Sales, Marketing, Sumerians and Avoiding Founder's Disease!

Joining us today in the Sky Lounge is James Rozich, founder of Wheels Up Sales and Marketing. Jim specializes in helping early-stage startups overcome the unglamorous yet essential challenges of building solid sales and marketing processes. From CRM implementation to crafting value-driven email campaigns, Jim shares practical insights that founders need to create traction and scale effectively.

In this episode, we explore the realities of early-stage startup sales, common pitfalls, and the art of developing scalable processes that work. Jim also shares his thoughts on the evolving venture investing landscape and why startups are becoming the “new bricks and mortar.” Plus, we dive into the tools and tactics that can help founders thrive, including the strategic use of CRMs, leveraging AI for marketing, the critical importance of personalization in sales and how Sumerian checklists factor into Jim’s process!

ABOUT OUR GUEST

With a dynamic career spanning two decades in sales and marketing, I’m Jim Rozich. As an industry veteran, I have consistently navigated the intricacies of bringing products and services to market – honing my expertise in crafting tailored strategies for CRM implementation, devising lead generation tactics, and refining messages that resonate with target audiences. My genuine passion for business development and startups is what sets me apart. Embark on your journey with confidence, knowing that you have a trusted ally with a 20-year history of propelling businesses to new heights.

I'm looking at these customers. I'm doing research into them so that when I reach out to them, I know something about them. And I believe that I get higher value appointments. It's not about the quantity of appointments. It's about the quality of the people you're reaching.

JAMES'S TALES FROM THE SKY LOUNGE

Todd Merrill:

Hi, welcome to Tales from the Sky Lounge. It’s a podcast about business consulting and venture investing. We get out there in the world, we talk to people who are making it happen, and we get their stories. If you could like and subscribe, it really helps us get our message out there.

So, today’s guest in the Sky Lounge, Jim Rosich. Hey, Jim. How are you?

 

Jim Rozich:

I’m great. Good to see you, Todd.

 

Todd Merrill:

Thank you so much. Yeah.

 

Jim Rozich:

Thank you.

 

Todd Merrill:

Why don’t you tell us a little bit about yourself and what you’re working on?

 

Jim Rozich:

Well, I recently founded a consulting company for early-stage startups called Wheels Up Sales and Marketing. And the goal of this company, our mission, is to help early-stage founders get their products into the market via CRM implementation, email messaging, and lead generation.

What we see in the market is a lot of founders have great ideas, but they don’t have a sales background. So, they have a lot of misconceptions about CRM and marketing. They think that they’re just going to take a tool, send out thousands of emails, and magically, they’re going to become a unicorn. And it doesn’t really work that way. Anyone who’s founded a company such as yourself, I think, can attest to that.

 

Todd Merrill:

Absolutely

 

Jim Rozich:

So, what I do is I get in there early on and I help set up the actual, I call it the unglamorous part of a startup. The business processes, the sales processes to get their product, to get some traction, and understand what’s working and what isn’t working and fix that.

 

Todd Merrill:

Well, that’s awesome. And you’re doing the Lord’s work there with the early-stage folks. There’s very important work in the ecosystem to get fledgling companies off the ground. And sometimes it’s hard work and it’s unrewarded, but it’s very important to get these folks off the ground, get them going. So, you and I were talking the other night. We were at the CIGI awards, which is kind of a fun thing for early-stage angel investors, awards ceremony.

So, you know, dealing in the early stage is a unique skill set. It’s that kind of commando phase where, you know, it’s a little bit messy, it’s a little bit violent sometimes, but a lot of stuff is happening very quickly, you know, and you just got to get stuff done. What do you think the industry is right now in terms of early-stage investing? I know VC has had a down couple of years, but I think early-stage is definitely a different animal. What are you seeing out there in the world in terms of early-stage venture investing in people starting companies in general?

 

Jim Rozich:

So, two things that are going on. First of all, early-stage investing is certainly changing. The money is just not out there for people. You put it when we were talking about napkin ideas. You can’t go to an investor and say, I’ve got this great idea and they’ll give you $100,000, $200,000 to help get it off the ground. So, it becomes more incumbent on founders to find alternate parts of paths to financing, alternate accelerators, things like that. And that’s part one.

So, part two is the good news, is there are some alternates. So, we’re seeing, for instance, the State of Georgia that we’re most familiar with, has given great support to the startup community through such organizations as ATDC and Georgia Tech. So, they’re really stepping up. So, you are seeing individual states that are working to help advance causes, advance the startup environment.

I think looking forward, we’re going to see is that people themselves are going to start considering startup investing, angel investing, if you will, as a part of a diversified portfolio. We’re already seeing that with Bitcoin, right? There are people buying Bitcoin that never would have thought about buying something like that 5, 10 years ago. But they’re looking at it and saying, well, this could fit into my portfolio. I own some stocks and I own some, you know, a house or condo.

And so, I think going forward, you’re going to see a shift where people are going to say, well, you know, I can start investing in companies because what I believe is that startups are the new bricks and mortar shops of 100 years ago. It’s not to say bricks and mortar aren’t going to go away. We were told they were going to go away 50 years ago because of the Internet or, you know, 25 years ago, but they haven’t. But startups are the new bricks and mortar. So, you have an idea. The technology is there, you have a little bit of money, maybe get some friends and family money, and you can launch your idea.

And, you know, as we all know, startups kind of have the same profile in terms of failure rate as bricks and mortar shops, restaurants as well. So, it fits into the profile. So that’s what I think going forward. That’s the most interesting thing to me, is I think you’re going to see a big shift in just normal people that would never have thought of investing in a startup suddenly getting involved in this community.

 

Todd Merrill:

There’s a lot more $10,000 checks than there are million-dollar checks in any given city or any region. Yeah, so it’s something to think about, you know, democratization of the investments into these little companies. Not everybody is on the mid or late part of their career and has a really rich network of folks that have a little bit of extra money, particularly in that younger set. It’s hard to find that money. But I think also, it’s easier than ever to start a little company, a tech-enabled company. You can be an instant merchant at the end of the day with like a Shopify or WooCommerce or something like that, or Amazon.

