it's their way.

37:54 · – What a real CMO does vs. what people think a fractional CMO does

Jordan:37:54
Completely agree. You are a CMO. Forget the word fractional. You're a CMO. Think about what a CMO does. They sit on the board. They're in team meetings. They're a freaking executive within their organization. Like they're gonna poke holes in your shit like how any other CMO would. So to the people, to the businesses out there hiring you or any other fractional CMO, and they do not want them poking holes in their business, shouldn't hire a fucking fractional CMO.

Jeff Lerner:37:59
Right.

38:21 · – The client who called it quits because Jeff asked too many questions

Jeff Lerner:38:21
And that's exactly, you know, anytime, and this is a very common thing, I actually just posted about it on LinkedIn a bit ago, is a client called me, this was last year, but they called me up and they're like, hey, Jeff, we're going in a different direction and you know, whatever it is, okay, tell me more. And their response was like, well, you know, we had been talking about the business was struggling and we needed to, you know, execute comp up with, you know, things faster and.

There was a lot of conversations that I was having with them, but they were also having a lot of other conversations that I was not privy to. And so they came to me, hey, we're going to go in a different direction because we need X, Y, and Z. And I'm like, well, why didn't you ever talk about that? Why is this the first I'm hearing of it? Because we could have gotten in front of it. And the guy started the response was, well, when we hired an agency, we were expecting, and I was like, whoa, I'm not an agency. And he was like, OK, sorry. He was like, but you're a contractor.

And I'm like, herein lies the problem is like, you'd thought like, I'm just a contractor, right? Like I'm because I'm not full time, therefore I am less valuable. And that's sometimes what happens with the word fractional people means well, fraction of time, fraction of cost, fraction of value. And that's not true because yes, it's less time and less cost because your organization probably doesn't need or can't support that level of cost at that time, but you hopefully and should be extracting maximum value instead of fractional value. And so you're dead on like hiring a fractional CMO still means you have a CMO strategy, part of the business operations, part of what is going to get you from point A to point B, not your. the fraction of the business you can focus on is only this.

40:21 · – Why "fractional" gets misread as fraction of value (and how to reframe it)

Jordan:40:21
You shed a lot of light on how maybe some parts of the world view fractional CMOs. To be honest with you, I never thought about it that way, but it does admit other people think about it and you clearly have a firsthand example. I just hear the word CMO and it's like, great, they fucking know what they're doing. Or fractional COO, mean, you don't just. wake up one day and like, okay, will not wake up one day. You can't just spawn into that. You have to have 25 years of experience working for some major, major companies. And then you could have the confidence to step out into the marketplace and become a CMO or COO, whatever the case is.

Jeff Lerner:41:02
Yeah, I mean, I know exactly who I am, what I do, what I'm good at, the value I bring to an organization, the role I play when I'm there, and why that translates into what my business looks like, how many clients I take on at a time, and what I charge for. And I'm going to stay true to that, and I'm not going to mold that based on a definition that others want to put on what Fractional is or isn't or you know what outsourced beans versus doesn't mean that's that's a their problem, right? I know who I am and what I do

41:41 · – Goals for the next 12–18 months: pipeline, AI, and more time with family

Jordan:41:41
I love it, Jeff. I really do wish we had more time. You were one of my favorite guests and I said that on air. Moving into future pacing here. Talk about some goals. What's the number one thing you're looking forward to the next 24, 18 months, 24, months, in the next 12 to 18 months?

Jeff Lerner:42:01
I mean, it's the same things, right? Like I want to continue to learn and grow. part of that is spending more time in AI and learning different ways I can leverage it for me as well as for my clients and adding value on that front. Having a pipeline would be great. So I could maybe sleep a little bit better at night. But at the same time, like I'm fortunate in that because of the business that I've built, like I You know, I don't have guilt when I, you know, take time off to spend with my kids and take them to baseball practice and, you know, travel the world and other things that we want to do because that is ultimately, you know, how I will get judged in my life. It is the role and the impact that I've had on them. And I volunteer a ton, both like at the local school, I volunteer in a local youth organization. I volunteer in a dog shelter. So like, I want to give my time in places that are going to have a positive impact. Of course, I wish I could get paid for all those volunteer things that I love to do, but I want to just continue to do that and have the fulfillment that I get from working with great people who not only I can help them, but they also help me kind of learn and grow and just be a better overall human.

43:27 · – Why he volunteers at schools, youth organisations, and a dog shelter

Jordan:43:27
You're just a wholesome guy, aren't you?

Jeff Lerner:43:29
I try to be. I try to be. Some days better than others, but I try to be.

Jordan:43:34
For sure. then side note, I played baseball for very long time, my favorite sport. So shout out to your kids. That's awesome. What is the single best piece of advice you've ever received?

Jeff Lerner:43:41
Yep.

43:48 · – The single best piece of advice he's ever received: do what you say you'll do

Jeff Lerner:43:48
I had a boss, I don't know, maybe 10 years ago, his name is Bob, and he used to have a saying, which is, what you say you're gonna do. You say you're gonna deliver something on time, at such and such a date, do it. Now, obviously, things come up, but you can go in and say, in advance, right? Like, hey, I know I said I'd get that to you on Friday, like I'm actually a little behind, can I get it to you Monday?

