Outfoxed Podcast by Hunter.io | Ep 18 Stefano Ferrara “Unifying sales and product led growth”

This is Outfox, the podcast brought to you by Hunter.io, the trusted B2B lead generation platform built for every professional. Get ready for no playbooks, no posturing, and no egos. This is the show for the builders and not the theorists. Let's get into it. >> Hey everybody, welcome to Outf Fox. Excited to be here and uh super excited to introduce you to Stefano Ferrara. He's an investor, go to market advisor to countless SAS companies and revenue agencies across AMIA, tapping into 15 years plus of advisory and enterprise tech sales at companies like Gartner and Cisco. Most recently, uh, Stfano has founded Venture OS, uh, at get venture os.com. There's a plug for you, Stefano. An AI native operating system for solo builders, microsass operators, vibe coders. Um and uh it's it's here where he runs growth and operations. So previously at Gartner he led emerging markets a business development team across that region which is a very different kind of sales than Hunter is used to and in a lot of my experience which is PLG and I know recently you're really going deep on fremium and uh so I'm anxious to get into that as well. So Stfano welcome to outf fox and uh it's good to see you again.

>> Thank you. Thank you so much Matt. It's a pleasure to be here with you. So to get to the point here, there's an interesting balance of experience. So I've spent a lot of my time in premium and then I've in many cases I've had to layer in salesled or enterprise sales into a productled growth or premium environment. You are kind of going the opposite direction. You've spent a lot of time in really consultative enterprise sales. Um I think if I remember right when I was researching uh the the challenger sales model and methodology came up quite a bit which I've spent a lot of time with and so I'm I would really love to just like dive into the tensions around this because I know you've been thinking a lot about this. So like talk to me a little bit about specifically the tension that you you've seen companies experience who are trying to balance productled growth initiatives with a salesled growth initiative which both of which I think are challenging for people to figure out how to balance in exactly the right way. >> Absolutely. So I think we're coming kind of to a synthesis from two separate directions. And for me, you know, spending almost 15 years in B2B tech, sales and advisory where I learned and then taught the craft of prospecting. Um, you know, that was the bulk of my experience until very recently. And so for me, crafting short, compelling uh messages messages built on these three components of why you, why now, and a

clear call to action was always paramount in order to be able to get in front of a customer. And I believe that when this is done properly, it still works. But then in 2020, I sat in this revenue architecture course led by winning by design and that's where I met this gentleman uh Dave Boyce who was talking about PLG and who later wrote the book uh fremium as well about PLG and for me as a sales guy my first reaction to PLG was you know is it a threat to my career so I was both scared and curious at the same time. Um and I decided to go deeper and nowadays I can see it clearly that PLG and SLG they do not uh they're not rivals you know they actually are stages and where PLG earns you the meeting then SLG tends to close the deal. It's an interesting perspective where you're thinking of PLG as more of like a stage or a phase of the sales process and that the sales process is still critical to, you know, getting deals over the line, getting customers over the line, but and I I love this perspective because in my experience, one of the challenges or to build on your comment about did you see it as the enemy or a disruptor to you? I often find that at some point at scale enterprise organizations or sales-led organizations and productled organizations tend to create tend to find friction with one another because the best leads are entering in a very

warm state into the product directly. And so unless you instrument this experience correctly, you end up with sales folks saying, well, the best leads are in the product already and they're they're those go to account managers or something like that. So like I have found that in in various stage companies whether that's small um you know early stage kind of pre- series C or even in scale in publicly traded companies this friction exists. So how is like talk to me a little bit about this idea of framing PLG as a phase that also then leads to SLG and how that removes some of that friction. >> Sure. Absolutely. And by the way I don't disagree with you. I think that we are saying the same thing at the end of the day. Um, also because SLG has been the de facto way of selling into large uh customers most of the time and also uh in midsize organizations. Um so and also David Dave Boyce himself when he speaks about an organization looking into PLG and whether it's a good fit for them when they're an SLG organization he suggests to take it slow to invest about 3 years of time resources and effort and craft a task force within the organization that will build that out for one specific product in order to then make it a productled growth.

Many founders or many organizations that I've also come across um in my career think that just taking a product and offering maybe some subset of it for free means doing PLG, but that's not really the case. We've seen PLG emerge more into um B2C solutions u most of the time but we're seeing this now going into the B2B and also larger sales uh deals and organizations as you mentioned earlier. So Dave also speaks about that in in his book where he mentions that in some of these multi-billion dollar organizations who are adopting PLG the sales team actually is not even allowed to contact the customers who are already using uh the product even if it's a larger deployment but this is all handled then by to your point the account management or the customer success team. So the two can coexist and there are sometimes some very clear swim lane swim lanes there. >> Interesting. So in this model like do you think it really comes down to the size of the organizations that you're targeting as customers where you know cuz like one of the things that comes up for me as I'm talking to customers of various sizes. I still see that big organizations are often uncomfortable with productled growth. >> They don't seem to adopt technology that way. And so the idea that most of these enterprise or even larger mid-size organizations, the the experience I've seen them go through is one where PLG is

