You Can’t Automate What You Don’t Understand: The Human Intelligence Behind Financial Fluency

Full Episode Transcript

This is the full recorded conversation from The Human Protocol Podcast, published by The Human Protocol Group. © 2026 The Human Protocol Group. Please link to and attribute the original episode when referencing this conversation.

THE HUMAN PROTOCOL PODCAST (00:03.246)
Hello, welcome to the Human Protocol, the podcast about staying human while building the future with AI. I'm your host, Mykel Salomon. We are at a real turning point where companies write algorithms, governments write laws, but who's gonna write our human story? This is what this podcast and this space is and will be about. Every week, we explore how technology, leadership, and purpose intersect.

and how our values endure in a world being rewritten by code. Today I'm very excited because I'm joined by Jay Nathan. Jay is a tech executive and entrepreneur passionate about growing businesses, building high-performing teams, and delivering value for customers. Over the past 20 years, he has built and led post sales customer success, services, support, and account management teams.

across a range of companies from bootstrapped startups to publicly traded enterprises, one million to 600 million in annual revenue. So his expertise lies in driving customer retention, expansion, and channeled growth. Jay, welcome to the Human Protocol.

Jay Nathan (01:21.942)
Thanks Michael, it's great to be here with you.

THE HUMAN PROTOCOL PODCAST (01:24.498)
I appreciate you taking the time from your very busy schedule to have this very important conversation with us today. And to kick things off and kind of introduce you a little bit for our audience, I want to start with a question that I ask every single guest that comes to the show, which is when we remove everything, LinkedIn knows about you. Who is Jay at his core?

Jay Nathan (01:47.256)
That's a great question. Well, thanks for having me. Always fun to chat about this stuff and I'm eager to hear what you've learned doing this podcast as well. But yeah, so what am I if I don't have my LinkedIn profile to lean on? I'm a father of three, been married for 22 years. So I consider myself a family man, follower of God. And I, you know,

I just, I, um, every day and trying to just be, uh, I don't know a better, better, better human being, uh, be more supportive of both my family and my colleagues. And, um, just trying to leave a positive impact on the world. Um, my hobbies, let's see hobby I've got. I've played the guitar for about 30, 32, 33 years. I always tell people I never got any better after the first year.

that I learned how to play, but I've been hacking away at that for a long time. So it's something I really, it is, yeah, something I really enjoy, mostly rhythm guitar. So you won't catch me playing a lot of solos and screaming guitar licks, but mostly acoustic and rhythm kind of stuff. So yeah, so that's a little bit about me.

THE HUMAN PROTOCOL PODCAST (02:46.126)
You

Feel the passion, right?

THE HUMAN PROTOCOL PODCAST (03:04.736)
Awesome. Thanks for sharing that. It's pretty cool. Every time you have kind of a passion like, you know, playing the guitar or something like that, it's kind of cool to hear that from people. And when we first discuss about what are the topics or the angles that we could discuss today, I know that you have a few topics, Yeh, that you're very passionate about. But before we get there, right, what made you to be...

and passionate about the world of customer success and services overall. How did you get started there and what have you seen transitioning from when you started to today?

Jay Nathan (03:37.911)
Yeah.

Jay Nathan (03:45.232)
Yeah, great, great question. I guess, you know, I've connected myself with this thing called customer success, but I'll be very clear, I hope about what I actually believe related to it. But I would say serving customers, I got that itch from my parents when I was very young.

And through my formative years, my teenage years, even my college years, my parents were entrepreneurs. They ran businesses of their own. And I watched my mom in the business that we were in really focus on high quality delivery for customers, like high value for what it is they paid. They probably didn't pay her enough for the products that she sold, that she handcrafted, put so much time and energy into making the best they could possibly be. But it was little things that mattered to her.

THE HUMAN PROTOCOL PODCAST (04:27.0)
Hmm.

THE HUMAN PROTOCOL PODCAST (04:32.013)
Right.