You know, it’s super, super easy to get into business and it becomes kind of back to exactly what you’re talking about that fundamental like shopkeeper mentality, you know, small business. It’s the same. You don’t have to be a tech-savvy entrepreneur from Silicon Valley to start a nice little business on the web or using some of these fancy tools that are out there now for distribution through fulfillment centers and that kind of thing.

 

Jim Rozich:

Exactly. And let’s back up a little bit, too. Let’s go to what people are majoring in college. You know, I can’t speak for you, but when I attended college, I went to a Liberal Arts school. You had History. There weren’t a lot of choices, but now there’s entrepreneurship programs that are fascinating, where they have mentors, they have programs. There’s outside nonprofits, some of which you and I are familiar with that go into universities and even high schools and run entrepreneurship programs. So, kids are starting at an early age to get an idea of how to find a business. And when you do that, then it makes more attractive to be that entrepreneur. I should say it becomes less scary to become an entrepreneur.

 

Todd Merrill:

Yeah. Well, and then so, you know, I had a board member that used to tell me, like, you have to make stuff and you have to sell stuff and then the rest of it’s kind of details. Right? But you have to do those two things, you know. So, the make stuff, used to be you had to grind away and spend millions of dollars to get some software out the door, and then you could start to sell. I don’t think that’s true anymore.

You can hack out a piece of software pretty easy today or a lot quicker and cheaper than you used to be able to anyway. And then there’s physical goods that you can buy and sell. And then there’s services that’s a natural, easy thing to sell to get into business, like plumbers and electricians and bakeries used to be.

So, the sell stuff, you know, it all kind of comes back around to you, no matter what you have, you know, good or service, you have to sell it. So, what does that look like for somebody who kind of knows what the make stuff looks like? You know, they come to somebody like you and then they say, man, you know, I am not real sure how to go to market. We tried buying a list from some spammer, is an email list and it didn’t work. What do we do? Can you walk us through like what’s kind of your favorite playbook for that young entrepreneur that it’s got to make it, you know, make stuff kind of sort of covered and needs to go to market and develop that part of their business.

 

Jim Rozich:

Right. So, to me, it all boils down to creating value for the person that you’re selling it to. They have to see value. Why? Why do you buy something? You either buy something to solve a problem or you buy something to help improve your profitability. If you’re a business. If you’re like a B2B, if you’re selling a B2B product, then your buyers are either looking to make more money or they’re looking to solve a problem, which effectually is costing them money.

So, what value? The biggest mistake that I see with early-stage founders and, you know, I call it founder’s disease. The biggest mistake I see is that they go to market thinking that they go with a feature set. And you see this with salespeople. There are more and more salespeople entering the workforce every day, but they’re not getting the proper training on true sales methodology. And you can go back 2000 years, sales has not changed.

You have to provide a value. You have to understand what the customer’s problem is. You have to get permission from the customer to get to their problem. You can’t call someone up and say, you know, I’ve got this product. Tell me about your problems. They’re not going to tell you that.

So, you have to be able to talk to people and follow a methodology to uncover the issues that they’re trying to solve. And then hopefully your product matches some or all of those issues and then get across that value.

Too many founders go again with this feature set. I have this product and I’m working with one right now on this that uses this email that we all get in our inboxes every day. And emailing, I mean, let me also back up and say emailing is still the most cost-effective marketing channel. Cold emailing is the most cost-effective marketing channel for early-stage startups to get directly to customers, potential customers.

So, they’ll go to market and they don’t have any training. They’ve built this product. They love this product. It’s their child. They think it’s great. They think if you don’t buy this product, there’s something wrong with you. So, they send out a bunch of emails, and they start out with something like, hi, I’m so and so. I’m the founder of this and this. We do this and this. Here’s a bullet-point list of everything we do. I would love to show you a demo of my product.

So, you’re selling somebody right away from the very first minute they open the email and studies show that 70% of potential buyers are not buying today of their product. So, if they’re not in the market for exactly what you’re selling, then you have no chance. But they could be in the market for what you’re selling, except for you’re telling them all these features and they don’t see the benefits.

So, what I talk to them about is the value. And we also talk about who their buyer is. They’ll say, well, you know, I’ve got an HR tool. I want to sell to HR directors. So, they’ll go out and buy a list of HR directors and maybe engage with an AI platform and send thousands of emails. You know, it’s the spray and pray. And invariably, these lists are really sloppy. Again, we all get emails every day. I got one. Why don’t you sell me office furniture? Why are you contacting me?

 

Todd Merrill:

Yeah

 

Jim Rozich:

So, you know, do you want a list of credit card companies? So, you’re taking your life into your own hands. So, then what happens is they start selling. They start using these bad lists and then they start running into email deliverability issues where they can get turned off. So, it can all snowball. And in the meantime, they’re losing money. They’re not selling anything. So, my goal is to cut through all that and show them how to provide value in an email format in six sentences. So, I’m using that as a relative term. But, you know, I go to them and I say in six sentences. We’ve got to get permission to have a discovery call with this person. So how are you going to do that?

 

Todd Merrill:

Okay. Got to be brief into the point and ask for permission to then talk about the problems.

 

Jim Rozich:

Right. But in order to get to that point, this is the rub, is you have to build trust. They always say people buy from people they like, but how do you do that in an email? I say people buy from people that have some credibility, people buy from people that they trust. So how do you build trust in a six-sentence email? And the easiest way that I found and I called this value-based messaging is to cite a common industry problem. You want them to think that you’re not just another salesperson, that you actually know something about the industry. And the easiest way to do that is cite a common problem that your product conveniently solves.

So, you say, in this industry, there’s as you know, I love to start emails out with, as you know because now you’re putting them on the spot. Oh, I better know this. If they don’t know it, then they’re like, oh-oh, I got to find something out. If they do know that, then they say, hey, this guy knows something that we have some common ground. As you know, this X, Y, Z industry has this type of problem. Here at such and such company, we do this and this, you know, get into features. You just mentioned, you know, we’ve got a product that helps do this and this and this. Are you open to a brief conversation? That’s it. It’s non-threatening. You don’t sound …you’re not pounding. You’re not selling. You have nothing to sell at this point. You’re just trying to get a discovery call where you can then go into a little bit more depth and talk about the industry and hopefully, they’ll begin to trust you and begin to open up a little bit.