interesting to them, but it still doesn't totally align with how they buy. And showing people that this is self-s serve and they can just do it. They don't need to come to me or come to a sales or an account manager is still a bit foreign. Do you have you seen that as well? >> Absolutely. and especially in the Middle East where rapport, relationship, trust are a [snorts] strong element of any relationship between a buyer and a supplier. So, um I think in generally in general across the board this still applies to highly regulated um environment or organizations to what we might call also you know the dinosaurs, the old style companies who are used doing uh you know buying purchasing software or technology a certain way with very tight um procurement processes and steps that involve RFI. eyes, RFPs, selection, and basically the whole uh dog and pony show, right? Um and also if the buyer himself and the user is somebody in the organization that legitimately cannot purchase um you know based on PLG alone after using the product like a CISO for example because of the many implications that that would have maybe a little bit about the Middle East as well and where the trust components comes into the picture because that's where I had direct personal experience for the past 11 years that I have been living and

working in Dubai. buy and working across the emerging markets. So here as well sometimes if you are offering a product for free this is perceived as you're not being serious right. So there needs to be a handholding between having a product experience maybe as you know PLG or there is a um POV running a proof of value or a proof of uh uh concept running but then all of this needs to be always backed by a trustbased relationship between the seller and the buyer. I'll give an example. U in my days at App Dynamics, uh which has then been purchased by Cisco, um I was the second salesperson on the ground in Dubai covering the Middle East. And ABD's uh playbook at the time said that you must touch every advanced opportunity twice a week with an in-person uh meeting with a prospect, no questions asked. And so in my efforts to apply the process by the book, I would make up reasons to show up at the client's office. And uh I did this one too many times with a VP, an Amirati gentleman in one of the larger largest telos in the region until he basically started screaming at me across the open floor and uh I had to leave uh

embarrassed and uh you know obviously the deal then sold because I hadn't earned the right and the trust to show up and to bring more value. it was a stage where they were now huddling internally in order to come up with a decision and an extra touch point from the sales guy was really not needed. So obviously I say this story to the startups I advise and to the teams also that I managed because this shows how it's important in taking the playbooks that might emerge from Silicon Valley SLG and PLG alike and then you need to actually uh make sure that the reality on the ground and the trust is there wherever such requirements are needed and believe me in such a large deal and large customer that uh I spoke about it was definitely needed. >> What's interesting here is the number of touches that needed to be in person. You know, so much of what we do in software is virtual now or is remote to the fact that it almost feels strange to get on a plane and go somewhere and meet someone face to face like it feels a little foreign. Do you also find that that is true or do you find like in the Middle East for example the opposite is true where in fact they expect some sort of in-person or kind of more face-toface experiences? I find that uh despite the covid days uh democratizing

virtual meetings and zoom calls or Microsoft teams meetings even in the Middle East there is still a preference to having in-person meetings especially for the meetings that matter like big negotiations, board presentations and also in bringing in the more senior person uh in the organization that still has a weight. We're often taught in B2B sales um that you are the CEO of your own patch of your own business. So, it's down to you to go from prospecting to booking the meetings to conducting the sales cycles and closing them. However, in the Middle East, there is still this um attraction and this proclivity by the buyers to want to see the senior person in the organization. So, if I'm dealing with a general manager or a CEO, they would expect that sooner or later they will see my own general manager, VP, senior person or even CEO. And that's probably why you're seeing the big CEOs of the large tech giants like Sasha Nadella or Chuck Robbins at Cisco and many others taking trips from time to time to Saudi Arabia, to the UAE to meet customers in person because that's still

very much needed in order to show them that we care about you and that you are important to us. >> Yeah, that makes a lot of sense. Now, this all makes sense if you're dealing with large deals, large businesses, um especially if you're dealing with atscale software products, but you started your own, right? You have your your own business now, Venture OS. I have to imagine there are some differences that you're finding as you take as you do the go to market for that business. >> Absolutely. Um so many differences because venture OS is uh targeted to um startup founders, vibe coders, micro SAS um and these individuals are usually younger and they are most of the times techsavvy themselves already and used to purchasing after having used a product which [clears throat] is uh has productled growth in it. I was I wrapped up my um enterprise career in the corporate world with Gartner in June of last year and I decided that I needed a break and to decompress from the past 15 or so years in the corporate world. So I took my wife and daughter and we went on a 8-week trip across Europe. When we came back to Dubai, I took the remainder of 2025 as a sabbatical where so many of the interests, hobbies, and bucket list items that I never had the material time

to actually do when you're working 10, 12, sometimes even 16 hours a day for a decade plus. And so I got that out of my system. And as part of that, I also went back and met with so many interesting people from either my professional past or that I always looked up to and I, you know, reached out just to say, "Hey, I'm on a sabbatical. I would love to buy you a coffee and get to know your perspective on life, on things." And so many people accepted that. Perhaps also because it's not every day that you find somebody on a sbatical. Um, you know, I've heard many times the comment that it takes a little bit of courage to kind of step out of the uh safety also of, you know, paycheck or a salary and then do this without knowing what comes after. Um, but I knew that that something that would come after would happen naturally if I just let things take their natural direction. And so in mid January of this year u a former colleague tapadinas who used to be uh one of our VP research analysts at Gartner in the space of data and a AI and analytics. He reached out to me and he already had a third co-founder lined up and offered for me to join them and start what became venture OS. So I found myself from leading a team of corporate