Jay Nathan (04:41.304)
Uh, in that business and over the years that business grew and grew and grew, um, became more and more well known. And it was because of those little things in the high quality. And so I guess I've always carried that forward with me when I came out of college, I had a business degree, but I had also taught myself how to code. And I, my first job was an in like a straight engineering job in an internal IT shop. came out of school in 2001, the economy sort of sucked.

at that point in time, because the dot com bubble had just burst. There weren't a lot of jobs out there to have, but I was passionate about software development and I wanted to be a hands-on developer. But I was also the guy that would also go do the training with all the users, right? We build software for teams. I worked for a company called Duke Energy here in the Southeast and we deployed software. We wrote, hand wrote software and deployed it to nuclear power plants.

It was not all nuclear power operations. was like learning management platforms and all kinds of other business systems around the nuclear organization, but high process, high dependency on quality. And, but I was always the guy who wanted to build stuff and then go see how the users used it, get their feedback, teach them how to use it. And so I've always wanted to be in front of customers. From there, I sort of moved into the software world in consulting.

THE HUMAN PROTOCOL PODCAST (05:38.505)
wow.

Jay Nathan (06:07.672)
where I spent even more time with customers, even more time on sales and helping customer like connect the value of the technology that I was representing to the customer from a technology, like a deep technical standpoint. And I ran professional services teams. I moved into product management for a period of time. Then I became an executive at a smaller software company in 2010, 2011, and actually 2013 is when it was. And I

I got to sort of be part of the executive team and my focus then changed from departmental product or services or any of the other areas that are represented in a software company. And it became sort of this P and L focus, right? How does all the business fit together? had a CFO who mentored me there. So I'll, I'm talking a lot here, but I'll sum it up to say this. I've tried to make my entire career.

around blurring the lines between departments and making our companies work, the companies that I've worked for work for the customer because the department structure is just the way we keep ourselves organized. does nothing, nothing for the customer, nothing. It actually makes the customer's life worse in some companies because they have the wrong culture. And so,

You know, I sort of latched on to customer success as an extension of that mindset. There's a whole bunch of reasons that I could tell you, maybe we'll get into it, that I think customer success is fundamentally broken and that that is not the answer. The department of customer success isn't the answer, but conceptually, that's why I got into customer success because I believe in blurring the lines and driving value for the customer and making that work despite.

THE HUMAN PROTOCOL PODCAST (07:42.734)
Mm-hmm.

THE HUMAN PROTOCOL PODCAST (07:47.459)
Right.

Jay Nathan (07:57.43)
the structure of our organization. So it's probably more than you were bargaining for, but there you go.

THE HUMAN PROTOCOL PODCAST (08:01.57)
And then, that's awesome. Because it's a, what you're telling me, it's kind of music to my ears because I'm very customer focused type of person and professional. And I think everything we do, right, in across our organizations, if you have the customer first type of mentality and you bring the customer, as you were telling me, I was just paying attention from the very beginning, every single task and role you were in front of the customer. And I think.

Fundamentally, what's broken today is what we call customer success or customer obsessed is having the customer at the end of the line instead of including the customer as part of the customer journey as it should be. So I think that that type of experience, I see that it's also missing today because it's not everybody that is putting the customer in front of our processes, building with the customer and for our customer.

So, so great to hear that from you because that's that kind of the type of, you know, mentality and business that that we need to build. Right. At the end of the day.

Jay Nathan (09:02.07)
Yeah. And it rewards, it rewards us at the end of the day, right? If you, it's a self fulfilling prophecy. think that the challenge that we've had, particularly in tech is that over the past 15, 17 years, we've had all this money flowing in. talked a little bit about it before we started recording all this money flowing into our software companies is it's sort of been, a false sense of security that we are delivering for our customers. Right. And,

THE HUMAN PROTOCOL PODCAST (09:05.109)
Exactly.

Jay Nathan (09:31.848)
And it's a short term mindset, right? When you just have to get to the next fundraise, you think short term. You think shorter term, right? And your investors, whether you like it or not, ultimately end up thinking short term for you because they have a return to make. And so I think if you look at the landscape, the companies who grow to be the multi-billion dollar companies, and I'm not even talking about software companies anymore.

THE HUMAN PROTOCOL PODCAST (09:36.576)
Mm-hmm. Yeah. Even shorter, right?