 

Todd Merrill:

Okay. Well, let’s kind of like expand that a little bit. Let’s talk about maybe a little bit before you start the email list and maybe a little what happens when you start to get these nibbles. Maybe before you do the email list, I kind of this working theory of founders. You know, you really need to be in that industry. And I think you hit it right in the head there. Like, you need to be credible with your target audience, with your client, prospective clients. And the easiest way, the most direct, authentic way to do that is actually be in the industry, have a bunch of friends, have experienced that pain for yourself.

You know, I love messaging like, hey, I was working at blah and just like you, and I experienced this problem and I couldn’t stand it anymore. So, I started this company to deal with that problem. And then now you’re both on the same side of the table going, yep, that’s definitely a problem. You know, I’ve got the solution. I would really love to get your feedback. You know, ask for money, get advice, ask for advice, get money twice. Pitbull, that’s a lyric, but, you know, so that first 10 customers, my working theory is you really have to be able to call people you know, and be able to put this in front of the first 10 people and close something anything with the first couple people, even before you get to email. You find that that’s true?

 

Jim Rozich:

Oh, yeah.

 

Todd Merrill:

And you like to get, you know.

 

Jim Rozich:

Yeah, this is more of a scaling idea, you know, presumably. I mean, it can go both ways. But the goal is to get your first couple of customers. It’s always do whatever you can to get your first couple of customers. But if you want to grow the company, you have to be able to scale.

 

Todd Merrill:

Right

 

Jim Rozich:

And you can’t be that hyper-personalized. You’re going to hire salespeople. They may not know the same about the industry as you do.

 

Todd Merrill:

Okay, so let’s push on that end of it. Right?

 

Jim Rozich:

Yeah

 

Todd Merrill:

So, you’ve got a couple and then you start to craft these messages. Does that message evolve as you get referenceable customers and then you now kind of understand the exact things to say to people? And then you begin to hire that first individual contributor sales role. Kind of walk us through kind of that progression as you see it.

 

Jim Rozich:

Well, I view that as more of a marketing once you start going larger scale marketing, once you hire a marketing person and start doing that type of referenceable customers. I know what you’re talking about. You’re like, hey, we solved this problem for X, Y, Z Company. And that’s fine. I think that that’s more, again, something that’s more of a marketing.

When you’re doing one-to-one cold calls or cold emails, I think all you’re trying to do is pique interest so that the person receiving it says this person might have something of value to me. I see value in having a 30-minute conversation with this person. I’m not sure what their value is, but it’s there might be something here for me to talk to them about. I’m not trying to solve their problems first off the bat. I don’t know what their problems are. They may not have that same problem that I’m referencing. So, that email, what I’m trying to create is literally curiosity and say, I’m interested in having a brief conversation, not a sales, I’m not pounding them. I’ve got nothing I’m trying to sell them at this point in time. I’m not trying to solve a problem.  

 

Todd Merrill:

Okay. Let’s talk about the scalability, right? So, you start to get traction and people are responding to the message and then you get more than a couple, you know, calendar invites per day. What does that scale up look like? What was your favorite kind of, you know, what processes do you like to put into place? You have to build new processes as you scale startups. What does the team look like and then kind of what’s the tech stac of that scale up? You know, what are those? What does that process look like for a young founder?

 

Jim Rozich:

Yeah. So now you’re kind of getting into RevOps. So, let’s face it, when you’re talking, as you said, you want to get your first 10 clients. Most companies aren’t built to scale when they first start out. These 10 first clients, you’re getting the white glove approach. You’re the CEO. You’re the first salesperson probably. You’re talking to them all the time. You’re asking them how to improve the product, and that’s great. But you couldn’t handle 100 new clients. You couldn’t service them. You couldn’t sell them.

So now you’re talking about RevOps. And it’s important to understand that RevOps is what it isn’t. It isn’t a tool. It isn’t a set of tools. It’s a methodology whereby you are using, you’re evaluating. You have your tech stack that is designed to all work in concert with your sales team, your marketing team, and your support team to generate data. And then that data, how you use that data determines if you’re either going to use it poorly or you’re going to use it well. And if you use it well, then you’re going to be successful. So that’s how you have to look at that, that whole scaling idea. You have to take a look at your business and say, how can I grow this? 

So, tech stack. Yeah. You have to have a CRM camp. You can start working off of. I know that’s where you’re going but I wanted to get that whole thing out there. There’s no one tool that makes up that makes up RevOps. And there are a bunch of tools, you have to be really careful that you don’t end up with too many tools. 

 

Todd Merrill:

Yes. As a CTO.

 

Jim Rozich:

I love tools.

 

Todd Merrill:

Yes. You can cut a lot of credit card recurring subscriptions in a hurry.

 

Jim Rozich:

I have them now.

 

Todd Merrill:

Right. Well, sure.

 

Jim Rozich:

Why am I paying $6 a month? What am I paying $6 a month for?

 

Todd Merrill:

Yeah. Right.

 

Jim Rozich:

They creep. And it happens to all of us. I’ve even seen tools that go through all your tools and tell you which tools aren’t being used and you can get rid of them.

 

Todd Merrill:

For $29.95 a month, right? Or $19.95.

 

Jim Rozich:

But if you’re a Fortune 500 company with thousands and thousands of tools, something like that makes a lot of sense. So, you have to look at where you are. So, you have to start with a CRM, in my opinion. And again, this takes us into a common misconception amongst founders, and that is that CRM is just a data repository for email accounts that you just dump a bunch of, you buy your list or what have you, you use your AI tool, scrub LinkedIn or whatever, and dump a bunch of leads in there and start emailing them. But it’s really so much more than that. It’s data organization that gives you the visualization of how to improve your business. One simple thing is you can track how many touches it takes to get that first discovery call. So, if it takes you 10 touches to get that first discovery call, then you know that you don’t want to do 6 touches.

 

Todd Merrill:

Better start touching people.

 

Jim Rozich:

Better start touching people, but you build your cadence 10 steps.

 

Todd Merrill:

Okay

 

Jim Rozich:

So then you put that in your CRM. Okay, I’ve engaged with Todd. I’ve sent him email. Number one. I’ve called him. Number two, I’ve sent him email. Number three, I’ve done this. You know, you build that within the CRM so you can now operate most efficiently. Most CRMs have what they call tasks where you just punch a couple buttons and your task is automated so you know when to touch the next every two or three days however that may be. So, it’s really easy to use a CRM to scale, even if you’re small, and cost effective. You don’t have to buy a really expensive, there are several that give you, if you’re really small, a free trial, granted that’s very limited, but it’s a start if you’re cash-strapped. 