B2B salespeople to being the COO and head of growth at this startup designed for vibe coders and people who have an idea and want to ground it and make it a uh make it come true basically or who have a nice GitHub repo have a bunch of nice uh little lovable projects or you know bitecoded with some of the other tools out there and then they're wondering What would it take for me to make this into a business? What would it take for me to actually start getting paying customers? And so to turn my little repo into actually a thriving business. There are a number of ways you can uh you can go about it. One would be you hire some fractional people. Another could be you would find the business co-founder, which is what my two guys did. Another way could be going with a marketing agency. you could also stitch up together a bunch of solutions. And obviously all of this would come at a higher cost or you know higher amount of time and stress I would guess. And so we decided to take all of this and with the power of AI we were able to go from first idea to releasing the MVP within the span of 3 months. By midappril we launched our MVP. Two to three weeks later we had a couple hundred users organically. um basically converging into the platform and uh um really every principle that I am applying to venture

OS is based on PLG and on premium. I want them to have this unbound experience that delivers first value. I want them to be able to experience it before they even basically uh sign in or create a profile so that they can get some tangible value in exchange for that first login. and then obviously creating the right experiences and the right gates if you like to um the paid experience of the product at a later stage. That part often is the hardest figuring out where to draw the lines so that your free users are really also leads and then also figuring out where to draw those thresholds on conversion or uh put putting them into sort of a paid a paid plan. Um, how did you choose where to draw the lines initially and did that work? >> Absolutely. And this also came not just by us but also by putting you know the MVP out there quickly what today is being called as building in public so that we would actually get guidance from the actual user base as to what to do next. And so the first decision that we took within probably a week or so was not to force people to uh sign up at the very beginning but to open their on boarding experience just as a guest and then they would get um to the first

deliverable which is you basically put in your idea into venture OS into the tool. You have the team of AI executives starting to analyze this idea, asking you some follow-up questions and building for you two main deliverables. You would get a competitive landscape and you would get an idea assessment brief. And so these two first deliverables is where we would place the gate of going from guest to now you would basically sign up. We showed you some goodwill and we delivered to you tangible value by making something for you that can bring you a step closer to make your idea come true. In exchange now you can continue using the platform and we would show basically what we call a venture map which is how far you can go within venture OS if you were to continue using it. taking it from idea to actually a product and then in into basically a product that grows an audience, a user base and obviously revenue as well and potentially fund raise and obviously much more than that.

So that was the first the first step. >> How well is that working? >> It's been working great. We saw, you know, skyrocketing the number of users who would actually go in and who would then leave their basically credentials by creating a profile. And now the next step is where do we place the uh paid gates basically. And so for instance, if you want to work on multiple ideas, there would be a gate there where okay, you can work on one idea, but then if you want to work on more ideas, that's where you would basically come into one of the paid tiers. Or if you want a certain subset of this expertise to be delivered to a bigger number of individuals, maybe it's not just you, maybe you have a team, you're a microsass, then you would also basically um have a paid tier for that. And to be honest with you, we are still figuring it out at this stage and we do not want to um hasten any decision before we have the data points. But what I know for certain is that I want to give that experience, that aha moment to the user when they start using it. And I want to make sure that I can reciprocate that trust so that when they become a paid user, they know what they're in for and what they can expect by basically rewarding us with their hard-earned money. Has this been natural for you to

try to think about a goto market motion that is more like the product selling itself as opposed to using tools to funnel opportunities into sales reps to get them over the line? Cuz like this is really removing sales from the process more so than instrumenting it into it. Was does this feel like it's coming naturally to you or is there like do you find some internal sort of mental friction that uh you know from your past where you're finding it not feeling completely natural? It definitely is not completely natural and uh sometimes I catch myself defaulting back to crafting my own outreach onetoone maybe to specific people that I want to try it and so I go back into sales hunter mode myself but I know that this will only be the small minority of cases where I can count on my network to go in try it out and then become a long-term user. the m the vast majority of that will come organically by users who come across the product and start using it and then they get hooked into it and they start extracting value before they even start paying for it. So definitely that's the hard uh harder part for me right now. But I am you know educating myself a lot. I am obviously listening to u podcasts like yours that

