Sales, Marketing, and AI: How to Survive, Scale, and Avoid Stagnation
Joining us today in the Sky Lounge is Alan Gold, a marketing and sales strategist with decades of experience in M&A, startups, and growth strategy. Alan has been on both sides of the table—helping companies scale, navigating acquisitions, and leading turnarounds. From being part of the launch team for Wi-Fi technology to working on speech recognition and AI-powered business tools, he’s seen how markets evolve and what it really takes to stay ahead.
We dive into:
- M&A trends—why some companies are stuck while others are thriving
- The hard truth about growth and why some businesses hit a ceiling
- The real role of strategy in marketing (hint: it’s not just about SEO and PPC)
- How AI is reshaping sales and marketing, and what’s next for the industry
- Why most companies miss the mark when hiring sales leadership
Plus, Alan shares hilarious and wild travel stories, including a baboon with an attitude and getting detained in Colombia.
If you’re in startups, consulting, M&A, or just trying to grow a business, this one’s for you.
ABOUT OUR GUEST
Alan’s a veteran of the B2B marketing world, having been an executive in startups, international public companies, high growth technology and services companies, leading marketing and sometimes both marketing and sales efforts. Over my career I have launched new technologies that are integral to our daily lives, repositioned companies to take advantage of new markets, and been involved in M&A activities on both sides of the process. I’ve worked in many different industries, including software, supply chain, medical and pharma and healthcare applications and services, as well as telecom and AI-driven planning software. My greatest strengths are the ability to see problems and devise solutions, to explain simply complex issues, and develop high performing teams.
Socials
Instagram: https://www.instagram.com/alane._gold/
LinkedIn: www.linkedin.com/in/alanegold
Contact
alan.gold@techcxo.com
978-886-1910
I think what has happened in many ways is the pendulum has swung to something that I call "looking at the wrong side of the decimal point." And, you know, there's an attempt to monetize down to an individual event level, an individual email, an individual click to find out how much,…value was generated from that activity. In reality, nobody buys from one thing.
Alan Gold
ALAN'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 and 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 a word out. Today’s guest in the Sky Lounge, Alan Gold. Hi, Alan!
Alan Gold:
Hello, Todd. Great to be here.
Todd Merrill:
It’s great to see you again. Hey, Alan, who are you and what are you working on?
Alan Gold:
Well, most of it I can’t talk about or I’d have to shoot you. But the part that I can talk about is having spent the last 30-plus years in marketing and sales through technology primarily, but other companies as well. I’ve been in all sorts of technologies that are sort of things that we do every day. I was on a launch team for Wi-Fi technology. If you look at the back of your driver’s license, you’ll see a really bad-looking barcode. I worked with that. It’s called PDF417. I’ve been involved in speech recognition from its earliest days all the way up to different kinds of AI-informed management tools. It’s been an interesting journey.
I’ve been in startup companies. I’ve been on both sides of mergers and acquisitions. I have taken companies private, have taken companies public. About eight years ago, I decided to step out of the M&A world and become a consultant. I did that on my own with a number of different long-term clients, everything from pharma to social services, and joined our company, TechCXO, a year and a half ago for a number of really positive reasons, to have access to lots of experts, where I may need some to bring in on an account, and also to have a peer group to share ideas and get ideas from. That’s where I am now.
Todd Merrill:
Yeah. That’s awesome. Well, you said M&A and you piqued my interest there. I’m about to go to a conference next week, M&A South, so everybody’s going to be talking about M&A. At the end of the year, you talk to lots of funds and you get the updates from all these companies and everything. Boy, it sure feels like we’re at an inflection point in the market. I’m not sure if that’s good or bad with mergers and acquisitions and exits and all that kind of stuff. I got a lot of information from some of these folks that are in the venture world. Hey, we sure do need some healthy exits to free up some of this cash to get the engine going again. Everything is cyclical. What are you seeing out there in the world as far as M&A and exits and that kind of thing in general?
Alan Gold:
Well, it’s a bit of a mix. As you implied, frankly, it’s an uncertain time. Whenever a new administration comes in of any sort, it is always a time for a little bit of reflection and waiting for the market to settle. I noticed recently the market, after having been on an upramp, has taken a step back. It’s unclear what the cost of money is going to be in this next year. It’s also unclear what the appetite is for acquisition of goods and services, whether that’s in the B2B realm or in the consumer realm. So, I think where there are going to be successful transitions or exits, it’s going to have to be around things that are particularly compelling, that feel not necessarily a basic need, but one that does basic things better or creates a new category of functionality that gives either a company or individuals an opportunity to leapfrog the way they’re doing things now. So, I think uncertainty is the phrase I would use, though there are certainly opportunities out there.