 

Todd Merrill:

Yeah

 

Jim Rozich:

It’s better than a spreadsheet.

 

Todd Merrill:

I’m a big fan of do it manually until you are suffering and then automate and then you probably got a pretty good idea of what it should be over and over and over again. You have a favorite, you want to name names on technologies? You know, I’ve seen Zoho, Insightly. I’ve seen GoHighLevel. I’ve seen HubSpot, seen Salesforce. You know, it’s probably overkill for a startup, but maybe you get a good deal on these accelerators. They’re all good. Do you have a favorite one or do you have?

 

Jim Rozich:

Well, that’s the thing.

 

Todd Merrill:

Certain things you look for or how do you?

 

Jim Rozich:

I’m a HubSpot person.

 

Todd Merrill:

Okay

 

Jim Rozich:

I’m a HubSpot partner. I started using HubSpot many years ago, 10 years ago, maybe. And what impressed me about it was that it really was focused on improving the salesperson’s life. So, I got into this whole business because I ended up working in the startup world. I’d been in technology sales and I ended up working for a startup. And I really liked it. I got introduced to HubSpot and I thought, wow, this is really, really geared towards me, the salesperson. And it still maintains it. Now it’s a huge company. But when it was first starting out, if you were a startup, they deeply discount it. Great customer service. They still have very good customer service, but they’re a huge company now. Now they’re adding tools and expanding into all these other areas, which you have to do in order to grow. But I still feel that they’ve maintained a relevancy to the one-to-one salesperson that’s out there banging on doors, trying to make sales.

 

Todd Merrill:

Okay

 

Jim Rozich:

So I’m a fan of HubSpot, but Zoho is very good catching wind. As you said, Salesforce has gone in a direction. If you were to ask me what the best CRM is, I would say, well, you need to look at 20 or 30 CRMs and see what one fits what you’re trying to do in your business. There are CRMs that are specific to law firms, specific to life sciences, nonprofit. Well, Salesforce has a deal with nonprofits. But, you know, there is no one size fits all. But I would say that for a B2B SaaS startup, you couldn’t go wrong with HubSpot.

 

Todd Merrill:

Yeah, solid choice for sure.

 

Jim Rozich:

Spoken as a partner.

 

Todd Merrill:

Yeah. Well, I mean, you know, and I’m not a partner. I have no affiliation. But I’ve not seen any HubSpot stuff go sideways technically or mechanically. Yeah, I think it’s a very solid first choice for sure.

And then, you know, let’s talk about integrations, you know, emails, one channel, and they already certainly is going to go bang on LinkedIn and maybe some other social media type to outreach. How do you think about the cross channel or when you design that early funnel, you know, that 10 touches or 6 or however many it is? You know, if it’s all email, email, email, email, just a different number of days apart, that’s probably not as effective as if you had a blended, you know, a couple of email touches or an email and a LinkedIn outreach. And depending on what happens, do something else. How fancy do you get or how do you think about multi… you get carried away on channels that don’t matter. We can talk about analytics in a second, maybe. How do you think about building those early funnels?

 

Jim Rozich:

So, this boils down to very early in the process. You determine, number one, who’s your ideal customer profile, right? Who are we selling this to? Is this something for Fortune 500 companies? I don’t sell the Fortune 500 companies. Is this something that I sell to startups? What’s the ideal customer profile? How big are they? What’s the revenue? And then within that, who’s the buyer? And within that, what channels are the buyers on? So, it’s really where can I find this buyer? If you’re a B2C, then you have to be on Instagram. You may not have to be on Facebook, but you may have to be on Instagram.

 

Todd Merrill:

…or TikTok

 

Jim Rozich:

You have to be on TikTok.

 

Todd Merrill:

Yes, sir.

 

Jim Rozich:

So, you have to take a look. This is of critical importance. Where do your buyers spend their time?

 

Todd Merrill:

Okay

 

Jim Rozich:

For what I’m doing for B2B, I’m on LinkedIn mostly. I’m actually moving more towards LinkedIn. I’m finding the last couple of years, LinkedIn is becoming an increasingly important channel for B2B, whereas people before just viewed it as, well, you know, I’ve got my thing, my profile out there, and whatever happens happens. But now there’s more and more marketing on LinkedIn, and it’s more acceptable. People will communicate with you on LinkedIn, whereas they may not communicate with you via email. So going back and forth, I think it’s very important and useful in that relevance. But again, as I said, where is your buyer spending their time? And that’s where you need to be. And that’s what medium you then need to master. Don’t try to master five different channels. You can’t. You’ll end up doing most of them average.

 

Todd Merrill:

Right

 

Jim Rozich:

Find the two, the one or two where they really are and then concentrate on that.

 

Todd Merrill:

Yeah. You know, kind of reflecting on something you said earlier in the context of LinkedIn, you get how do I know these people? And then who is this turkey that’s trying to reach out to me? Before I even engage with you, I’ve now been provided with that context of who is this and then how credible do I find them. Right? And then if I open it up and you’ve got a pretty good track record of companies I recognize and, you know, we know 50 people in common, you know, okay, I’m going to take that a lot more seriously than some, you know, Bozo from some weird place I’ve never heard of, that’s got a thin, you know, LinkedIn profile that probably just started yesterday with no picture. Like there’s no chance I’m going to answer that at all.

 

Jim Rozich:

There are a lot of … there was a period where I was getting a lot of fake LinkedIn profiles hitting me up for stuff, wanting to be connected to me. And I’d look at their profile and they had no information and nothing matched in the profile. And to this day, I haven’t figured out exactly what the scam was, but I knew there was a scam in there.