is giving me a lot. I am reading a a lot of resources like Dave Boyce's book fremium that we already mentioned. There is also this uh interesting uh um newsletter from a gentleman called Kyle Pyer and uh he also speaks about um how uh you know out of a thousand uh basically users you can get 5.6 on average paid customers if you do not gate the experience and you let them explore it without even asking them to sign up just yet versus only 3.6 six if it's more of a a demo or a kind of a closed trial for the product itself. So I am a numbers guy at the end of the day and I'm a very rational guy and so I trust the research that is being done to be working and I try to apply as much of it as possible since I do not come with any legacy with venture OS versus some of the large organizations maybe trying to retcon uh PLG into their existing motions and processes and you know that's where perhaps it's trickier than just you know leaprogging and starting from scratch Boy, you hit the nail on the head with one of my biggest pet peeves. I've I can't tell you how many times I've either consulted or just inside organizations have had conversations where a leader or the CEO, whoever comes in and says, "Hey, I think we should bolt on fremium. Uh what should we make free? Like, how do we

make something free? Uh is a free trial good enough?" Um what's your opinion on this? I I'm I'm really interested to hear your thoughts about how would you give people guidance about incorporating a PLG or a premium motion into their go to market. >> Yes. Um definitely it's not as easy as okay let's you know let's take this product and then you know give a bunch of it for free and then you know gate it from here on out. That is to me more of a ticking uh you know the box type of exercise. um which could be dictated by the board asked us to do PLG but obviously then the results would not come and uh this is also something that comes up a lot in my experience advising some of the tech startups out there and u uh I would say first of all it really depends on the product what it is what it does how are the current workflows and ways in which the customer extracts value. Second, which actually should be first I guess in order would be the customer itself. You cannot just apply a PLG motion to any type of ICP and to any type of buyer out there. So that also needs to be u needs to be researched. And I would say also there is a big shift that need to happen to your earlier point when it comes to the sales

force itself. It needs to be clearly communicated and structured so that SLG and PLG do not conflict with each other but they go hand in hand. There are instances in which they might strengthen each other, but there will also be swim lanes to avoid uh funny stuff probably happening because we are salespeople and we know salespeople and we know that sometimes we're looking for you know the shortest trajectory to reach an outcome and perhaps having this customer you know or this prospect using now the premium solution is seen as a way for me to jump in and then still you know uh vomit onto the customer this big playbook uh that we've been applying and you know it will mess up the relationship rather than improve it. >> I find that um you know my personal experience with sales teams and PLG sort of trying to work together is that often a company has to make a choice and they have to make sure the business is instrumented around that choice and that choice is whether or not sales is leading or productled growth is leading. Do you want fremium to be the real driver of your funnel or is it really just a lead engine? And I feel like like I I've tried to articulate this different ways. The way I would describe it sometimes is like you have to choose 60/40 one way or the other. It doesn't you can't do 50/50. 50/50 is going to create conflicts. You have to choose

6040. You can either be 60/40 sales or 6040 premium, but you can't just perfectly strike the balance on both. Um do you think that's right? Do you like do you think that that's a good way to describe it or do you think that that trivializes it too much? >> I think it's definitely a great rule of thumb and a great starting point. There will always be nuances and there will always be use cases in which you know it's more uh than 60 on one side or the other. Uh but definitely you know if anybody needs to start from somewhere knowing that there will be constant friction if the two have equal weight um is something that they need to make peace with at the very beginning of their PLG journey. Today's episode is brought to you by hunter.io the B2B lead generation platform made for every professional. Whether it's prospecting, fundraising, recruiting, link building, or just trying to connect with the right people, Hunter makes it easy. >> You know, you mentioned the word trust a couple of times. I want to I want to circle back to this because one of the things that I have heard customers say to me in like just conversations or prospects say to me is, I really am impressed that you guys just make let the product sell itself. you know that you that you make a free product available that's that is I mean it's limited but it still has the majority of the critical functionality to evaluate the tool and you have access to real data it it creates trust is essentially what they've said um but

sometimes that's not the case right like if I were to I think go into some enterprises and tried to say oh yeah just sign up just do this directly you know do it by yourself that doesn't instill trust in the same way so this kind of gets back to what you were thing a little bit is it starts with the customer. What does the customer uh like? Um [clears throat] but I guess like fundamental to that is figuring out how your customer needs you to develop trust. Is that is is that kind of the way you think about it as well? >> Absolutely. And I think you know probably before you can start building trust you want to learn what trust means for that specific customer. And uh you know I definitely am the kind of customer that if you give me a limited doree um experience with the product and I see it solves real u you know problems I have or give me real value that builds trust and I know that down the line I will be willing or I am willing to pay for that. Um I have a few examples on my mind right now. One is granola. Uh I have been, you know, a free a free user of granola for a while, but I already know that one day I will need that critical piece of info that was saved more than 30 days ago. And so I'll be unlocking the paid version so I can go and I can basically use all of the uh insights from the conversations that