Todd Merrill:
Yeah. As Warren Buffett said, you know, when a recession happens, the tide goes out and you get to see you swimming naked.
Alan Gold:
Exactly.
Todd Merrill:
There’s always good opportunities for people who run solid little businesses or solid big businesses. If you do a good job, you meet somebody’s needs and desires and are in tune with it. It seems like you’re going to be fine and you’re going to pick up some opportunities that other people may not be able to take advantage of in this market.
Alan Gold:
Yeah
Todd Merrill:
Generally, Sunshine, is it the train engine coming down the tunnel or is it the sunshine at the other end?
Alan Gold:
Well, that’s always the question, right? You know, how lucky do you feel in this?
Todd Merrill:
Right
Alan Gold:
I think there genuinely are opportunities for at least tuck-ins. There’s lots of opportunity to do that, to round out a portfolio. I think both businesses and consumers are tired of going to six different places for six different things. There’s the usual argument around a point solution or all in one. If you’re talking about technology or functionality. And if you’re on the services side of things, as competition gets more difficult, as it becomes harder to differentiate yourself, I’m in marketing and sales, so I always think about differentiation, so if you are in a really crowded field, you want to be looking for things either through acquisition or from internal development, things that are going to separate you, and then you have to have a message that’s going to be really resonant with that marketplace. That ties to M&A because the more you can differentiate yourself, the more likely you are to get the attention for a suitable exit or an acquisition event.
Todd Merrill:
You said, tuck-in. That’s an interesting word. Maybe describe what that is and then maybe an example of when you did one of those.
Alan Gold:
Well, a tuck-in, at least in my vocabulary, is a company that has any number of capabilities, but there are gaps in the functionality. If you were, I don’t know, let’s say you were a shipping software company, but you had a gap for small package shipments, and you’ve got standalones like stamps.com and two or three others. Pitney Bowes has tools, but you as a company would like to have all a business, but if you’re missing that gap in the small parcel and the letter package shipping, you might find a company that does only that and buys that. They’re usually short-dollar acquisitions, a handful of millions of dollars to bring them in, but for you, it’s a multiplier effect because now you can say you’re an all-singing, all-dancing provider. So, a tuck-in is finding a capability or functionality or a market segment for that matter that you don’t have access to that isn’t a huge acquisition cost or a disruptive merger, but rather gives you a set of capabilities that you can fold into the organization without paying.
Todd Merrill:
Yeah. Right now, it occurred to me that in this particular market dynamics season, there are a lot of small underfunded companies because a lot of funds are just handing out lifelines rather than gross capital. At some point, if you have a nice little company that has a point solution, but you haven’t been able to expand as rapidly as you want just due to capital access, that would make a lot of sense to join up with someone who’s in the market, has market share, and to fill in a portfolio need that’s complementary. It’s not necessarily a fire sale, but just joint forces, right?
Alan Gold:
Right
Todd Merrill:
Be a part of something that’s a little bigger.
Alan Gold:
Yeah. I mean, look, it’s hard to grow. It’s really hard to grow. And if you are capital limited and you don’t have a clear path to that growth because you’re either in a crowded market or your solution just isn’t that big, you know, it probably makes much more sense to find someone who wants to pick up that capability rather than building it themselves. It’s the classic builder buy solution discussion to have, or you find a way to maintain that business at that level, which is really hard to do because inevitably something else comes along or someone has a more comprehensive suite or a larger company comes in and there’s an opportunity to de-risk working with a small company. Either way, you’re vulnerable, so you might as well be proactive and go find someone to partner with.
Todd Merrill:
Yeah. Yeah. Keep your technology going.
Alan Gold:
Exactly.
Todd Merrill:
Before you become the fire sale you have to get out rather than a nice little exit, right?
Alan Gold:
Exactly.
Todd Merrill:
A couple of base hits are better than a fire sale for sure. We’ll talk about the other side of that. I think the other opportunity right now, PE used to do this, maybe not necessarily technology, but other types of companies where you have a roll-up scenario or someone thoughtfully thinks about, okay, you know, we’ve all heard about PE going, and gobbling up physicians or HVAC companies or plumbers, that kind of thing. I think in software, we’ve all played that game as well where you think, okay, we could spend a bazillion dollars and we could develop this technology ourselves or we could go to the market, pick up three or four people, companies that are doing exactly what we want, and then maybe have a little bit of a bake-off, stay close to them for a half year, a year, and then carefully cherry-pick the best ones and put together something that’s really interesting, like a jigsaw puzzle, and then grow from a $20 million company to a $50 or $100 million company, and then produce really healthy exits in that way. Have you ever done one of those, especially in technology?
Alan Gold:
Yeah, I’ve been part of a lot of roll-ups. And some of them have been three and four times, as the case may be, which is kind of head-spinning. And it occurred to me, just as a quick side anecdote, every once in a while, I’ll look at either my LinkedIn profile or a resume. You remember what those were.
