#457 Why Founder-Led Growth Isn’t Optional: Jess Schultz on Early-Stage GTM, Metrics, and Startup Scaling

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Mehmet: Hello and welcome back. New episode of the CTO Show with Mead today. I'm real pleased joining me, Jess. Schultz. Jess, thank you very much for being here with me today. The way I love to do it, as I was telling you before we start the recording, I keep it to my guests to introduce themselves [00:01:00] and I have a theory behind it.

Mehmet: Just I give the teaser for the audience. We're gonna talk about like really important stuff today, all about, you know, go to market, founder led growth, and you know, little bit kinda touch about entrepreneurship and, and maybe. You know, investments and all this, uh, these topics. So without further ado, I'll pass it to you, Jess, and tell us a little more about yourself.

Jess: Sure, thanks for having me. Um, I am based in Miami, Florida and I am a fractional CRO slash cmo, so Chief Revenue Officer slash Chief Marketing Officer for B2B startups. Um, I've been doing this for about three years now. Um, and before that I was, uh, in capital markets SaaS sales, and then I was actually a venture investor.

Mehmet: Great. And, uh, thank you for being here with me today. Just, just, you know, I like always to understand a bit, you know, the reason why you choose this path, uh, when it comes to, you know, assisting, um, [00:02:00] startups and founders. Uh. Mainly in something, which is really tough. Uh, it has been always been tough. Mm-hmm.

Mehmet: I did it for, for quite some time also as well, but it's getting like more tough. So why did you choose, you know, the path of becoming a fractional, uh, C-R-O-C-M-O? 

Jess: Yeah. Um, I, I think probably like most of us, it's a culmination of professional experiences, but I would say, um, my, my most recent role prior to going out on my own was working at a venture capital fund.

Jess: Um, and I was working with a lot of our founders in our portfolio that were C in series A, and I was recognizing how many of them were struggling with different go-to-market aspects. And I felt uniquely positioned to help them because I had worked at really large public companies and seen, you know, what I would consider like best in class sales and marketing.

Jess: But I also understood what investors were [00:03:00] demanding of them, and I also understood what it was like to work at a small. Company with limited resources and limited capacity. And so I think just like the empathy and the understanding that I bring, having had all of those experiences, um, and being able to make recommendations and give advice, um, to them that's, that meets them where they are, that's like still high impact, but is also attainable, affordable within their reach.

Jess: Um, and I just found myself really gravitating toward that. I really loved it. As an investor, you are intentionally not Uber, Uber involved, especially a, a minority investor, like a venture investor, right? Um, and I really enjoy getting in the mud and in the weeds with them. And so I thought, you know what, um, the way for me to embed myself more in these organizations and make a bigger impact is to, to do what I'm doing now.

Jess: Um. So, yeah, that's [00:04:00] how it ended up. 

Mehmet: Great. Yeah. So I gotta go, come back at some stage to the investment part, but for now, I know that you specialize Jess in mainly founder led growth. Mm-hmm. And I have a theory myself. I'm not sure you're gonna share the same, uh, thoughts about it or not. Uh, I'm seeing like more and more people.

Mehmet: Having success when, when the founders themselves go out and put themselves. But it, it's, it's, it's kind, it's not like a new completely, but it also breaks a little bit, you know, the traditional, you know, uh, concepts that people, they had about, you know, how to start a sales organization within a startup.

Mehmet: So from your experience, like what have you seen, you know, like majority of the time, the, I would say. Mistakes. You know, the founders make, you know, when they try maybe to, to do that by themselves. Uh, or maybe they, they choose [00:05:00] different path and then they come back to this. So what leads, you know, for a startup and of course the, the founding team to go and follow the founder led sales?

Jess: Well, I personally believe every company should start that way, and there's a, a few reasons why. Um, one. No, usually no one has the depth of knowledge about the industry or the target customer that the founder does, or founders, whoever those people are. Um. So, and I'm sure you know this 'cause you talked to a lot of founders, but so many founders have created solutions that solve problems they experienced firsthand.

Jess: Um, so it's a lot of times like they were their target customer or they're solving problems in industries that they've lived in and breathed for years. So they just have this depth of knowledge that no sales person they can hire is going to have. [00:06:00] And they have this passion about it, you have to, right?

Jess: Like why else would you take the leap? Like starting a and building a company is not easy, so you have to really, really love it. And I. And you have as the founders, um, the most investment, like time, energy, reputation, money, um, in the outcome. And so for all those reasons, you are the best seller. You are the most knowledgeable, the most hungry, the most passionate.

Jess: Um, and you are also the person that is, especially if you're founder, CEO. In charge of the engineering team. So I really think it's so important for founders to be front lines, having those con first sales conversations and getting that feedback and being that feedback loop to engineering for the product roadmap.