Granola has been a part of. Or another one is Posthog. Uh Post Hog as well. Um, you know, I've I'm on the free version still now with Venture OS, but I've already mentioned it to three other startups who have gone on and signed up also with the free version. But, you know, they have an advocate in me without even knowing it because of how much value it's been delivering. And you know eventually as we grow uh our u relationship with postcog will probably grow as well and we might be willing to uh or will be willing to to pay for that as well. But in some other contexts and some other um situations where you have a large enterprise customer trust will be what we also spoke about earlier which is you catching a plane or driving uh you know down to see them even if it's a couple of hours away. um to have that in-person, you know, off thereord chat. Um and yes, this resonates in some cultures more than others, but being Italian myself, uh somebody taking the time to actually, you know, park on the side the business talk and just, you know, grabbing a coffee and, you know, asking me more about myself, my interests, my family, whatever. uh and me also learning that about them makes that much more relatable. Um and this is probably you know something that in the B2B uh sales world you would want to

build that relationship uh uh with the individual and even many years later they would still remember you fondly and you would remember them fondly even after the deal took place or it didn't to take place for whatever reason but there is still that you know good feeling about that individual um that carries across organizations. I guess and transcends. So there are two elements and probably in the PLG world what used to be true which is somebody needs to trust the product the brand and the person i.e. the seller. You know this is much more skewed towards the product itself. So it's almost like a balance of depending on the organization or the customer determines how much of the emphasis for trust needs to be placed on the product, the company or the individual. It's almost like a you're you're doing trade-offs. Well, if you're a brand new company, that doesn't establish any trust. So you have to overcompensate with the people and the tech. And so if you're a solo entrepreneur or a vibe coder and you're trying to do this, you don't have the company credibility or the individual. So, you have to use the product to establish that trust. That's kind of an interesting way. I've never quite thought about it like that, but I I like this idea. It's like you only get so many levers to pull to create trust. And so, depending on how which levers you can pull determines how much you have to pour into the others. Yeah, I really I

liked that framing. I think that's really a practical way to think about it. That's good advice. >> I know you've worked with agencies. This is a really curious thing because I've certainly thought about this over the years and I think most people in agencies or people who work as independent agencies I guess would bulk at the idea or push back at the idea of giving away something for free. So, how do you advise agencies around PLG and um like if if we have agencies listening, which I'm sure we will, what is some advice, some like practical advice you would give them about how to think about PLG in an agency world? >> Sure. It's a quite an interesting question and uh what I've seen in recent years is the emergence of the concept of services as software which is something that um with the advent of AI uh has become you know popularized and feasible I would say doable compared to uh before and you know agencies or services businesses they notoriously wouldn't be at first glance a fit for PLG because they do not have a subset of a product that maybe they can do for free and offering a bunch of bespoke or customer services beyond maybe the um the customary hey let's book a 30inut free consultation would not be scalable for them. Um but definitely now in the days

of uh services as software it's definitely doable and uh you can definitely think of tools like Harvey for example which is this uh um basically law based uh solution AI solution that is drafting the legal drafts for PWC for example and uh you would therefore have u small pieces of work delivered as the outcome itself to the customer for free. And that would be the the PLG motion if you like. And then if the customer wants more deliverables, if they want more outcomes, then they would be looking to engage in you know a paid engagement and therefore take it forward directly with you know a salesperson within the agency in order to evaluate how we can then scale this one piece of deliverable further beyond that. >> Yeah, that's a good good advice. It also gets me to my next question which perfect pivot great transition. Obviously, we care and think about uh outreach a lot. Uh that's the primary focus at Hunter. Um and I'm sure you've been on the receiving end of a million different kinds of pitches. Um certainly I have as well. When you talked about the audit or you know the assessment, that was one of the first things that comes to mind. I get a ton of free audit, free assessment emails. Are you doing cold outreach? And if so, how well is that working for you right now? Right now I I am not doing a cold outreach for

venture OS on purpose uh because I wanted to be grounded in uh PLG and premium principles. I'm doing warm outreach to people within my network on LinkedIn or elsewhere who might be instrumental potentially for that word of mouth part of growth within the organization. However, I am doing cold outreach with some of the startups that I'm advising which are still B2B S salesled kind of focused mostly and um I am definitely on the receiving end of a lot of uh cold outreach as well and what I found very interesting u you know going through also your state of outreach uh 2026 report was how there is a general preference um to being reached through LinkedIn versus email, right?