Todd Merrill:
Yeah
Alan Gold:
And it occurred to me one day, not that long ago, that every single company name that I put down there, I have something else in parentheses because every one of them has been bought, sold, merged, purged, rolled up, and there’s nothing wrong with that. But often, it makes an awful lot of sense, at least at 30,000-foot level. And I think the challenge that I have always seen in being part of roll-ups and on both sides of it is what looks good to an investor PE firm at 30,000 feet doesn’t necessarily work at 1,500 feet, let alone on the ground level. You have issues of incompatible technology. You have an overlap of markets that weren’t obvious. You have any number of crazy incompatibilities or difficulties that… look, I was with a company that was technically headquartered in the UK. We were on the London Stock Exchange. The majority of the business came out of the US for many of its things, and we had a position all over the world. And we had acquired mostly through tuck-ins, a few roll-ups, something like 32 companies.
Todd Merrill:
Wow!
Alan Gold:
That’s a lot of companies.
Todd Merrill:
It’s a lot of chaos.
Alan Gold:
Well, yes, it was a lot of chaos, and we wound up. So, from a high-level corporate marketing perspective, you could tell a story of how we solve everything from A to Z, or if you’re in England, A to Z, and top to bottom, whatever you want to use for an image. But then when it got down to it, nothing talked to anything else. And we spent more money building middleware layers than we did in marketing the tools themselves, even though at an investor level, it told a great story. Now, I’ve also been part of a roll-up where that same company got rolled up into another company that was complementary, and then that got rolled up to another company. Then you take the trimming shears and you cut it all down, and hopefully, you’ve got something that is compatible and functional. But there’s a lot of chaos that generates. A lot of people lose jobs. A lot of people lose focus. There are a lot of market hiccups that go on. And so it’s really difficult to maintain momentum while you’re going through all of those changes. So, it takes a lot of care, a lot of feeding, and it has to be done intentionally, not just because it seems like a good idea.
Todd Merrill:
Yeah.
Alan Gold:
And having worn the scars from both sides of that, I can say firsthand, it’s a tough process.
Todd Merrill:
Yeah, I definitely have a few of those on my LinkedIn where it’s, you know, this company, now it’s something else, now it’s something else. Wait, it’s back to that other thing. Yeah, so it’s interesting to see what I’m an alumnus of.
Alan Gold:
Sometimes it’s even hard to know, right?
Todd Merrill:
Yeah, yeah. Well, so what do you think is going on in the market right now? Just kind of sums up the M&A landscape. It feels to me like the heady days of you get bought in 18 months with a napkin to exit by some big company, Fang, or whatever. That hasn’t played out for a while, right?
Alan Gold:
Yeah
Todd Merrill:
So, where’s the logjam? And then how do we kind of get through this? We’ve kind of all seen cycles before. What do you think is going to happen here?
Alan Gold:
Well, I mean, if I were embedded in the investor community, I would probably say good places to put my money, one thing, and the cost of the money for the investment. But from the company side of things, I think it comes down to the fact that there are an awful lot of very similar companies out there and it’s very difficult to figure out what you should pick for a winner, what you should acquire, where the value is, where the synergy comes from. And I think people are, and let’s face it, companies are made of people. And the people who are running these companies are feeling strongly about doing it on their own until they see that the market climate is right. And I think a lot of people who are, let’s call it acquisition eligible, are not comfortable with the, you know, because everyone thinks they’re a maven, right? So, everyone’s an expert. And I don’t think they think they can get the multipliers that they want to have and so they’re sitting pat until somebody comes in. You saw this in the housing market for years, you know? People thought their houses were worth more, so they weren’t going to sell. And it froze the market and interest rates dropped.
Todd Merrill:
Yeah.
Alan Gold:
I mean, there were all sorts of terrible things that happened in between, and the markets opened up again. And I think that there’s a lot of that happening at a business level that is keeping people waiting for what they believe the right value is for their baby, so to speak.
Todd Merrill:
Right. Well, and then you talked about the investor hat. Investors will tell you I can’t place money in anything at an appropriate valuation where I can make money out of this.
Alan Gold:
Right.
Todd Merrill:
And then we had a couple of unhealthy years there where things got out of control, or we got ahead of ourselves on the growth curves, and money got in at unattractive valuations. So, I guess those older companies are going to have to just grow their way out of it, right? Just kind of absorb the shock of the system, and then everything will kind of catch up again or monies got to get a little cheaper or easier to come by and loosen up.
Alan Gold:
Yep.
Todd Merrill:
That could break the logjam in a lot of ways too, right?