Jess: Um, I don't think anyone else can do that job, but the founder at the very early stage. But then there is a point that that becomes. Like untenable. We can't have the founder being [00:07:00] the sole producer forever. So I personally counsel people to be founder led sales until you get to at least early signs of product market fit, which is different for every company, but for most of the companies I work with that are B2B SaaS selling into like mid-market or enterprise, that's generally speaking around 10 to 12 customers around, you know, a million a RR.

Jess: Um, is generally when it's like, okay, we we're seeing early signs of product market fit. We have a handful of really happy customers. Um, now we can try to professionalize this and bring on a salesperson, but I think if you try to, and I've seen people do it, I'm sure you have too. If you try to bring on a salesperson earlier than that or a sales leader, it typically doesn't work out right 

Mehmet: now.

Mehmet: Uh, from what you have noticed, Jess, like, what do you think? You know, some, [00:08:00] because usually when I talk to founders, majority of them, they come from non-sales background, right? So they are like probably techie people. And one, I'll give you an example and maybe you, we can discuss this. So, because they, they are so excited about the product, right?

Mehmet: So. Uh, do you see like sometime they think that they are doing the right things when they, it comes to selling. Um, so maybe they are like, uh, putting a lot of bets, uh, on some of the customer that they think they're gonna definitely like get this revenue from them while they are not, of course following what usually.

Mehmet: Probably someone who would have an experience in, in selling, especially like enterprise and, uh, you know, B2B SaaS and other solutions would, would like really qualify this and, you know, understand like what are the sales cycles for these customers. So have you seen like these also kind of challenges with the [00:09:00] founders you work with and you know, how they can, if I want, and this is the question I want to reach, like how they can educate themselves, uh, beforehand, you know.

Mehmet: Putting themself in front of, of, you know, the customer so they prepare also themselves and they don't feel disappointments, you know, in the future. 

Jess: Yeah, yeah. Um, you're absolutely right. I still think even a founder with no sales training is usually not that bad of salesperson in my experience. Like, because it's almost like, because they're not a salesperson, they're more convincing, meaning.

Jess: They're not coming in with a sales title where the, where the person on the receiving end, the prospect is like, oh, this person's just trying to sell me something. They come in with this like passion and love for what they're doing. And even if that doesn't translate into a perfect sales process, it's still convincing and people still are interested.

Jess: So even the worst founder sales person, I think is usually not that bad. Um, [00:10:00] but to your point, a lot of them do come from technical backgrounds and they don't have what we would consider like classical, classically trained sales and marketing, um, skills. And so the. To your point, the best, like when you can find a founder that really wants to learn, which I think they have to really want to learn, and then you can provide them with resources.

Jess: Maybe somebody like me, like a fractional, uh, go to market executive or maybe like a, a go to market coach. Like there's obviously a ton of executive coaches out there now too, so you could find someone with a sales background that can at least just give you like some basic fundamental knowledge of best practices of.

Jess: You know how to run a discovery call. To your point, like how does enterprise sales work, like what are the different stages that you should be preemptively expecting to go through, like procurement and things like that? Um, so if you can find someone, a coach or an advisor to kind of help show you the ropes, like then you are gonna be [00:11:00] infinitely better off.

Jess: Um, so yeah, I would counsel people to, to hire someone as a go-to-market advisor, executive or, um, and or like seek out knowledge. There is a lot of great free knowledge out there. Like I run a newsletter, um, every week where I share free tips and tricks in education. Um, there's several other people in, in my or in our industry that do the same.

Jess: Like there's several other thought leaders that produce content just towards tailored towards founder-led sales. So I would say seek those resources out. Yeah, 

Mehmet: right. Mentioning content. Jess, and uh, you know, this is something I started to notice recently, especially, uh, everyone is talking about, you know, the nimble startups who would be operating in minimum resources.

Mehmet: And we are seeing like more this, I would call it a school where founders themselves, they go work on the content also as well. Yeah. So they start to offer, you know, [00:12:00] the kind of thought leadership on. Like different platforms, of course. Link it, link it in because it's like more for B2B people. Um, is this something you.

Mehmet: Like first, like your point of view on that and do you think like, this is the way moving forward, like instead, because people usually start our founders, like if we ask them, I don't know, maybe 5, 6, 7 years ago, you know, they have this playbook of going running ads, you know, running some, uh, focus groups and things like this.

Mehmet: But it seems like the game completely changed today and we are trying, we, we started to see this. From founder led perspective also that they have to put themselves out in front mm-hmm. Of the customers and talk about, you know, and what they are doing, what they are building and build this empathy. So what you can share on, on that with a Jess?

Jess: Yeah. Yeah. Um, I'm a hundred percent a fan of that and I recommend all of my clients do it. Um. Uh, there's a [00:13:00] few reasons why. If it helps convince people, um, one, there's statistics that show that when a marketing or, um, when a content message comes from a person, like from a human being versus a brand account, it has over 500% more engagement.