It's a flip compared to 5 years ago. Uh 65% if I remember correctly of individuals said that they prefer being uh basically uh connected with via LinkedIn than via email and only 25% still prefer email nowadays. And uh there was also a preference towards smaller cohorts of batches basically of emails being sent out where these are much more effective. And to me the why you why now and a call to action is still the golden rule. In fact um the CEO at curvo.ai AI which is a real-time sales uh intelligence platform which I ended up investing in as an angel and also becoming an adviser to was one of the best uh sales outreach cold outreaches that I received uh in the last couple of years and that worked on me like a charm. But equally there are so many that are really bad. you get laundry lists of services, sir, we can do this for you and that for you or uh you know easily avoidable typos where the name of the previous prospect is you know there where my name was supposed to be and so I think it doesn't take too much to really fix up some of these things and do that you know 10% of research that you would need in order to get somebody to pay attention to your message and then to answer and give you

a meeting out cold. I was thinking a bit about this as well and like by the way LinkedIn versus email is a variable that's I think mostly based on which one is getting more volume at the moment and in the past LinkedIn has sort of enabled a lot of outreach on the platform and I find that when that's true when they're really pushing doing outreach on the platform preferences tend to shift and then when email gets really heavy preferences tend to shift towards the other way around. But honestly, at the end of the day, there's only so many channels. So, honest, you should be using them both. You should use them all. You should use retargeting. Uh if you really want to do this, I don't think that they're mutually exclusive with premium. to your point about you know email LinkedIn um yes I think even in the B2B uh salesled uh days you know we are taught and and you know we then also teach our uh you know our teams to use a multi-channel approach right so it might be email today LinkedIn tomorrow a cold call as well which nowadays especially the younger generations it's very rare to find somebody who would really pick up the phone and call. I will admit that I am uh you know not the person who loves cold call the most myself. If I were to do it, I would tend to default to crafting some very compelling outreach messages and seeing this getting replied to rather than you

know picking up the phone um and uh and doing volumes of that. Um but we can also see this how uh it's a generational shift a bit because the boomers are now you know phasing out of the workforce as well and this is probably also why um PLG is picking up at this specific moment in time. Millennials Gen Z they love to tinker more to educate themselves before they ever come across a salesperson. And actually Gartner's research says that 83% of the time is spent by the buyer on their own researching, learning, experimenting, you know, download downloading that uh uh, you know, trial or that free version of the product. And only 17% of that time is spent with a seller or with all of the sellers combined for that specific uh buying decision. And so each individual seller sees a much smaller chunk of of time from the buyer. And so I think that that's also a big a big drive towards ELG and towards self-service more than ever before. Yeah. This really started with Gen X who were leaning away from traditional outreach methods. And I think especially like I'll use myself as an example. I had to do cold calls when I first started in my career. And I think part of the reason I've been so focused on technology ever since is because I would like to eliminate that from everybody's

diet. If I could like have like one mission that I could somehow accomplish before I go I would love to help cuz I you know my first product was chat and then you know I worked on chat from a an AI perspective uh just before chat GPT came out now cold email. I'm basically trying to make every communication channel better uh so that we don't have to rely on cold calls. Uh, but you're right. I think millennials, Gen Z, we are trending farther and farther away from those being effective. And the more technically native you get, the less likely you are to accept one of those calls. So, as I'm sure you know, you've talked to sales folks and you've talked to people who just think that that's still the best method. Do you have any data to suggest that it's still effective? Even if you don't personally like it or believe in it, have you seen data that suggests that it still works? it does I would say more you know anecdotally than datadriven and at least you know in in the Middle East I would say um based on my experience of again combining a different number of outreaches so sometimes you know coming finding somebody's email address or having them reply to a LinkedIn message is very hard whereas if you just you know call them u give them a cold call because is maybe so such a rare method nowadays they would tend to pick up the phone more. So even there I think it's a matter also of volumes as you were saying earlier between LinkedIn

and email. I can see that a little bit but I would also say that um you know if I use myself personally and it also varies by the industry but for instance the real estate industry in Dubai it's right now um well obviously with the current situation it kind of died down a bit the whole buzz around real estate but the last couple of years have been just manic. If uh you had a property and it ended up on some your number ended up on some you know list it would be shared with every and any of the 48,000 sales agents that we have uh in Dubai and uh there's nothing nothing like you know GDPR or you know data privacy is like your number gets out there and then you are a free-for-all and the number of calls I'm getting to this day you know I had a property which I sold two years ago It's multiple calls a day to the point that I've stopped picking up any call who like that I don't know who is on the other side and what I say to myself and the way I like to be if you like prospected or contacted is if this is something really important and this person really wants to talk to me you know they've gone to the lengths of cold calling me I haven't picked up they will drop me maybe a WhatsApp message or a text that I can read and I can decide whether I want to have any further engagement and it's sub 5% probably the number of people who follow the missed