 

Todd Merrill:

Yeah, I think they were. Well, you know, there was these new tools come and go quickly. You know, with AI, would talk about that in a second. But, you know, AI lets you do a lot of damage in a hurry. So, I think it was go get, you know. So, like in the social, in the dating website world, somebody approached me at one point. They said, hey, we have a no, you know, like a new customer kind of problem. Like these people go and they capture a really attractive, like Russian news anchor picture and put that on a profile, and you go, oh, yeah, you know, that person looks really good, you know, incredible. And then they craft this brand new profile. So it’s kind of like a throwaway junk email for LinkedIn profile or social dating profile. How quickly can you craft these things and just spam the crap out of the world, you know? And then seem reasonable, I’ll connect, you know, but that I think people are kind of onto that now. And it’s good to be a little bit more discerning, particularly when you get five of those appear in one day. They’re obviously running the same tool on the same whatever.

 

Jim Rozich:

You know, you can see that now. You can see that in your emails and you can see that on the LinkedIn profiles. There are some very good AI tools that are for LinkedIn connecting that do just fine. There’s nothing wrong with them. For AI, which we might as well get into AI now.

 

Todd Merrill:

Yeah

 

Jim Rozich:

For AI, you know, I love it. I use it as much as possible. But it’s a tool, first of all. And you have to say, well, it can be used for good or it can be used for evil. So, it’s up to you how you use it. If you and I do this in some of my trainings is I will have ChatGPT or whatever, write an email. And the email is almost always feature-based for this product. It almost always says, I’d love to do a demo for you. You know, it’s what I quoted earlier. It’s my name is so and so, blah, blah, blah, blah, feature-based and blah, blah. And the reason is that at least so far, AI hasn’t figured out how to sell. It doesn’t understand human psychology, buyer’s psychology. So, it can only be feature-based. You know, I told somebody the other day, I’m like, ChatGPT doesn’t love to do demos. It loves electricity. That’s really all it loves.

 

Todd Merrill:

All right

 

Jim Rozich:

So, you got to think about that. So, what AI is great for in marketing is ideation.

 

Todd Merrill:

Yes, I agree.

 

Jim Rozich:

I’ve got I’ve got this customer. These are what a typical customer has pain points around, you know. What are some of the reasons that this customer would do this? What are some value-based observations on this type of customer? And then you can incorporate them into an email. What is plaguing this industry? So, AI is from a marketing and sales perspective. AI is great for ideation. Then you take that and you put it in a format that brings out that human touch, you know.

As we get more and more automated, the need for to personalization becomes more and more. You need to stand out more and more from your competition, but not just your competition, your competition for their mindset, their email box. If their email box is getting flooded with all the same emails, you don’t want to sound like that. And a lot of them are AI-driven and a lot of them are driven by people that don’t have any training on sales. So, if you don’t understand sales methodology and buyer psychology, then what you’re going to end up with is the same email. “I’m so and so. This is my company. We do this. Please, please, please, please. May I? Can we have a call? I want to solve it … I know I can solve your problem.” And I see it every day. And I don’t want to be like those people.

So, when you’re competing for mailbox share, for mind share, you have to stand out. You have to be a little bit different. There’s lots of these different emails. There’s the to the point email. How many times have you seen this? Hi, Todd. I’ll get right to the point. I sell lists. I got a list of 25,000 people that is going to make your life perfect. Sound good?

 

Todd Merrill:

Yeah

 

Jim Rozich:

Let’s have a call.

 

Todd Merrill:

Yeah, I got five or six of those in spam this morning.

 

Jim Rozich:

Sure

 

Todd Merrill:

It’s truly impressive. I was looking at spam in a fairly new startup account and you know, it was full of stuff like that. It’s like, wow, like this never even made it to my inbox because it was all cookie cutter same, and then spam filters got it really fast. You know, their AI got the other AI canceled each other out. It’s kind of fun.

 

Jim Rozich:

And that’s the other problem. If you sound like everyone else in the spam, filters are going to catch you as well.

 

Todd Merrill:

What AI tools are you looking at? I agree with the ideation, the creativity brain, is a great application for the generative LLM type AI that we’re seeing emerge. You mentioned ChatGPT as a favorite one, do you have any others that you like to use? Are there features?

 

Jim Rozich:

Yeah, I’m looking at Dripify, which is a tool for LinkedIn marketing.

 

Todd Merrill:

Okay

 

Jim Rozich:

Among other things.

 

Todd Merrill:

Okay

 

Jim Rozich:

So, I’m looking at that right now. I’m using a tool called Emelia, which is a LinkedIn scraper because I do a lot of my prospecting through sales navigator, which we can. That’s a whole nother topic, sales navigator.

 

Todd Merrill:

Good, bad or ugly or kind of complicated.

 

Jim Rozich:

A little bit of all three.

 

Todd Merrill:

Okay

 

Jim Rozich:

So, I do a lot of my work through sales navigator for clients and for myself. And it’s a little rough around the edges, but I’m happy with it. It scrapes and searches emails.

 

Todd Merrill:

Okay

 

Jim Rozich:

So, that’s the main thing is getting good data. And I still find LinkedIn has the best… I don’t buy lists. I don’t. You know, if you’re not going to do that kind of stuff, then LinkedIn is the best place to find the people that you are looking to reach out to.

 

Todd Merrill:

Okay. Talk about LinkedIn for a second. Ads, how do you, like, I think LinkedIn navigator, sales navigator, you kind of have to buy that at some point.

 

Jim Rozich:

Yeah

 

Todd Merrill:

And then you got to look at what’s going on.

 

Jim Rozich:

Call it the worst $80 I spend a month, but I have to do it.

 

Todd Merrill:

But you spend it.

 

Jim Rozich:

I spend it because I really need it. I’m not in the ads.

 

Todd Merrill:

Okay. Not at all?

 

Jim Rozich:

Yeah. No, not for me.

 

Todd Merrill:

So why? Like, you know. How do you think, like, is it ads later or ads never or ads are just a waste of money or?

 

Jim Rozich:

Ads later. Ads later.

 

Todd Merrill:

Okay

 

Jim Rozich:

I’m still trying to build my brand a bit, and so where I’m going is more kind of where you’ve gone and others have gone. I’m looking at channels like these podcasts. I’m looking at LinkedIn newsletter. So, as I move towards LinkedIn, I would say ads in the future. But I want to master the present right now. So doing more articles like I’m what we’re talking about. I’m email messaging. I’ve written a few blogs, but I haven’t put them on LinkedIn yet. So, I’m posting more on LinkedIn relevant info so that it gets in front of the people that I’m connected with and doing more connecting with the people that I’m interested in in working with.