Jess: So, like we as individuals have. Much more reach than an, than a company account ever will. Um, and I'm sure you can figure out why, right? At the end of the day, we all are people who buy from people. And so the more we can get to know and, um, learn about a person, which a lot of you you can do through thought leadership as you're really let letting people in and letting them get to know you, letting them get to know how you think, um, the more you're going to attract them to you.

Jess: The other reason is your brand doesn't have, if you're a startup, a lot of recognition yet, right? You're not Salesforce, you're not AWS, nobody knows who your startup [00:14:00] X is. Um, but presumably, you, the founder, have a brand already. Like before you even started this company, um, you, you know, I don't know. Were an early engineer at Google.

Jess: You were. Whatever, the founding engineer at a company that exited, like you have a brand, you have a story. And so that's the brand that you need to leverage at the beginning before people really know who your company is. Um, and then the last thing there is just, um, the first thing you need to do as a founder, right, is build an, build an audience like.

Jess: Uh, and ideally of your target customers. Um, and the way that you attract them to you is through sharing helpful, thoughtful insights about whatever your. Your industry or your niche is, um, the founders that I've seen do that really well where they just build like this community or this audience of their prospective customers.

Jess: 'cause as I'm sure you know, a lot of times when you're starting out, [00:15:00] your product might not even really be like an MVP. It might still be an idea held together by duct tape. So you don't have much to sell yet and you certainly don't have something to sell at scale. So if you can start building that audience while you build.

Jess: Your MVP or your product that's like ready for market. Um, then when you have your product ready, you've presumably already just. All you've done is give value to this audience for X number of months. Um, and so now you've earned the right to ask for something back and so you can promote your product, um, or whatever it is, and you're gonna have a lot easier time in my experience converting tho that audience into paying customers.

Jess: 'cause there's already trust and familiarity. You're not just coming out of the gate. Um. At that point with, with no audience, with no feedback, and it's a really quick way to get marketing and sales and product feedback. Honestly, it's like the fastest and [00:16:00] cheapest way to have that feedback loop. 

Mehmet: Yeah. Uh, what surprises me sometimes, Jess, is uh, what we are describing is kind of, if you go like any book that talks about, you know, startups and operations, mainly sales and marketing, so.

Mehmet: The, you know, he, one of my favorite, Steve Blank, right? He always talks about going out of the building, talking to, to customers, trying to get the feedback. But I still see sometimes for some reason, I, I'm trying to still find out why I can relate it psychologically, you know, to some aspects of, you know, maybe the excitements, maybe sometimes, you know, like, uh, um.

Mehmet: I would not call it ego, but I would call it, yeah. Like I, I know what I'm building and I should like, just put it this way. Yeah. And then I would, I would position it now, uh, this is where I think, you know, it's very important to listen to, to the customers build, you know, this momentum with them and then take it forward later on now.

Mehmet: Uh, you, [00:17:00] you mentioned about the different stages, so of course there is the first stage where still, as you said, maybe they have the duct tape and trying to to sell the idea at the beginning, and then they will have an MVP, maybe early signups now at some stage and. I don't know if it's fair to say like the $1 million a RR let's say is the fair number to say like, okay, now we need to do the transition to the next phase of our GTM.

Mehmet: So how do you find, how do you define this? Just like, is it based on the revenue? Is it a mix of revenue plus maybe, which exact like vertical they are targeting? How, how do you define, you know, what should be the next phase of scaling the business? 

Jess: Yeah. Um, there's no perfect answer to your question, but I can tell you like some signs that I look for, right?

Jess: Me and I say there's no perfect answer because every business is so different as, as I'm sure you know. But again, in general, you need to have a [00:18:00] handful. So again, that's, I mean, at least five, but I would think maybe 10 is, is a better number. And I'm just picking an arbitrary number. But the point is like a handful of customers that are not just.

Jess: Your best friends that you used to work with. And so they took a bet on you, but people that actually brought, bought your product either through like you going cold outbound to them or you getting referred into them, but like a handful of customers that, that, again, were not your best friends or, uh, existing re like deep existing relationships.

Jess: 'cause that's evidence that people are. People that don't, that aren't your best friend, are willing to pay you money for what you've built and like, that's a good first sign. The other sign I would say is like that. There's at least some observable trends within that. That little customer base that you've built, right?

Jess: If every single one of them looks and feels different than the other, that's also not product [00:19:00] fit. That product market fit. So I would say like you wanna see like, okay, in general I am, you know, I've now closed roughly 10 customers. They're all, you know, 80% of them are in healthcare, 20% of them in financial services, meaning a hundred percent of them are in highly regulated markets.