call with a WhatsApp message and you know that's where I at least take it one level further to then assess whether this is worth my time or not. Well, there you go listeners that's a good trick to uh how to use multi- channelannel to actually be effective. And actually, what I like about what you're saying though is you're almost it's almost like if they make the effort to make the call, that gives you a little bit of awareness of them, but if they but but not because you want to take the call because you're kind of looking to see how else they follow up to because you still want control over that situation. Yeah, I like that. I think that's a good that's one of the best arguments for still doing cold calls I've heard yet. So, thank you for that, Stefano. >> Sure. >> New segment here on Outf Fox. What uh what I would love to do with you, Stefano, is let's have you take a look at an actual email that uh that someone has received and I want you to look at this as a person who receives outreach and tell me what do you like, what do you not like. Just pretend this person doesn't have feelings and uh okay and go ahead and and give your breakdown or your tear down of this particular email. So the email says uh made this for Hunter. So that's the subject line. Hey James, we checked out your site and put together a custom strategy doc for Hunter. It walks through how to find and reach sales and marketing managers who need an email outreach platform right now. Your beautiful company logos even on it. We've built these systems for

other companies and booked well over a thousand meetings generating 2 million in revenue. Want us to send it across? So first things first, would you have replied to this outreach? probably not. Um to me it would probably be an instant delete for two reasons. One is more subjective and one is more objective. The subjective reason is the lowercase M in made this for Hunter in the subject. And you know I'm very detail oriented and if you didn't even go to the length of making sure that you proofread and that you write things properly that for me can be a disqualifier in and of itself. But even if we look beyond that, the meta here is is like these guys are, you know, expecting to sell email outreach to Hunter. It's like giving SEO advice to Google. Maybe if they done a little bit more of of, you know, research, actual research before sending this out, they would have avoided themselves, you know, some some shame and, you know, probably another delete uh that would that would uh, you know, be rightfully deserved. So this would be my kind of initial observation. But you know then if we keep reading further the fact that they say we've even put your beautiful logo on it sounds to me like that's the only piece of customization that they've done uh which is to put the logo rather than than anything else.

Definitely they do not know or they have downplayed the fact that basically Hunter does uh sales outreach right and email outreach in the first place. So these couple of things for me would be these qualifiers. Then they are using um you know they're throwing some numbers there you know thousand meetings 2 million plus okay but from where is this grounded in some research you know where where are these data points um coming from um so this would be the the areas that to me would uh would basically disqualify it. It's no customization, you know, it's no research really and the only thing that they did is to put the logo on um and expecting me to what to want to see this uh this report that you have allegedly built. Sounds sus to use a jenzi expression. >> I agree it does. And you're right. Like one of the things that drives me crazy on this is they haven't really taken the time to demonstrate that there was really any thought put into this because we checked your site and put together a custom strategy doc for Hunter. Well, you can use a variable and swap that out with a simple trick and then suddenly it's quote unquote personalized. But you haven't actually put anything in here that indicates that you did actually learn anything custom to me. So, like if you put together a custom strategy doc, wouldn't you reference something from it? Wouldn't you want to do more than just put your company's logo? And also, like you're saying that your beautiful

company's logo is even on it as if somehow that's a really difficult thing to accomplish. [laughter] Like, I don't know. Yeah, it just feels like there's no real meat on this uh on this email. And uh I think I get two a day uh from people trying to sell outreach services to Hunter, which I think is just hysterical. But uh >> well you could have uh taken the approach of okay let me take the meeting and see whether there's anything these guys are doing that you know we might learn from if the outreach email was better as we said earlier but you know in this stage I don't think that there was any point even in doing uh some competitive you know scouting or intelligence >> agreed subject is Stefano question [clears throat] mark Stefano When you find a winning angle and try to scale, what actually slows you down? Colon A. Two to three weeks to warm new infras.

B. Inboxes getting flagged mid campaign. C. Constantly rebuilding your sender infra. We fixed this. Pre-warmed Google workspaces. In workspace inboxes, 45 days, ready to plug in to instantly or smart lead in approximately 30 minutes. If one gets flagged, we replace it. Worth comparing to how you're set up now. O, so this is one you've actually received. >> Yes. And three more follow-ups after this. [laughter] >> So, okay. So, let me uh let me take a crack at this one. The first is when you find a winning angle and try to scale, what actually slows you down? Colon. Okay. First off, terrible intro. What are we talking about? when you find a winning angle to what and try to scale it, how what actually slows you down. Is that a question or a statement? And then if it's like is it a question? Because then you're giving options. So is it multiple choice? Like what if my answer isn't on the multiple choice? I'm now at two to three week to worm new infras.

Still have no idea what we're talking about. Inboxes getting flagged mid campaign. What kind of inboxes? What is this about? I'm now one, two, three sentences effectively into this. still have no idea what it's about. The subject doesn't tell me, which by the way, I think is terrible. Are you asking if I'm Stfano or are you saying Stfano, I've got a question for you, and if so, couldn't you have said that? I don't know. It's just terrible. Um, constantly [clears throat] rebuilding your sender infra. Okay, again, third choice in a multiple choice option, and I still don't know what you're doing. We fixed this. Oh, great. You fixed the thing. I still don't understand. And then you get to pre-warmed Google Workspace inboxes. Okay. So, what you're saying is A and B and C are actually all the same thing. And so, it doesn't really matter if I picked A, B, or C. You're saying what is actually slowing me down is one of these three things that you have fixed. O yeah. Okay. You should never get halfway through an email and still not know what it is, what it's about. This is terrible.