Alan Gold:
Yeah, exactly. Exactly. And right now, it’s kind of difficult to get money. And from a PE perspective, who wants to take on debt, you know? Who wants to take on debt in uncertain times? And it’s really unclear what the next wave is. I mean, pick an industry. It’s unclear what the next wave is. A lot of it is the uncertainty around AI, but some of it is the uncertainty around international relations, around tariffs. I mean, there’s a lot of variables right now that are causing people to say, well, let’s kind of see what settles down a little bit.
Todd Merrill:
So, you said uncertainty around AI. So, there’s that word, right?
Alan Gold:
There’s that word.
Todd Merrill:
Yeah. You know, Gartner hype cycle, we’re about to go in the trough of disillusionment, predictably, and then we’re going to kind of pick up pieces of what’s useful.
Alan Gold:
Yep
Todd Merrill:
Is that what you’re talking about? Or are you talking about some of the external competition?
Alan Gold:
No. I think a lot of it right now and don’t because it’ll just give you a headache. Google, AI, you know, AI-powered, fill in the blank, and you’ll get page after page after page because everybody says, you know, AI-powered, this is good. But at the bottom, AI is really good. AI finds patterns where the human brain can’t. It finds ways to automate, it can be used to automate activities that prevent you from doing a higher-order kind of work.
The analogy that I would use is if anyone listening to this podcast is old enough to remember the advent of calculators, you know, and how cool the floating point was for decimals. Everyone screamed and yelled that it was going to destroy Math, it was going to make kids stupid, they weren’t going to be able. And in reality, what it did was let them think about the concepts around solving a problem, and not have to get dinged and getting, you know, getting stuck on, you know, arithmetic, or for that matter, you know, trigonometry or whatever. And if you don’t know how to apply the technology, it doesn’t matter, right? And I think we’re at the same point now with AI. Yes, is it possible that AI could become our overlords and, you know, anticipate all of our moves and make our lives miserable? I suppose, but, you know, I’m not a science fiction writer. And what we do need, and I think we’re moving toward that, is finding ethical use rules, rules of engagement, strengthening privacy rules, you know, and finding the home for AI where it does the most good, as opposed to gumming things up.
Todd Merrill:
Yeah, right.
Alan Gold:
Like the old joke, you know, anybody can screw up, but it takes a computer to really screw things up. You know?
Todd Merrill:
Yeah.
Alan Gold:
You know, and so I think there’s a lot of that. I mean, I happen to be a proponent of AI, and I use it in a lot of different things. But what I use it for is to enable mundane work that I don’t have to do anymore, so that I can do the things that require thought, creativity, and a certain level of intellect.
Todd Merrill:
Yeah. Yeah. For sure. But AI is a big topic.
Alan Gold:
It certainly is.
Todd Merrill:
Leave that one there. Yeah, I was just laughing this morning. I have Sean, the shark robot vacuum.
Alan Gold:
Yeah.
Todd Merrill:
Sean was doing his thing, and I was like, you know what? That stupid robot always goes left into the same room, and it’s always clean. It’s where nobody ever goes. You know, why can’t he, you know, I was like…
Alan Gold:
Right.
Todd Merrill:
You know, and then the stupid robot decides to come in here in my office and he’s hovering around like a puppy dog, and it just vacuuming like weird things, and got stuck, and then just like, “Pick me up. Take me somewhere else.” It’s like, yeah, we’re safe from AI for a while.
Alan Gold:
Yeah, I couldn’t agree more. I couldn’t agree more. But it is a valuable technology. But, you know, it needs to find his home, just like all the other technologies that we’ve been inundated with over the years.
Todd Merrill:
Well, for sure. For sure. Well, let’s shift gears for a second. Okay?
Alan Gold:
Yep
Todd Merrill:
I got sales and marketing on the phone. So, I’d love to hear your opinions on a couple of different things. So, sales. So, I’ve got, you know, college-age sons. You know, one of them is probably a sales guy waiting to happen. What do you look for if you’re hiring that first-level sale? What makes a great natural sales individual contributor and account rep at that first entry-level job? How do you hire those people? And what do you look for?
Alan Gold:
Wow, that’s a pretty broad question.
Todd Merrill:
Ha ha ha!
Alan Gold:
But I would say, first of all…
Todd Merrill:
… yeah, what should my son be doing to get hired in sales?
Alan Gold:
I think the broad answer is it depends on the industry.
Todd Merrill:
Okay
Alan Gold:
And it really does. If you’re in, you know, a technical field, you have to have somebody who can understand the technology and can talk to someone on the other side of the phone or in person. I think that still happens occasionally. Or on Zoom or some other tool. And be able to speak intelligently reverting to, you know, the, how many can I put you down for? It works. Talk solves every kitchen crisis. But wait, there’s more. And I’ll give you six free months. I mean, that has its place, but not for the kinds of things you’re trying to sell.