Jess: They're all about the same size. They all bought from me for roughly the same reasons. Like they're, they were resonating with the same value props, and they're happy, they're loving the product and they're super fans of what I've built. That to me is like, okay, now we have something to work with. Like we know that.

Jess: This is roughly what our target customer looks like. This is roughly why they're buying, and we can go out and try to find more people that look and feel like them. Um, but you, until you have that, I don't think you're ready for professional, like professionalizing and scaling anything. You have to get that first cohort, and they have to at [00:20:00] least have some common attributes 

Mehmet: right now.

Mehmet: When do they transfer from, you know, relying. And I know like, it's not only about, uh, fractional CROs, so we are seeing like even fractional, um, CTOs as well. We, we are seeing the fractional momentum picked up a lot. And of course it made a lot of sense. Uh, but when do you advise them to go and have like a sales leader, uh, in the organization?

Jess: Not for a while. Um, I would say like, um, I try to counsel founders, in my opinion, you, you are the reason why we got wherever we are. Right? A million or 2 million a RR like you, you're the reason. Um. So we can't just immediately remove you from the sales process and expect there not to be disruption. So we need to peel you out slowly.

Jess: It's an, it's a slow like step back, right? And so I think of it [00:21:00] working the best when you peel off from the top of the funnel to the bottom. Meaning like maybe the first thing we hire is like an SDR or a marketer, like top of funnel demand, gen support, where the founder's not having to do as much of effort to set new meetings.

Jess: So they're getting some support on that end, but then they're still really the one project managing and closing the deal. And then we try to bring in maybe an account executive. That can project manage most of the deal. Right. Um, but I would still envision the founder being the acting sales leader for that account executive.

Jess: Not, not just bringing in a sales leader, um, because you want the founder still involved in the deal in particular, like later on in like the proposal pricing and close. So maybe then again, we've moved them out of top of funnel demand gen, we've moved them out of like. Qualifying the opportunity and doing a demo, but then we're still bringing the founder in after a demo to help [00:22:00] close the deal.

Jess: And then like the final stage is, okay, now we've got one, two, maybe three account executives consistently, uh, running a process and, and having similar results. Now we're ready for a sales leader to manage them and for the CEO to like. Not, I don't think they should ever be not involved at all, but like maybe they're just getting brought into the biggest and best deals at that point.

Jess: Or when we think a deal is like losing momentum, maybe they come in so they're more like. One of my clients called it Santa Claus. You know, like they're more like, like less frequently showing up and making everybody happy or helping something along, but they're not having to be involved in every deal in the pipeline anymore.

Jess: But like, that's how I think about it, is start at the top and like slowly peel them off, um, little by little. 

Mehmet: Yeah. And um, I like the Santa close, so we use the Santa close all the time. Like even when the [00:23:00] company becomes like, uh. A public company because sometimes, you know, getting, getting the executive sponsorship is very important.

Mehmet: Um, I, I, I've seen it like, uh, also a lot of times it works really because it shows also like kind of, uh, you know, the customer feels they are important. You're important. Yeah, exactly. Now, uh, especially in the first, you know, couple of years, there are a lot of metrics, Jess, that people looks at and. People have different opinions.

Mehmet: So people, some of them, they focus on a RR, they don't look at anything else. So a RR all the way, no one looks at the burn rate, the cac, you know, and all the other things. Some people, they look at profitability. So, and I'm asking you this because you sit also on the other side of the table as an investor.

Mehmet: Mm-hmm. So in your opinion, what really should be the metrics that. Are the number one priorities for founders, especially in, you know, [00:24:00] let's say below the mark of 10 million, uh, revenue? 

Jess: Yeah, I think, um, I mean to your, there's different, to your point, there's different phases, right? So when we're trying to get to product market fit, you're, we're not looking at scalability really, right?

Jess: We're just literally trying to learn from every single customer interaction, customer conversation, and. Get to a point that our product is priced and packaged as such that it's palatable and purchasable. So like there's nothing that I, I think like that beginning part is all about learning and logo acquisition, like finding those early adopters.

Jess: And then once you have a handful again of those early adopters, and now we're trying, starting to say, okay, there's some, you know. There's some signs of product market fit here, then you're moving into like, how can we make this repeatable? Like to me, that's the next focus that you should have is just like, how do we bring some rigor and structure to this so that we're, we [00:25:00] can repeat, we can rinse and repeat over and over and over again.

Jess: And that might not come with, again, perfect metrics, but it's just about finding that repeatability. A lot of times I say like, go to market is a lot like a science experiment, and if we're changing too many variables all the time, we have no way of knowing which variable impacted the outcome. So I would say like that's the second goal.