Jay Nathan (09:57.57)
But the companies that grow to be the multi-billion dollar software companies go look at the greatest founders in the world. They've relentlessly focused for long periods of time, decades of time on putting the customer first and they build this moat around themselves that is impenetrable. so anyway, yeah, just to double down on what you said there, I think it's a long-term focus kind of mindset that helps there.

THE HUMAN PROTOCOL PODCAST (10:25.39)
It really is and it needs to be kind of, you know, a partnership with all departments in our organization. So every single one, including backends, right? Every single one should be customer first, customer obsessed. What are we building our product and our services for? It's at the end of the day for our customers. Kind of a mentality and a mindset shift. Absolutely. And how do you see, Jay, as you were mentioning every single aspect of your

Jay Nathan (10:35.554)
Yep.

THE HUMAN PROTOCOL PODCAST (10:55.306)
of your career and you were talking and what are that type of kind of financial illiteracy that you think it's really needed for business leaders today that we don't talk a lot, right?

Jay Nathan (11:09.622)
Yeah, yeah. And I would say that customer success has this problem particularly badly is that there are not enough, there's not enough business acumen in our, our software companies. would say as it maybe as a result of the short term ism that I mentioned earlier, we've done a pretty mediocre job of educating our, our teams, especially our leadership teams on what it actually means to be financial.

financially literate from a corporate standpoint. Like, do you know what a profit and loss statement is? Do you know where the expenses for your team fall? Because if they fall in one bucket or another, it changes the way that investors look at the business. changes the way that you should think about how you serve the business as well. for years, I've heard customer success people, and by the way, others as well.

THE HUMAN PROTOCOL PODCAST (11:40.642)
Mm-hmm.

THE HUMAN PROTOCOL PODCAST (12:00.525)
Mm-hmm.

Jay Nathan (12:08.632)
product people are notorious about this. They'll make comments about, well, if sales gets all the money, right? Or marketing spends all the money and we just get what's left over. Well, there are some really good reasons for that because, you know, on the flip side of all of that we've talked about on the customer side of things, we are still running businesses. The only way that you can serve customers for the long run is to create a healthy, profitable business in the long run, right? If you want to stay independent, stay true to your vision.

you have to be able to deliver on the business side of things as well. I've seen a lot of folks make comments like, the sales team gets all the money without really understanding what they're even saying, right? Because actually the money that comes, that goes to sales comes out of a different bucket than the money that goes to most customer success support services.

THE HUMAN PROTOCOL PODCAST (12:59.586)
Mm-hmm.

THE HUMAN PROTOCOL PODCAST (13:03.384)
Right.

Jay Nathan (13:04.184)
teams and there are good reasons for that. anyway, I just got real passionate about this a couple of years ago. Actually about this time, two years ago, I started getting the edge and I decided to write and record a course on financial literacy for SAS leaders. And so we've had CMOs, chief product officers, chief revenue officers, tons of customer success leaders and chief customer officers take this course. We call it cover your SAS. Just being funny.

THE HUMAN PROTOCOL PODCAST (13:32.334)
Cover your task.

Jay Nathan (13:33.612)
Cover your sass. Yeah. But, but created this course just, just a, because I wanted to make sure my knowledge of it was as deep as I thought. And by the way, I learned a ton making that course. and then B we wanted to, you know, try our hand at creating a product that, people could, learn from and further their careers. Because when you gain financial literacy, you gain a new facet, your ability to contribute and make an impact.

is increased. And so, yeah, yeah.

THE HUMAN PROTOCOL PODCAST (14:03.966)
It's different, right? How you approach even your operations and your business, right? Because you are looking at other opportunities and other things, not only just being proactive for the most part.

Jay Nathan (14:16.312)
That's right. That's right. We're always in this balance of being proactive, taking care of customers, and then also making sure that we do that in a profitable way. The purpose of a SaaS company is to create profitable revenue stream, a recurring profitable revenue stream for the business. to do that, have to have, it's just a very cyclical thing. One feeds the other.

THE HUMAN PROTOCOL PODCAST (14:21.144)
Alright.

THE HUMAN PROTOCOL PODCAST (14:35.47)
But yeah.