If you’re selling software, if you’re selling technology, if you’re selling a professional service, you have to reflect that professional service or that technology, and you have to speak to it intelligibly. And that means, look, you have to be affable. You have to have a good presence. You have to be able to connect with people. There’s rule one of sales that will never go away is people buy from people they like and people they trust. And, you know, you’ve got second, you’ve got to be prepared to hear no much more often than you hear yes, and not let it get you down. And third, how to listen. And that for me is one of the most important attributes I look for in a salesperson. I mean, sure, if you’re selling, well, I can’t say encyclopedias because there’s no such thing anymore.
Todd Merrill:
Ha ha ha!
Alan Gold:
But if you’re selling a widget that does a limited set of functions, that’s one kind of a pitch. If you’re asking somebody to give you a million dollars for a piece of software that has a four-month implementation, it’s a very different kind of sale. But you have to be able to talk about value. You have to be able to talk about what the future state looks like for the use of our product or service. And you have to be able to tease out the problems that they have now. And so if you can be a little bit of a detective, you know, I mean, you don’t have to have CIA-level skills, but the CIA could use some CIA-level skills, but that’s a separate issue entirely. If you are able to tease out the problems that someone has, it’s a lot easier to find a way to solution it. So, it takes creativity. It takes the need to listen. It takes the ability to understand what it is that you’re selling. And we’re not talking about telephone hacks. We’re not talking about call centers, which have got to be the third rung of hell for people in a job is just smiling and dialing, you know, for elbow braces and knee braces and all sorts of other crazy stuff.
You know, we’re not selling supplements, but for those who want to do that, you still have to understand the benefits and you can’t be too pushy. You have to know when to give and take. So, I mean, all those things really go into making a good salesperson, you know, and people tend to think of salespeople as pretty low on the ladder of businesses. Right? And I disagree entirely. I think it’s a lot harder for someone to sell a product credibly and to get somebody to say, yes, I’ll buy it. Than it does for somebody to do, with no disrespect to my friends in the accounting world, to do a spreadsheet and look at payables or receivables. It takes a lot of work and a lot of effort, and you’ve got to be extremely resilient.
Todd Merrill:
I think as a technologist, I appreciate sales.
Alan Gold:
I’m with you. Absolutely. It’s hard, man. It’s really hard to do. And you have to hire somebody who understands it. I mean, in the pharmaceutical industry, I mean, we all know the jokes about pharma reps, right? I mean, they recruit from pep squads. They recruit from cheerleading squads, men and women. And there’s a certain personality and delivery style that they seek on knocking on doors and getting in to see doctors. Now, that’s changing a little bit, but it’s still the profile that a pharma company picks for an outside salesperson.In technology, I think it’s a very different thing because technologists and most companies buy very differently, deliveries too. And that world, I think, has changed a great deal. There’s much more pull than there is push.
Todd Merrill:
Yeah. Let me kind of throw a weird idea about that. So, a couple of us were talking the other day about getting early seed funding for a startup in general. So, a lot of people have that problem. And what we kind of came down on is it’s easier and harder at the same time to do a startup because you have all these tools. You don’t have to go buy a server anymore. You can go to AWS and just rent one. There’s marketing automation. There’s sales automation. There’s all this stuff. And then we kind of said, well, yeah, it’s so easy to get some traction for very little money, but then you have to do all this stuff and be a master of all these domains. Investors are kind of sitting back going, “Well, why can’t you get to a million in revenue before I talk to you for your first check?” And then you go, “Well, yeah.” But it requires such a high level of mastery of lots of domains. You know, a kid out of college that’s just been to one, that’s a good salesperson or a good coder or a good whatever, isn’t going to make it, right? You have to have so much mastery. Is this kind of what we’re seeing in sales?
We used to call them order-takers and salespeople, right? And then the complex enterprise sales would, you know, you have marketing over here and you have leads and they were carefully… somebody went through those and handed them to you. And then you’d have your sales engineer and then he would bark like a chihuahua for a couple of hours, you know, and then your job was to sit and play poker in the back of the room as the enterprise sales account rep, right? And there’s relationships and the three-martini lunch and all that. And now that’s not how it works anymore, right?
Alan Gold:
Yeah.
Todd Merrill:
And then we’re all expected to level up and become so masterful over so many domains. You don’t have that sales engineer with you anymore. Not a lot of times, right?