Jess: And then once you have repeatability and you actually have metric, then you finally have metrics that we can actually look at with some. Um, confidence to like, inform, getting to scalability. And then I think you start really looking at like cac, LTV conversion rates, deal life cycle, like. Um, I tell founders when they're first starting to like, dig into metrics, if you will, like what I counsel them to focus on first, um, from just like, again, sales and marketing is, um, where are my deal?

Jess: How many new [00:26:00] deals am I creating each, you know, week, month, quarter? Um, is that enough? Statistically to hit my goal and there's like math that we can do to back into that, right? If we know that our revenue goal for the year is 2 million and we know that our average contract's 50 K, we can, we can back into like, okay, that means I need to have X number of conversations to get to X number of closed one deals and hit my number.

Jess: So like number one thing I counsel them to start tracking is just like, do we have, are we creating enough top of funnel? To even come close to hitting our numbers, yes or no? Then where is that funnel coming from? Meaning like the source of the deal. Is it coming from marketing? Is it coming from referrals?

Jess: Is it coming from outbound? And does that reflect the effort and investment that we're making in those areas? Meaning if I'm dropping 10, 20 grand a month on marketing. But I'm not getting any leads from marketing. And you do have to give these [00:27:00] things time, like four to six months usually for marketing.

Jess: Then that would be really concerning to me. So I wanna know like, does the source of my current pipeline reflect my current investments in go to market? And then, um, the next thing I would start to look at is like, how am I converting? And it specifically, like at each stage, like how many of my deals are moving from first call to demo, demo to proposal, et cetera.

Jess: Where is it? What we call pipeline leakage? Like where is my pipeline leaking? I. And then can I figure out why is everything falling off at pricing? Okay, why do I have a pricing problem? Do I have a problem with the way I'm presenting the pricing? And that's where we have to get, you know, diagnostic and figure it out.

Jess: But like, figuring out where your funnel is leaking is the next thing I counsel Linda to do. And then finally, like, how long is it taking me to close these deals? Um, and is that getting shorter as I like, that's the goal, right? Um, is to [00:28:00] accelerate. Deal, um, momentum. So I would say like, those are the things I say to start with, and then we can get into again, like more advanced metrics.

Jess: But I'm like that if you don't have that under control, the rest doesn't really matter. Right? 

Mehmet: Like, 

Jess: yeah. Right. 

Mehmet: Um, now the very famous debate, especially when it comes to B2B, SaaS and actually any, any B2B Tech, I would say all of them, they are SaaS, but anyway, um. Outbound, uh, reach, you know, inbound reach marketing.

Mehmet: We don't have resources. We need to do a lot of, I don't know, like, uh. Like cold calling LinkedIn campaigns and it seems like, you know, the space is being disrupted as we speak, Jess. Yeah, especially with the AI and you know, all the, all the things there. Um, I'm hearing different opinions. Some people they say yes till it's working, like business as usual.

Mehmet: Some people, they're saying no, [00:29:00] buyers like kind of, they are different now in their way of how they find solutions, how they want to be reached out. What are you seeing in this space, Jess, and what is your take on, you know, the outreach and all these, uh, you know, other tools that usually we used to use them back in the days and still we use them kind of also.

Jess: Yeah, yeah. Um, I think it's a, it's a yes and like, yes, a lot of the old tactics still work and they need to be modified for the current environment. Um. Like, let's take outbound for example. Like I still run outbound with, for, for my customers, and it does work to a degree. Um, I would say like some things that we've, that I've done with them to like make it more effective, for example, is like, I.

Jess: Email is harder nowadays. I'm sure you know that just because like Google and Yahoo came out, I guess it was about a year ago, and added additional [00:30:00] security protocols and like parameters around what you can and can't do with cold email. And so it's, and, and we're seeing an uptick in like cybersecurity threats and things like that.

Jess: So especially if you're targeting like enterprise level customers, it can be harder to even just get in their inbox, right? Like email deliverability is just harder because of those. Those things. Um, so I've moved a lot of my outbound with customers to LinkedIn because I find that it's more effective because we don't have the email deliverability challenges.

Jess: Again, these are like early stage startups too. Um, I also find that if I have the outbound come from the founders' identity versus a salesperson, it has a higher impact and higher response rate. That's probably obvious. As to, to you as to why. Um, and then, uh, I definitely do not use AI to write my outbound messages.

Jess: I'm, I am. I have strong opinions about that. I just think like an outbound message is already cold. We [00:31:00] don't need to make it colder by not having a human write it. So like personally, I write or cancel my clients to write the messages themselves. Not use AI for that. But you can still automate it at scale as long as you segment your lists and you segment your messages with the list accordingly.

Jess: Meaning if I pull a list of leads that are all hiring for COBOL engineers, and then I write copy about that, right? Like the fact that I observed that they're, they're hiring for a COBOL engineer and I automate that list. It's still scalable. It's still automated, but it's targeted and segmented and thoughtful.