 

Todd Merrill:

Okay. You mentioned LinkedIn is obviously in your stack and then HubSpot is obviously also in your stack. Do you have a mail component that you like to manage?

 

Jim Rozich:

I use a HubSpot mailing, you know, the marketing side of HubSpot, too.

 

Todd Merrill:

Okay

 

Jim Rozich:

So, you know HubSpot has … the beautiful thing about that is it’s integrated with the marketing tool. So, you have the sales side and the marketing side, and it has a support side. And again, this is something that a lot of founders don’t understand, is that a tool like HubSpot is certainly not the only one that can do this. But the more you can run your business with the less tools, the better your rev ups can be.

 

Todd Merrill:

Yeah. Amen, brother.

 

Jim Rozich:

So, if you have sales, marketing, and support all in one tool, then you’re generating data. That’s right in front of you and can be actionable. And that’s the goal. Generating data isn’t the goal. Actionable, being able to take actions on that data is the goal. Actions that increase revenue while limiting costs.

 

Todd Merrill:

So, talk about that feedback loop analytics. What does that look like when you measure, monitor how we do in on this email campaign? Is that a HubSpot thing or what are you specifically looking for? And then how do you adapt to that? And what does that kind of feedback loop look like?

 

Jim Rozich:

Yeah, so there’s a lot to look for. It seems so simple and yet there’s so much to look for. And that fits into the whole … it can play in so many different areas. But, you know, elementally from the simplest element, I guess, is how is this campaign performing? How do I measure this campaign? Do I measure it in terms of revenue? Well, that’s, you know, definitely you want to do that. But at first, you may be just looking at, you know, how is this? Am I getting new customers out of this? What am I getting out of this? What am I looking to get out of this? You have to define the parameters of your campaign. Why am I sending this message out? What’s it supposed to do? Once you understand that, then you can define how am I going to measure it? 

I’m looking at, you know, if you’re just sending cold emails out, one-to-one cold emails, then are people opening it? And if they’re opening it, how many of those opens am I getting appointments out of? If they’re not opening it, what’s the problem? Or if they’re opening it and I’m not getting appointments, then what’s the problem? So, my message is not resonating.

 

Todd Merrill:

So, I had a client that was suffering from, you know, looking at, you know, if you look at your funnel, you have to contact them. They say, yes, you get a meeting. Start talking and you qualify them, you know, blah, blah, blah, blah. And then eventually you get revenue. Well, I was arguing, hey, you know, nothing matters unless you’re getting revenue in a 10-million-dollar company, something like that. But the sales guy kept looking at this very early-stage. Now we’re getting meetings or we’re getting click throughs. And they never quite got past that, you know. So obviously click throughs are important, but how do you think about turning up this? You got to light up each one of these phases, right? In order, you know, how do you look at that? And then kind of do like, okay, we’re getting click throughs, and then now what? You know? Is it a different message or how do you coach people to kind of think about that process of lighting it up all the way through? Because eventually you got to sell something to somebody. Right? That’s a famous quote from one of my old board members. You know, it’s nothing matters. Motion and not progress.

 

Jim Rozich:

Where are they dropping out? You know, where are they dropping out? What are they doing? Are they going to the website? Is something going on on the website? What are they doing on the website? There’s website tracking tools. There’s heat maps, conversion rate optimization tools.

Again, you have to understand the sales process of your business in order to really understand your funnel. Once you do that, then you just have to find out where are they dropping out and then you start trying to figure out why they’re dropping out. I mean, at the end of days, you’re really right. I mean, somebody opens up an email. Great. So what? So, you get a click through. Okay, then what? You know, until somebody says, okay, you got a meeting. All right.

Well, if you’re getting a lot of meetings and then they’re dropping off, then there’s something going wrong in the meetings. If you’re doing a lot of demos and they’re not leading to sales, how many demos does it take you to get an actual sale? And is this right or is this wrong? If it takes you 10 demos to get a sale, maybe there’s something wrong here. What are we doing in our demos? So, then you have to tear the demo apart. Frequently, what you’ll see again with demo with, you know, what I call the people with founder’s disease, which I’ve worked for a couple is they will do a demo that takes 45 minutes to an hour for the whole demo.

 

Todd Merrill:

Oh, geez.

 

Jim Rozich:

And they talk the whole time and they show every feature of their tool, including, you know, the back office side of it, that the person you’re selling to doesn’t have anything to do with. They’re like, oh, I got to show you this. I got to show you this. And I actually had a funny story. I was working for a very small startup, very respected person in the industry. And we did this demo for this major salesperson. This consultant trainer, you know, real successful. And at the end of the demo, she said, I have no idea what I just saw.

 

Todd Merrill:

Oh, no.

 

Jim Rozich:

And he was like, he was so crestfallen.

 

Todd Merrill:

Yeah

 

Jim Rozich:

He’s been very successful in life. This was his third or fourth company.

 

Todd Merrill:

Right

 

Jim Rozich:

He was just like, ah, ah, because he’s going to show her this. Show her this. Show her this. And it just died.

 

Todd Merrill:

…you forgot the result.

 

Jim Rozich:

…it was all feature based.

 

 

Todd Merrill:

The first slide of why we’re doing this. Right.

 

Jim Rozich:

Why? I have no idea.

 

Todd Merrill:

Yeah

 

Jim Rozich:

So that’s what look at.

 

Todd Merrill:

You call it show up and throw up. Is that what you were saying?

 

Jim Rozich:

Yeah, that’s the show up and throw up demo. Yeah. So, everybody gets the same demo, right? Everybody gets the same one. Everybody’s the same when it’s not true, unless you’re really commoditizing your product.

 

Todd Merrill:

Yeah

 

Jim Rozich:

So, yeah, the show up and throw up demo.

 

Todd Merrill:

Well, I always feel like, you know, figure it out fast, fail forward, fail fast and pivot, right? Pivot hard early and often until you figure it out. So what, you know, you’ve seen probably some of these companies that take way too long and they’re in love with their product founder syndrome, I think, is what you call it. Happens all the time.

 

Jim Rozich:

Founder’s disease. Right.