Alan Gold:
Yeah, that’s very true because companies, especially early-stage companies, out of necessity have to be lean. So, you have to be able to wear multiple hats. But if I could go back to a point that you made because I think it’s an important message to get across and coincidentally, it’s something that I write about on my LinkedIn site. I write articles on these sorts of topics so feel free to reach out. But the normal path for somebody with a startup, right? Somebody’s a big-brain idea. Oh my God, this is going to be the greatest thing since sliced bread. Everyone’s going to love this. They go off and build it. And maybe they get a lighthouse account with their cousin, Marvin, you know, down the street somewhere and he puts it in. “Yeah, this is great. It’s wonderful.” And so there’s kind of a false positive there. This is great. And the next thing they do is they go off and, you know, they hire some sales guy, you know. Maybe the guy is in the industry, maybe he’s fresh out of school. Maybe it’s his second cousin, you know, who was willing to do it on an internship basis. He comes in and guess what? He falls over because there is no such thing as one person knowing everything.
I mean, there may be some exceptions to the rule, but you can only do things at a skim-coat level if you’re trying to do all things. So, the first thing that happens on the sales side, he says, I need marketing support. Where am I going to get leads? Because you can’t cold call. You’re not a full-of-brush salesman walking down the street, knocking on doors. That’s how they started at IBM and Xerox. You started literally, here’s your bag. You’ve got this block and you go up and down the buildings from, you know, floor two, all the way up to floor 212 if there was one, and you knock on every single door and you sell your devices. That doesn’t work anymore, you know? And so you need to have some level of expertise, whether you’re renting it with a fractional, whether you’re hiring an agency, but you have to have some capability to develop awareness to get that to the salesperson to be able to follow up with. And the founder may speak with passion to a handful of accounts, but that founder can’t go on every sales call. That founder can’t also then be managing the leads. That founder can’t also be driving product development to improve it because let’s face it, nothing is ever finished by the time a founder is ready to go off and sell it. And you can’t have a salesperson constantly being shadowed by the founder because the salesperson will never tell it the way the founder does. And that doesn’t make it wrong, it just makes it different. And so, you know, for a salesperson and to be ready for a sales organization, you have to be able to map out what the story is. You have to be able to map out the value proposition. You have to be able to map out the targets and the benefits and how this is going to change someone’s life. And then you have to have the chops to be able to demonstrate that.
And I think you see that all the time now with, you know, whether it’s an AI tool, whether it’s a CRM tool, whether it’s a drawing tool. I mean, whatever it happens to be that you want to sign up for is you wind up with an onboarding call or two with somebody taking you through, but it’s usually the salesperson until you grow to a certain size, you know, because it’s top-level information that you’re helping them understand how we can do these things. That’s why 30-day free trials, call us when you’re ready, doesn’t work. It can only get to around day 25. They played with it for 10 minutes in the beginning. They got really busy. They weren’t 100% certain how to do something. So, they put it aside. Then the sales guy calls on day 25. “So, what do you think?” He goes, “Yeah, I haven’t really had a chance to play with it. I have another 30 days.” You know, and the sales will never get there. So, you’ve got to have the chops as a salesperson to be able to nurture that lead. And sometimes that means taking them through and teaching them the hard stuff until the organization grows sufficiently to be able to have that part of a sales process so that you can go off and just get to the next one.
Todd Merrill:
That’s a lot of skills you just mentioned.
Alan Gold:
That’s a lot of skills.
Todd Merrill:
And then some of the easier skills, you know, the junior skills, take the order, have that initial phone call, figure out who to route it to. That’s all software now, right? Or it’s all a website or RevOps or something.
Alan Gold:
Mm-hmm.
Todd Merrill:
And then so you kind of, you know, where’s the entry level for all of this? How do you, you can’t go from zero to mastery of all of that, you know, in a year or two, right? You have to, you know, are you born with it? You know, how do we manufacture the next generation of folks like you that get it? You know because it’s getting reps in, it’s hearing no, growing your thick skin, right? But also have empathetic listening skills and figure out how to tell the message in a way that they’re going to get it and be receptive.
Alan Gold:
Yeah, and that’s a great question because most people pull the information they want. I mean, I’ll use trade shows as an example. They still do exist and people still go to them. But back when I was standing on the show floor, which I’m delighted to never have to do again, because there’s nothing worse after a while, your back starts to seize up, you know, and you’re tired of talking. I’m not that social. But, you know, this was the once or twice a year that you came to a place to learn about stuff, you know, and now you don’t have to do that.
Now people go to a trade show or a conference for that matter, and it’s a reward for having done a good job. You get to take a trip and find out something new. To your question, when I hire an entry-level sales rep, I look for the raw skills and the ability to learn. Sure. It’s ideal if somebody has… because we’ve been talking about tech, you know, if somebody has a tech background of some sort or a marketing background or a sales background of some sort, but I would rather have somebody learn about the product and shadow phone calls from my first sales rep, whether that’s the founder or whether that’s the existing sales rep, shadow the calls, do a couple of tag team calls, and then let them out on their own from scripting. And then they develop their own style. You know, it’s very little … I mean, other than rocket science, most of the stuff that we sell isn’t rocket science.