Jess: It's not just spraying and praying every organization that we possibly can. So I think. That's a long-winded way of saying like, yes, outbound can still work, but I think you do have to adapt the way that you're doing it and be a lot more intentional and a lot more thoughtful. And I personally don't love using AI for the reason I just said, uh, at least to write the copy.

Jess: [00:32:00] Um, and. Um, I also counsel my clients though that like outbound is and has always been the lowest quality source of business, right? Like there's tons of statistics that show that like if we get our lead from cold outbound today or 10 years ago, it's not as high quality as if we get a referral or if we get an inbound lead.

Jess: And that's because of trust and timing being so paramount in every sales. Process, right? Like you have to trust the person that you're buying from and you have to get timing right. And so referrals and inbounds generally have trust and timing a lot more strong than outbound does. So it's like we can do outbound, but we also need to be doing other things to get higher quality deals in our pipeline that have a higher propensity to close.

Mehmet: Right. Uh, I'm not fan of outbound, honestly. Uh, of course, other than the sense of, you know, what we call it, uh, nurturing, you know, we, we had like collected some leads [00:33:00] at some stage. You know, we've, we've got them into the database somehow and Okay. I, I'm fine with that, but not as a way to go and just say, hey.

Mehmet: Um, and to your point, like, yeah, the AI made it worth like, Hey, like I've seen you did this at your company. And, you know, majority of the time now, if I was getting like 2% of them e the cold emails I used to receive like something very generic and wrong about me. Now I'm getting that even more worse because, you know, it looks like ai.

Mehmet: Yeah. You know, and I have a very tricky LinkedIn profile, I have to admit that. Uh, so the AI doesn't understand what exactly I do. And it, and the message is very funny because, you know, yeah, uh, uh, I say, Hey, and if you are not the right person to talk to, who would be the right person? And you know, the first thing it'll be, ah, you are the founder.

Mehmet: Anyway, it's like really interesting times for us. Um. Now back to, to, to the marketing part. And [00:34:00] because you are also acting as a fractional CMO Jess, uh, for, for your clients. I'm a fan of marketing by the way. Mm-hmm. Uh, uh, like every company I work with, you know, people, they used to like the salespeople get that tension.

Mehmet: Don't get me wrong, marketing, they do the heavy lifting in my opinion now. Yeah. Um, you mentioned about the use cases and starting, you know, to build these copies, you know, of, of things that really the customer would be looking for. Um. Anything you can give us examples of maybe success stories you work with, maybe some of the startups you helped in building these collaterals, in building, you know, these, uh, um, you know, copies that give generality, that gives also the customer the feeling, oh, these guys, they know what they're talking about.

Mehmet: Like, I should consider at least taking a, a meeting with them. Mm-hmm. And then see how we can move forward. So maybe you can share some insights on this [00:35:00] also as well. 

Jess: Yeah, that all starts really with like effective marketing and sales. All starts with really strong understanding of your ideal customer profile and buyer personas.

Jess: Um, and then really good positioning. So like I always say like those are like the fundamental, you know, compass and map that you need for everything else to be effective. Um, so that's where I start with my customers is okay if you have, if they already have customers, which usually by the time they come to me they do, I'm like, let's analyze your existing customers.

Jess: Let's take a look at like, what are the commonalities amongst these companies. What are the commonalities amongst why they bought from us? Um, and there's some real deep dive exercising that we do to just get like really clear and, um, prescriptive about what those people look like. And I can give you an example that I've given a few times that, uh, people like, it's not just even also like the person and their title, but [00:36:00] like what about that scenario?

Jess: Could we try to recreate? And what I mean is like one of my customers sold to, um, heads of benefits at Enterprise, uh, like employee benefits at enterprise organizations. And we analyzed his, you know, last five or six, uh, buyers, if you will, that were like really champions of getting his product through the door.

Jess: And we noticed not only did they have a head of benefits title, but they all had MBAs. They'd all been in their role three years. Um, and they all also worked at Big Four Consulting before they were in their current role. And we think that mattered because we think the three years mattered because they probably didn't.

Jess: Most people don't come into like Microsoft as the head of benefits and have the political clout to get. A $500,000 or a million dollar purchase done in their first year. Right. You probably have to come in and build those relationships, understand the existing state of affairs, [00:37:00] understand the internal politics, and then you can probably like.

Jess: Push something of that size through. So we think that that three years mattered for that reason. Like their ability to navigate the org and have like the um, the capital that they needed to be a good champion. We think it mattered that they had an MBA because the product my client was selling was just very cerebral.

Jess: Like it was very analytical and we think like maybe those more academic backgrounds could connect with it more. Um, and we think the Big Four consulting mattered because they were used to big change management and project management. And so maybe they were better at organizing the deal internally because they had those skills from Big four.