 

Todd Merrill:

And then they’re not able to let go of this really, really awesome napkin idea. And, you know, but in the six, let’s talk about the happy path. Let’s talk about what does success look like or in the companies you’ve seen and helped. How fast does that happen? And then, you know, yeah, you get them to click. You got the messaging. They go to a website, sign up for a calendar, get a demo. And they go, I wouldn’t. That’s not what I thought it was. And then somebody kind of goes, you know, we keep hearing this objection, we’re probably going to fix that. And then you fix it, and then demos start going a little better. What’s that time typically look like? You know, in a happy path, like we’re figuring it out, very successful early-stage startup versus, you know, never quite get off the dime and don’t understand why they’re not, their bank account is empty, you know. They’re not able to draw funding because there’s no revenue.

 

Jim Rozich:

They’ve burned through all their money.

 

Todd Merrill:

Yeah

 

Jim Rozich:

Well, it’s hard to put or is it feel like a time frame? It’s because really what you should be knowing before you go into those demos and before you go into a demo with someone is you should know what they want to see on your product. So, it shouldn’t come out of the demo phase. It should be coming sooner than that. People should be telling you what’s resonating. That’s what a discovery call is. You’re there to discover. So, people are going to say if you do it right, and sometimes it takes a couple of calls before you get to your demo. But now the way things are compressed nowadays in time, you’re trying to do your discovery, your demo, and then, send a proposal. You can talk all day about if that’s the right way or not, but that’s kind of the way it is now, yeah.

 

Todd Merrill:

Sounds good. Yeah.

 

Jim Rozich:

But let’s say during the discovery call, if you’ve conducted it properly and you’re not doing all the talking, remember, the human nature is I’m going to talk all about my product for 20 of the 30 minutes when it really should be the other way. The client should be talking about their business for 20 of those 30 minutes or something along those lines. So hopefully during your discovery calls, during your early meetings with clients, you’re figuring out what’s important to them and what they need to see in the demo to sell the product. And then you focus on that in the demo. You don’t have to show everything. Ideally, if you get it right, a demo is really just to show that it does what it’s supposed to do.

 

Todd Merrill:

Yeah

 

Jim Rozich:

See, it’s easy to use. I told you that it will do this, this and this. You have this problem. You know, this, this and this is what you want to solve. Here’s how we solve this, this and this. It’s easy. Okay. That’s an ideal, perfect world.

 

Todd Merrill:

Okay. I was just thinking, you know, where you’re talking, which is always dangerous. So that that early discovery, you know, there’s difference between a discovery call and a sales call in a demo or in a closing call, even. Right? So, you have to do them in order. You have to discover, especially early, how do you talk about, how you distill your learning? Very fast. People talk about learning organizations. Every discovery call, you learn a little bit more about your customer in particular, but the market in general. And then you have to put that somewhere, like in a CRM or something. And I was thinking about all these cool little like, you know, I got this plot. You know, we all have these AI read, Otter, these are things that kind of pop into your Zoom and record and analyze and all these new AI tools that are out there. You know, we have such a great power to distill these insights and put them somewhere. It’s a whole nother data management problem. Right? How do we think about that? How do you get organized around that? What’s the right tool? Is the CRM the right place? Is it something else? Or how are you reacting to this new kind of, this flood of information?

 

Jim Rozich:

Well, I think that you always want to try to spend as much time in the CRM as possible, that that should be your base product. You are paying for it. And in all likelihood, you’re getting all kinds of tools within the CRM that many of us don’t even use. Going back to HubSpot, it has a e-signing platform, so you can put your proposals together through it, send it out and invoice through it. So why is that useful? Well, the obvious solution has to do with not having to buy other tools. But the less obvious solution is now you’re tracking. It becomes part of the funnel.

Now you are once again having some predictability, having some data right in front of you that you can report on to figure out where things are going wrong in your process and monitor. We have this person. We have this amount of people in this stage. So now you have revenue predictability, things like that.

So, there’s tools within the CRM that, again, many people don’t take advantage of and don’t use. So going back to your question, data management is really part of that whole revenue ops philosophy. It’s part of taking a look at what data we have and how can we best track it. Can we do it in the CRM? Can we have a checklist? Yes, you can. You can have all kinds of checklists in the CRM that say, okay, how does client fit in? Does client have a need? Does client have this? You know, who is this client? Bang, bang, bang, bang, bang.

So, there are ways to do that within your CRM. And again, this is nothing new. People have been qualifying their clients for thousands of years. You can probably go back 2000 years ago and find clay tablets of Sumerian writing about various clients and what they like and how they like their pickles and fish sauce and things like that. It’s nothing new. It’s just a new way of organizing it. That’s all.

 

Todd Merrill:

Got it. So, it sounds like you hang everything off the CRM where possible and then you can go back to that retrospective strategic review.

 

Jim Rozich:

Try to… because of the back end, those reporting capabilities. That’s where it’s telling you. That’s where the magic is.

 

Todd Merrill:

Show me all the deals that close Q4. Okay, what do they all have in common? What do we say? What were the objections that we overcame? Okay, let’s do more.

 

Jim Rozich:

What can I look for? What’s going on in my CRM? So, what can I look forward to 6 months from now?

 

Todd Merrill:

Okay, okay.

 

Jim Rozich:

And if I’m not where I want to be in 6 months, what do I have to do to get there? How do I scale? And what’s it going to cost me?

 

Todd Merrill:

Got it.

 

Jim Rozich:

Do I need to hire somebody new? If I hire somebody new, what is my return? Is it 3X? Is it 10X? What return do I need to have to make this higher, to pay somebody $100 000 a year or whatever its salary is nowadays to do this.

 

Todd Merrill:

Do you like the SDR model used to be? You know, you make a bazillion calls and you send out a bazillion emails and then you have a ratio and then you hire a bunch of very, very young, fresh out sales folks that are very positive and go getters. Is that still the play? Is it or we have to be a little smarter than that?

 

Jim Rozich:

I do not like the SDR model. I may be going against the grain here.

 

Todd Merrill:

No, no, I think that’s secular. That’s the winds of change are here. Right? For a minute, that was the hot thing.

 

Jim Rozich:

Yeah. I’ve used SDR models before. Actually, it’s kind of funny. This one company that I was working for engaged a deal with a … I don’t even know what you would call this type of company, an SDR company, and this company actually was located in a women’s prison.

 

Todd Merrill:

Oh!