Todd Merrill:
Yeah.
Alan Gold:
You know, it’s because especially for non-specialized skills, for user-facing applications, it’s all about what it does for you. It’s all about the future state versus the as-is state, listening and identifying problems, and then talking about how this will change your life. And those are skills that any bright person out of school could learn, you know?
Todd Merrill:
Yeah
Alan Gold:
You don’t have to be an expert in it because it’s the classic question, how do you get expert? How do you get experience if nobody will give you a shot? And I’ve had an extraordinarily high success rate in bringing people in who I think have raw talents and helping them through learning the specifics of it all, letting them stumble a little bit, giving them the easy stuff, starting them on lead qualification, just to kind of gather information and then have them shadow on calls. It all works. And then they self-select. You know, they may decide it’s not something I want to do. I want to go elsewhere. Or they may decide this is great and they grab a hold of it and sort.
Todd Merrill:
Let’s go up the growth curve a little bit. Okay. So, at some point, you’re successful. You have several sales folks that know what they’re doing and you have reliable revenue coming in. Now you need that VP or C-level sales personality.
Alan Gold:
Yeah.
Todd Merrill:
How does the organization have to change and grow in that $20 to $50 million recurring revenue phase of growth where you’re setting up systems, you haven’t quite figured it all out yet, but you kind of… it’s deterministic, right? It’s a matter of money and time and setting it up properly. What does the set it up properly mean or how does that work?
Alan Gold:
Sure. Well, again, I can only speak in generalities because it varies by industry and really the DNA of a company. I would argue that you can’t get to 10 million without having a lot of differentiation and having some basic systems in place. I mean, just you can’t because even if they’re $100,000 deals, which is unlikely, if they’re $50,000 deals, divide that into 10 million, that’s a lot of deals to keep track of without systems.
Todd Merrill:
Yeah
Alan Gold:
But when you do bring in somebody to manage a sales function, there are two fundamental changes whenever that happens. One is everyone in their pet duck shouldn’t be going down to the individual sales rep to send them off in one direction or another or give them talking points or drive them forward. It should be that VP of sales and presumably in conjunction with their counterpart on marketing. And second, never, ever, ever, in my experience, promote from within to a head of sales.
Todd Merrill:
Oh!
Alan Gold:
Never take your top sales guy, at least this has been my experience, and make them the leader of a sales team because what makes the best sales guy in the world is almost the opposite of what makes a great sales manager.
Todd Merrill:
No kidding. Okay.
Alan Gold:
Because well, I mean, think about it. What makes a great sales guy? The ability to connect with a client, be able to talk through objections, the ability to know when to push hard and when to back off and to get out in front and really be the leader of the pack and dive on it and really push hard and get somebody to close a deal. The last thing in the world you want to do is have them managing people.
Todd Merrill:
Ha ha ha! Okay. Make sense, yeah.
Alan Gold:
Because if you bump them up to that, right? You can’t have them pounding on the sales guy to close things. Well, I used to do this. Why aren’t you doing that? Why aren’t you doing it my way? This doesn’t work. That doesn’t work. Or I thought you said you were going to get it closed on Tuesday. Now, that’s not true. You might want to have somebody who pushes. You said Tuesday. It better be Tuesday. When we do pipeline reviews, my VP of sales, my favorite VP of sales had three categories. One of them was I would wager my house on it. The next one was I would wager my spouse. And the third one is I would wager my children.
Todd Merrill:
Oh, God!
Alan Gold:
I mean, that’s exactly it. That’s how she would set up the pipeline. And she also used to tell people to camp out. If a customer has committed to a deal, then they’ve committed to a deal. And you’ve put that number in there. And you’ve built a relationship where they have a responsibility to follow through on their promise. So, she used to send them to camp out. Literally, she would send them to a campout. And they’d sit in the lobby and say, “I’m here to meet with”, you know, Todd Merrill. “Is he expecting you?” “Oh, I told him I’d be here so we can finalize the contract.” You know, and there were times when they sat in the lobby for three days. I mean, they went home at night.
Todd Merrill:
Yeah
Alan Gold:
And I know that those are extreme examples. But the things that make you a good manager don’t necessarily make you a very good individual contributor. You see that often in the software development world. You see that very often in marketing as well because you’re asking people to deal with personalities on your team that are not episodic. You know, with a customer, there’s a beginning, middle, and an end to the relationship. Right? When you’re managing salespeople or whether you’re managing marketing people, there isn’t a beginning, middle, and end. There’s an ongoing. And your job is to make them do as well as they possibly can do and that’s very different than you do as well as you can possibly do. So, it takes a very special person to be able to make that step up. And in my experience, that is the exception rather than the rule.