Jess: So like, that's like the kind of granularity we try to get to. Um, and then I also personally try to interview their customers as well so that I can, I can ask them second layer questions to confirm my hypothesis, um, and, and then bring [00:38:00] all of that together. And then again, that becomes like the compass, the map that then drives effective sales and marketing.

Jess: 'cause then we know exactly who we're going after. We know exactly how to talk to them, and then everything else gets more effective. Then I would say like the other part is just like consistency. Like so many startups with marketing anyway, you can't just market for a day, a week or a month and have results.

Jess: Like it has to be a consistent, methodical. We show up every day. We show up every week, and we do, we do the steps, we do the fundamentals, and after, in my experience, four to six months of being really consistent. With really good compass, you start to see the results and then you have to of course maintain it.

Jess: But I think too often, and I get it, I'm super impatient. Startups get really impatient 'cause they're just thinking I did it, now where are they? And I'm like, no, we have to give it time. Um, and so I think they [00:39:00] quit too early or they change course too frequently and so we don't give it enough time to like really take hold.

Jess: I think that's the other like challenge I see. I. 

Mehmet: Great. Now a question related a little bit to, to. You being an investor also Jess, and I believe you still do kind of angel investment. Now when, when you have, when you have a startup pitch deck in front of you, so do you look at it from your, you know, venture capitals background and you know, the work you you did before?

Mehmet: Or do you look at it as a GTM practitioner and startup advisor in that domain now? Like what, what do you think is like more, I would say, uh. Dominant on when the way you start to analyze their pitch deck, like what really makes you decide like, okay, these guys, they are all say, you know, maybe second beating or, I don't know, maybe a follow up and due diligence 

Jess: and You mean for just as an angel investor now?

Mehmet: Yeah, as an angel investor now. 

Jess: Yeah. Um. [00:40:00] As an angel investor. Now I personally only make investments in companies where I think, and I think this is true of most angels, I think, um, where I think I can personally contribute beyond my capital. 'cause my capital as an angel is not. I am not writing them a million dollar check, right?

Jess: It might be like five, $10,000. Like it's, it's relatively small investment, so it has to be something where I'm like, I think I can help them with my network, with my skillset, with my knowledge. Like sometimes I know the industry they're selling in super well from my prior experience or something, so I have to think I can add more than my cash.

Jess: Personally. Um, and then I personally look for founders where I think that they are displaying, like, that they're very coachable and, um, that they're the right founder. Like there's founder market fit, if you will, like that they're the right founder to drive a solution for this industry or problem. 'cause I don't always think we see that, um, sometimes.

Jess: So I just, if I'm like. [00:41:00] Okay, you're building a legal tech solution, but you're an engineer and you've never worked in law. I'm like, I don't, that doesn't feel right to me. So like that to me is like a no go. Um, uh, and then the last thing I look for is like, can they build an audience and a team? Um, like do I see those natural sales skills because, and marketing skills, I guess because that's so much of what the early company success depends on is like the founder's ability to.

Jess: Not just find clients, but find investors, find teammates, like convince people to sign on to this very tumultuous ride, right? Like, um, and so if I don't see those soft skills, to me, it's not a go. So I would say like those are my first, um, like go no go parameters. And then I might look into like, okay, is there also like a sizable market here?

Jess: And like some of the more. I don't know, [00:42:00] traditional like investment evaluation, but also at an angel stage. It's so early. I know, and I've seen it firsthand that the what you. Buy into could look very different in one to three years, you know, just because, and that's not always a bad thing, it's just like they're gonna get feedback in the market and they're gonna pivot and evolve, or their competitors are gonna evolve or whatever's gonna happen.

Jess: So I think you really just have to, you're, as a million people have said before, you're betting on the jockey, not the horse. So I think it's like. So much more the person than anything as well. Ab. 

Mehmet: Absolutely. And I believe just like your, you know, the, the, the founders you work with, they benefit a lot from your VC experience in a sense.

Mehmet: Like probably when they gonna go and raise maybe for their second round, um, you know, their series A and above, so. Uh, anything usually also, like other than revenue, revenue is, is very important. Mm-hmm. Especially when you are in the, but anything else you [00:43:00] advise founders who, uh, let's say they crossed the right, so, so they, they found the product market fit.

Mehmet: You know, they found a successful formula. They found the right distribution. They found, you know, uh, all, you know, they ticked all the boxes like. Do you help them also in being prepared for the next phase of fundraising as well? I mean, not in a sense of you funding them, but you know, being ready to, to be in front of the, you know, traditional VCs, I would say.

Jess: Oh, totally. Like to your point, I'll talk to them about like, you know, a series A investor's gonna be looking for X, Y, and Z. We don't have Y and Z. Here's what we need to do to get those so that you can go out with much greater like odds of success than you have right now. So like sometimes I'm just educating them on like what the investor's going to expect or what objections to preemptively predict.