>> Yes, it took me about I had to read it five times before I even started understanding what it was, you know, why he sent it to me and what was I supposed to do with it. >> I'm guessing, Stefano, this was a hard delete as well. >> Well, absolutely. And so were, you know, the automated, you know, follow-ups that kept coming every few days, uh, I guess until the sequence on me was over. Uh but definitely yes, another example of how not to reach out to a uh prospect in a cold uh way. >> Yeah, I you know I think to answer my own question from earlier about whether or not I think that this is uh salvageable, I'm not sure. It's pretty bad. There's a lot of just editing that could happen here that would make it slightly better. And I know this whole thing about like not capitalizing things is somehow meant to demonstrate that a human wrote it, but like do you want to prove that an idiot human wrote it and can't spell or capitalize? Like like it feels like a weird pattern disruption that they're trying to use to try to make to try to accomplish something that I feel like they just wildly missed at.

I think the intro to me the intro just blows it. Like if you can't explain roughly in the intro why I should pay attention to anything else, that's it. I think the intro is just critically important and this one just blows it every which way I can think of. >> And Matt, this is the epitome of, you know, write it once and send it to everyone, right? There is no tiny bit of customization other than, you know, putting my name twice in the subject line and then, you know, in the in the body of the email. um like how is this going to be you know making me think okay this this person actually understands who I am what I'm doing what my issues are h or maybe they think that the problem that they are solving is so commonly felt by everyone that the same email uh would work for people >> yeah you're right it's it's you know it's interesting that is a pattern of both of the emails we've looked at so far that neither actually does an effective job of trying to make sure the email is relevant to the recipient like that alone who was just like the absolute base baseline table stakes requirement is failed by both. Yeah, good call. I am actually surprised that you know the spam filter uh of my Google uh space didn't automatically you know chug it in there that I was even able to see it and to see the follow-ups. So at least they were able to get that one thing right which is to pass the spam filter. But that's as far as they got.

>> And it's a good point because if this can get past the spam filter, even anybody making a reasonably good attempt at doing outreach should be able to get past the spam filter. So yeah, I think if anybody out there who's watching or listening is worried about whether or not their email is going to make through the spam filter, I think you can use the last two examples as really good evidence that it the bar is not that high. Um even though they're trying to optimize that in Google, I know for sure the bar is not that high. Yeah, this is uh that's a good one. This has been great, Stefano. Really appreciate your time today. Uh loved tearing the emails apart, although I hope it was productive for our listeners. It wasn't just there to bash people. The goal is to try to highlight the things that aren't working so you don't do them. So, I guess let's let's end with some advice for our listeners. Uh other podcasts in addition to Outfox that you uh would recommend to anybody who's listening today? >> Sure. I would definitely recommend the product market feed show. Um that's um something I found towards the end of last year and I have been addicted ever since. Especially I believe the audience of outf fox would resonate with that a lot and PMF is probably a topic as big as PLG uh for many founders and individuals looking to you know build a repeatable and scalable uh revenue machine out of their organization. Other than that, probably the usual suspects,

Diary of a CEO, uh, Modern Wisdom, and, you know, some of these other news shows that keep me current with what's happening out there in the world. That's great. Well, listen, it's been a pleasure. If you are a founder, if you're vibe coding, if you're trying to build something and you're looking for a better way to try to make some decisions, I highly recommend check out VentureOS. Get venture os.com. Is that right? I guess right out the final e in venture. So it's venturos if you like from a spelling perspective. Get venturos.com. Um and uh thank you so much for the for the shout out there Matt. And yes, if you are Micros Vibe coding, you have a shortage of decision makers and individuals who will actually do some work. Venture OS will bring to you a team of AI executives. You will find a chief of staff in there, a COO, a CMO, a head of growth. You'll find a chief product and a chief technical officer, technology officer in there as well. And all of these are highly customized agents who know what a startup founder needs from the first idea to then building a product and then to transforming it into a company. We really would love to be part of uh Simultman's vision of uh thanks to AI there will be a new batch of uh unicorns

made by only one human and so we believe uh that venture OS plus the individual walking into the platform can and should one day become a unicorn organization and who knows if there is also a path for us to become unicorns in uh in the way then uh we would love nothing but Well, good luck with it. I'll keep an eye out. Hopefully uh we can have you back and uh maybe join a webinar and we can dive in deep on uh Venture OS and how we can uh how we can potentially use it to help customers. So, I appreciate that. It was great to meet you, Stefano, and spend time with you today. >> Absolutely. Likewise, Matt. Thank you so much and looking forward to our next conversation. If you like what you heard, please like, subscribe, and explore even more of the Outfox community by visiting www.outfox.hunter. hunter.io