But all the things, right? Like when you commit to something, follow that up. Do what you say you're going to commit to. Because the worst thing is to commit to something, give someone else the calm of, okay, we're in a good shape because Jeff committed to X, Y, and Z. And then if you don't follow through, not only does that impact yourself, but it impacts them as well. And so I... believe deeply in that. when I tell clients, when I tell friends, when I tell, you know, when I commit to something and give my word that I'm going to show up, do this, you know, deliver X, it is because I have strategically and intentionally decided I'm going to commit to that and put my name on

45:08 · – Why broken commitments destroy reputations and kill businesses

Jordan:45:08
That's great advice. A lot of people somehow fucked that up.

Jeff Lerner:45:12
All the time. All the time. mean, just even this week I had an email from someone who's like, hey, I'm gonna get this to you end of day. No problem. End of day comes nothing. The next day I reach out, no response. A day and a half later, hey, I'm working on it. Okay, well, should have been working on it today. And it's just, so I've committed to someone else that, this thing is gonna be done over here. You should have it by Wednesday and then, Come Wednesday, I'm like, I don't know where it is. Like, that's the kind of thing that kills a reputation and kills, you know, the ability to actually build a meaningful organization.

Jordan:45:52
I was talking to somebody else and they're a brand strategist and they said replace the word brand with reputation. That's what branding is. And right there, you fucking nailed it. If you destroy your reputation, your brand, your business brand is gone in the garbage. I love that.

46:09 · – Why every buying decision is emotional the toilet paper brand story

Jeff Lerner:46:09
Yeah, it's the reason why people make subconscious decisions all the time when it comes to their purchasing and other things. And it's all emotional based, you know, and it's, and the only way you, your emotions are either going, there's kind of three emotions you're gonna have. You're either gonna be, you know, like a deep attraction connection, positive. You're gonna be completely negative of like, I will never buy that product brand, whatever.

Jordan:46:20
I just thought...

Jeff Lerner:46:38
Or like you're indifferent, neutral for things that don't matter. Right? It's the same reason why when you ask, and I saw a survey about this years ago, when they asked kids or they asked, you know, early 20 year olds, what brand of toilet paper do you buy? And they would tell the answer and the follow, well, why do you buy that brand? And the answer was always, well, that's just what we always used to buy when I was a kid. That's what was in my house. And it's like those kinds of things. It's a subconscious. Well, if this was good enough for my parents, And for us as a family, then it's probably good enough for my family. Right? And those are the kind of things that like subconsciously you don't intentionally think about. You don't walk into the store being like, what toilet paper did my parents buy when I was a kid? But you see it and you're like, oh, that's familiar. I know that brand. There's some comfort there. That's what I'm going to buy as well.

Jordan:47:31
Jeff, I fucking love it. I legit wish we had more time, my friend.

Jeff Lerner:47:37
I mean, who doesn't want to end a podcast with a conversation about toilet paper?

Jordan:47:41
No, no, no, no. The reason why I get so fucking excited is because the brand strategists that changed the word brand to reputation, I was articulating to them that humans, most humans make decisions based off of fucking emotion. And you definitely expanded on it and gave a prime example with TP. And it's just like, that's why I was getting excited. But like, I fucking love it, Jeff. If they wanted to explore your work further.

Jeff Lerner:47:56
Yeah.

Jeff Lerner:48:05
100%. All emotions.

48:11 · – Where to find Jeff Lerner

Jordan:48:11
at no time.

Jeff Lerner:48:12
They can visit my website at missnomar.co or obviously on LinkedIn. I'm there, I'm visible, I'm posting content frequently. So feel free to reach out.

Jordan:48:29
Perfect. Audience, thanks for so much for tuning in. Jeff, we'll talk to you soon.

Jeff Lerner:48:33
Sounds good, thanks so much.


Questions This Episode Answers

What does a fractional CMO actually do for a startup?
According to Jeff, a fractional CMO listens first and builds a strategy from what the founder and leadership team actually say, rather than arriving with a fixed playbook. The role covers positioning, go-to-market messaging, and bringing cohesion across teams so everyone tells the same story to the market. He also argues the role includes speaking up about operations or business strategy whenever there is a gap, not just staying inside a marketing brief.
Why do so many founders need to change their product before it goes to market?
Jeff says founders tend to think in feature sets, describing what the product can do rather than why someone would buy it. When he asks why questions repeatedly, founders often have an epiphany that the product solves a slightly different problem than the one their target audience actually has. He estimates this leads to some kind of product adjustment about 70% of the time.
How does a free brand assessment work as a lead generation tool?
Jeff built an AI-assisted tool on his website that takes inputs about a company's go-to-market approach and challenges, then produces a detailed SWOT analysis and a list of brand gaps. Visitors can take that report anywhere they like. In many cases they come back to him and ask how to address what it found, which opens a client conversation without a cold pitch.
Does LinkedIn outreach work for fractional CMOs?
Jeff tried a LinkedIn drip campaign and found it produced three types of calls: prospects far outside his budget, founders asking for equity-only arrangements, and founders who booked the call specifically to pitch him their own lead generation services. He ended the campaign and says he has no plans to repeat it.
Why does Jeff publish his pricing on his website?
He found that productive discovery calls would end awkwardly once price came up, leaving both sides having invested time in a conversation that was never going to go anywhere. Putting pricing ranges on the site lets a visitor weigh the cost against his track record before ever reaching out, which means the calls that do happen are with people who have already decided the conversation is worth having.

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