Jess: Right? Like. You know, sometimes it's like, look, you're, [00:44:00] um, I don't know, maybe there's co like little things that I just know are red flags for VCs, right? There's co-CEOs, they don't like that. They wanna see one CEO. They don't wanna see two. Like that's gonna be something you should either fix or you, you better have a really good answer as to why.

Jess: You know, they shouldn't be worried about that. Or like, they're not gonna like, um, you know, I'm trying to think if, like, sometimes startups will try to use like a third party capital, uh, introduction person and at Series A that will turn a lot of investors off if you're, they're like, why do you need someone to help you with a series A, like maybe Series B and beyond?

Jess: Sure. But you shouldn't really need like this sophisticated third party at. So there's just like little things that I know from being an investor that I'm like, don't do that because that's gonna turn people off and here's why. Or if you're gonna do that again, be ready to talk about it because that's gonna be a red flag, um, for people.

Jess: And so I think I just try to counsel 'em through [00:45:00] those things in addition to like what to expect or how to be ready. 

Mehmet: Right. I think, you know, the, from my conversation with you, Jess, I think the founders are lucky because, uh, it's not like only you give them hints in the GTM part, but also like being prepared for the next phase of fundraising, which is, in my opinion, very, very.

Mehmet: Important. Uh, although like we still, we still see sometimes with hey, like, okay, why you don't keep it like, as is I, I big believer that if you want really to have impact and, you know, grow the company to where really the founders had their passion and, you know, the, the, the long term goals they wanted to achieve, they need to pass these phases and, you know, hopefully, you know, they, they will reach, you know.

Mehmet: The numbers and uh, uh, goals that they have set up for themselves. Yep. Just like as we are coming close to an end, uh, and this is a maybe kind of traditional question, but you know, what kind of final, you know, I would like to call it sometime, word of wisdom, [00:46:00] final advice you want to share with the audience today, and of course where they can get in touch.

Jess: Yeah. Um, I would say like, things I usually leave founders with are just like, don't like. Don't underestimate how important it is for you to learn the fundamentals of sales and marketing. Um, truly to know them. Because I think too often founders hire, I. Um, you know, like an ad agency or an SEO agency or whatever, and they don't really even understand what good looks like or what questions to ask or if that's even appropriate.

Jess: Um, and so I would just counsel people like, as much as you can, learn the fundamentals, because you're gonna be much better positioned to vet either new hires, freelancers, agencies like you're, you're gonna know the right questions to ask and you're gonna know the right things to look for, to know if it's.

Jess: If it's working or not, like you're gonna be able to, um, to monitor and manage it better. Um, so I just [00:47:00] really try to counsel founders, like educate yourself. Um, I run a weekly newsletter where I give out free tips, tricks, knowledge, um, and again, there's several other people in my space that do this too.

Jess: Some other like investors slash people that I think are good. Uh, for, for folks, our um, April Dunford is amazing position B2B positioning expert. So go buy her books, listen to her podcast. She's phenomenal. Um, Kyle Poya. Foer, I think is how you say his name, but he's a ex OpenView, um, investor and he talks a lot about go to market and product-led growth.

Jess: Um, forum Ventures is another, they put together a ton of, they're like an early stage pre-seed seed investor, but they put out a ton of great free educational content. So just go educate yourself as much as possible. That would be my final advice. Um, and yeah, keeping in touch with me, you can find me on LinkedIn.

Jess: I'm very active there. And then again, I run a newsletter. Um, I can send it to you to put in the show notes. [00:48:00] So would invite you to sign up for that if you'd like. And thank you so much. 

Mehmet: Great. Thank you very much, Jess. And of course, they will find all the links in the show notes. They don't need to look and go and search.

Mehmet: And really, I enjoyed the conversation. Probably, we hope because we share like also the same background. So this makes the life easy for me as a host when asking the questions, uh, and also make the life easier for me when, when you get the answers, uh. This is for the audience. As I told you, you will find the show, no in the show notes, the links for Jess, for her newsletter and her LinkedIn profile, and the website of her company.

Mehmet: Um, uh, also as well, and as I say, always. Thank you very much for, you know, coming and listening to the CTO show with Mead. If it's your first time, thank you for passing by. Give us a thumb up, share it with your friends and colleagues and subscribe and if you are one of the people who keep, keep coming again and again.

Mehmet: Thank you for doing so because of you. We are doing fantastic performance this year. [00:49:00] We are like ranking in the top 200 Apple Podcast chart in multiple countries simultaneously. I never seen this before. And of course, because of you, we were chosen to be one of the top most listened, uh, business podcast here in Dubai.

Mehmet: We are in the top 40. Thank you for also choosing us, and as I say, always stay tuned. We'll be again in a new episode very soon. Thank you. Bye-bye.