THE HUMAN PROTOCOL PODCAST (14:41.91)
And it sounds simple, but as you were saying through, you know, through history, a lot of business leaders in customer support or customer success, customer facing operations, they have been leaving the financial side of things to sales, for example, or others taking care of commercials. But I think that we need that type of knowledge and that type of mindset brought into our operations. Because as you were saying, how are we going to make sure that we're running

a successful operation when you don't even know what it costs you to run your operation. And if we are making sense commercially of the services that we are implementing and delivering to our customers, right? It cannot be sustainable unless we are in control of our finances.

Jay Nathan (15:17.676)
Yeah.

Jay Nathan (15:31.49)
That's right. And let me tell you, you know, one of the little understood phenomena outside of sales is how hard it actually is to sell a customer, sell something to a customer, especially today with all the security requirements and, and, you know, data protection and HIPAA compliance and all the different, you know, legal and data protection.

THE HUMAN PROTOCOL PODCAST (15:53.506)
Mm.

Jay Nathan (16:01.108)
that our clients expect from our companies, selling a dollar of ARR is no joke, Michael, right? And people don't appreciate it. If you've never done it, you will never appreciate it. And by the way, I'll say the same thing on the converse, right? Is that people who have never tried to protect a dollar of revenue often don't appreciate it either, right? And so that's the common concern and gripe we hear from the customer success side of things. But let me tell you, selling is hard.

THE HUMAN PROTOCOL PODCAST (16:09.186)
Yeah.

No.

THE HUMAN PROTOCOL PODCAST (16:22.432)
You what

Jay Nathan (16:30.646)
Because I've spent the majority of my past 10 or 15 years just focused on that. Like I know firsthand, selling is not easy to do.

THE HUMAN PROTOCOL PODCAST (16:37.856)
And you've seen it getting worse and worse and worse. It's getting more complicated for all these factors, not even taking into consideration the competition that we're facing today in many areas, right?

Jay Nathan (16:40.908)
Yeah. Yep.

Jay Nathan (16:48.268)
Yep, the channels are getting more crowded. The cost of getting somebody's attention has gone up, right? And so, but this all, guess to bring it back to your podcast, this all speaks to something that I'm seeing, which is the companies that are gonna succeed will maintain a human connection to their target audience, their target market.

THE HUMAN PROTOCOL PODCAST (16:54.606)
Mm-hmm.

Jay Nathan (17:13.844)
more so than they'll try to digitize and processize everything, right? And guess what? Some of these companies may be smaller because the way the world works in this huge ecosystem and technology driven ecosystem we're in is that you win in niches. You win in like little groups of customers at a time, little cohorts. But at the same time, it doesn't cost as much to start a company, especially in the tech space, where you can build a product

THE HUMAN PROTOCOL PODCAST (17:17.197)
Right.

THE HUMAN PROTOCOL PODCAST (17:30.424)
Mm-hmm.

Jay Nathan (17:42.614)
You know, utilizing open source and AI and all these platforms. Yeah. Yeah.

THE HUMAN PROTOCOL PODCAST (17:44.888)
Right? And AI, especially with AI, right? And I think that's why we're also seeing it as a kind of more leaner approach to building product and starting companies, because AI will help with a lot of back-end and operational tasks that in the past you needed maybe to hire people for. But at the same time, you know, it's what is going to make your company and your products still unique. That's where the human factor of things will still need to come into place.

Jay Nathan (18:04.504)
That's right.

Jay Nathan (18:14.53)
That's right.

THE HUMAN PROTOCOL PODCAST (18:14.926)
which should be extremely important as part of all these conversations.

Jay Nathan (18:19.372)
Well, and you know what's also interesting about what you just said. The human factor is important and you mentioned earlier the customer journey. I a lot of people, I hope I'm not frozen here, but a lot of people.

THE HUMAN PROTOCOL PODCAST (18:51.17)
Yeah, you froze right now.

Jay Nathan (18:54.936)
Come on.

Jay Nathan (19:04.92)
Michael, I don't know if you can hear me or not, but I'm just gonna wait until I can see you moving again.

THE HUMAN PROTOCOL PODCAST (20:05.507)
us.

THE HUMAN PROTOCOL PODCAST (21:53.077)
I lost you.