 

Jim Rozich:

So, I went to a women’s prison to train people.

 

Todd Merrill:

No kidding.

 

Jim Rozich:

So, I tell people, yeah, I’ve been to prison. Sometimes that backfires.

 

Todd Merrill:

Yeah, yeah.

 

Jim Rozich:

So, we had a group of SDRs who are female inmates at a prison in Arizona that made outbound calls for us and set appointments. But I didn’t find the results that compelling, and I still believe that this is part of the personalization. This is part of the human touch. And this is part of knowing your customer. Like, I’m looking at these customers. I’m doing research into them so that when I reach out to them, I know something about them. And I believe that I get higher value appointments. It’s not about the quantity of appointments. It’s about the quality of the people you’re reaching. 

 

Todd Merrill:

Yeah. You’d rather have three phone calls a day if they were the exact right phone calls.

 

Jim Rozich:

…oh, yeah.

 

Todd Merrill:

…than you know a hundred or 50.

 

Jim Rozich:

Yeah. That’s a different mindset because everything to do with AI Is about quantity. We can spit out even more of this stuff.

 

Todd Merrill:

Well, and that’s on the generative side. I do think there’s something to be said for the other part of this, where I love the part of LLM technology where you say, here are a thousand papers, go read them all for me and find the ones that are most likely to talk about A, B, and C. And then now it can go through that stack and find me the five papers I really need to write or read. And then, you know, I’m not going to trust AI to summarize it accurately if it’s a highly technical thing. But yeah, you can cut my work down. I’m not going to read a thousand papers. You know, I can do things like that.

 

Jim Rozich:

Right. I think that’s good work to be. That’s working more efficiently. That’s working smarter, not harder.

 

Todd Merrill:

Right

 

Jim Rozich:

So that’s good. And let’s face it. With AI, we’re just scratching the surface.

 

Todd Merrill:

Oh, yeah. For sure.

 

Jim Rozich:

It’s going to be doing stuff in in several years that is going to be truly amazing. The stuff it’s doing right now is yeah. I mean, it’s going to… yeah. So, we’re just using it to write emails. That’s, come on

 

Todd Merrill:

Yeah. That’s kindergarten. You got anything you’re looking at for the future in terms of AI? I mean, what’s the next kind of big thing you’re looking at in the market or even in RevOps in general? What are you excited about or what would you buy if it was ready tomorrow that’s not quite there yet?

 

Jim Rozich:

What would I buy if it’s ready tomorrow? Anything that really helps me understand what my potential customers need that will help them buy. Anything that helps me give buying insights, I’m interested in. Anything that helps me better understand buyer psychology, I’m interested in.

 

Todd Merrill:

So, for all the entrepreneurs out there in the world that want AI project, there you go. There’s a good one. Human psychology, understand human psychology of buying.

 

Jim Rozich:

Yeah because, again, AI doesn’t understand that.

 

Todd Merrill:

Yeah. Well, yeah. But can it help intelligent experience sales force focus on certain things that are more likely than less likely? Yeah. Yeah. Maybe that’s well, maybe we can do that.

 

Jim Rozich:

You know, where can I provide value? It’s really always boils down to value. This person is willing to give me some of their time, there’s a cost to that. So, they have to perceive they’re getting something back in value. So, what brings them value that would want them to have a conversation with me?

 

Todd Merrill:

Very cool. Well, it’s been great having you here in the Sky Lounge for an hour. You got a great some travel stories that you’d like to share with us.

 

Jim Rozich:

Yeah. So, my wife and I went to Rome earlier this year.

 

Todd Merrill:

Okay

 

Jim Rozich:

And I did a plethora of research before going there. I read travel books, YouTube videos, documentaries on the Baroque period of art because, you know, a lot of what was going on in Rome in the 1500s, the Baroque period from a religious sense. That was when the Protestant Reformation was happening. So, there was huge upheaval and art that just exploded then. And so I did a ton of research on that. I was super excited to get there. And it was one of the first times, one of the few times where I was not disappointed, where I had super high expectations and went in there and was just absolutely flabbergasted by what I saw and what I experienced. And it was just one of those trips. And anybody that knows that travels or especially travels internationally, something always goes wrong. And yet nothing went wrong. I’m like, oh, every day was great. The weather was perfect. We went in late January.

 

Todd Merrill:

Okay

 

Jim Rozich:

Which nobody goes in late January. It is literally half price to go there.

 

Todd Merrill:

No kidding.

 

Jim Rozich:

And there were hardly any tourists. You have to get the big museums. You have to always have tickets in advance, but there were museums we just walked into that you would not be able to do that in the summer. But it was truly amazing. I’m trying to figure out how to get back there as soon as possible. But yeah, that was amazing.

 

Todd Merrill:

Well, very cool. Well, following up from this, how can people follow up with you on the Internet if they want to talk to you after this?

 

Jim Rozich:

Wheelsupsales.com is my website. Best place to go fill out a form. And let’s have a conversation. Let’s see what kind of value I can bring to your organization.

 

Todd Merrill:

Very cool. Well, Jim, thanks for being here in the Sky Lounge. And bye for now.

 

Jim Rozich:

Thanks. Really enjoyed it.

What is the Sky Lounge?

Tales from the Sky Lounge is a podcast where we take you on a journey through the world of business, consulting, and venture investing. In each episode, we gather in our virtual sky lounge, high above the hustle and bustle of the everyday world, to hear stories from the people who are shaping the future of these industries. From entrepreneurs who are disrupting the status quo, consultants who are helping companies solve their biggest challenges, and investors who are making bets on the next big thing.

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ABOUT OUR HOST

Todd Merrill, Interim and Fractional CTO, CISO

Todd Merrill is an experienced software executive who typically assists clients as a fractional or interim CTO and CiSO as a partner at TechCXO.

He has served in a series of companies as a C-Level executive focused on leveraging the Cloud to bring SaaS offerings to market. As an entrepreneur, turn-around expert, technology and product leader, and mentor, Todd has held full corporate P&L and product development responsibilities and directed diverse international teams of Engineering Managers, Mobile Architects, Developers, Dev Ops, QA, and Customer Success professionals.

Connect with and learn more about Todd here:

email: Todd@SilverbackCTO.com
phone: +1 678-521-5305
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