So, I’m sure our listeners will come up with 50 different examples of how that’s worked positively for them, and I’ll accept that and apologize in advance. But my experience has been its very different personality types. Leadership styles.
Todd Merrill:
Yeah. Well, it’s interesting. And then where do they come from? You know, and then I can see a problem here where nobody’s getting entry-level jobs anymore. And then you’re expected to go right to the very sophisticated level of operating.
Alan Gold:
Yeah
Todd Merrill:
And then it’s like another big chunk to go to the next level where, you know, just because you’re good at something doesn’t mean you should be the boss of it, is what you’re saying?
Alan Gold:
Absolutely. And, you know, at the entry-level side of things, I think entry-level really is changing in a lot of categories. My son is a software developer, and they use AI to do some basic code work. And I would say early-entry developers, just like early-entry copywriters on the marketing side of things, they’re going away because they’re, you know, and it takes away the learning curve. And so arguably, people are going to realize that they no longer can build a pipeline of people or fill those roles as people move up the ladder or the education system is going to have to add those baseline skills to be able to support those. But if they’re going away, I mean, I don’t think this is a problem that’s being thought about broadly, you know, about what happens to entry-level people if technology is taking up those roles. And I don’t sit here with an answer for you, but it is absolutely an issue. It has to be considered because how do you get experience without having experience?
Todd Merrill:
Yeah. It’s kind of like, you know, like manufacturing. Everybody is talking about how manufacturing has a shot at coming back here. It’s not going to be a bazillion low-wage people on a shop floor if it’s in America. It’s got to be heavily industrialized robots and automation. Machines.
Alan Gold:
Absolutely!
Todd Merrill:
And you’re going to have a team of electrical engineers and folks that can troubleshoot electronics.
Alan Gold:
Yep.
Todd Merrill:
And then from there, you know, it’s going to be the robots doing the work.
Alan Gold:
It’s great.
Todd Merrill:
So, it’s a different world. It’s a different level of sophistication. It’s hard. It’s a hard problem. And then what does everybody do? That would have been in manufacturing?
Alan Gold:
Yeah. I mean, there’s a reason why manufacturing was pushed offshore, you know? And it was pure and simple about cost, you know? And I mean, I’m all for everyone having a living wage. I think that should be a basic right for all of us, but our economy is not built around and never has been built around high-wage, arguably, manufacturing. It just simply never has been. You know, people forget that. I mean, the big push to create unions. Now we’re going far afield, but the big push to create unions was to develop living wages for the employees, safer environments, and certain frameworks around work hours and conditions and so forth. And it’s been very successful at that.
And US manufacturing is highly productive. But if manufacturing comes back, to your point, it’s not going to be, if it was 100 people on a particular line, it’s going to be five people or three people on the line, and the rest of it’s going to be robots and automation. And so, it’s not going to bring back, you know, $100 an hour. You know, one of the things that were a longshoreman strike, there’s been a lot of longshoreman strikes, and what struck me was when they settled the strike, there was a clause in the settlement that said that there would be no or limited automation. Arguably, you know, where in other ports where there wasn’t a strike, these things are highly automated. Go to Singapore or go to Hong Kong or go to any number of other ports, even LA, there’s an awful lot of robotics moving things around. You know, there aren’t people to make accidental mistakes. There aren’t people to get hurt.
There’s one guy in a control room, arguably a whole bunch of these systems. And so, you know, I mean, the unions recognize that as they should, that the model that we have now is going to evolve and that’s no different than how do you get entry-level salespeople, and do you even need entry-level salespeople, as if we bring manufacturing back to the US, what’s it going to look like?
Todd Merrill:
Let’s switch over to a different topic.
Alan Gold:
Yeah
Todd Merrill:
This is fascinating. I got to think about it. But I mean, it’s a little depressing, you know, we’ve gotten up the curve, right? So, there’s going to be a demand for people who can operate at a sophisticated level.
Alan Gold:
That’s right.
Todd Merrill:
But I worry about my kids, right? How are they going to do this? And then, you know, it’s a weird situation in the world right now.
Alan Gold:
Yeah, it absolutely is but it’s important for us to all be thinking about it. It’s important for your son to think about it. It’s important for leaders to think about it. It’s important for VCs and private equity firms to be thinking about what the nature of business is going to look like because that’s where they ought to be investing their money.
Todd Merrill:
Real quick, I want to talk to you about marketing. So, we said sales and now marketing. So, AI is a big thing. We talked about that. AI is disrupting a lot of marketing types of activities. There is a lot more information in the market, is a kind of polite way to say it.
Alan Gold:
Mm-hmm.
Todd Merrill:
And then it’s our job to go through that information and cut through and get to the signal. You know, what’s kind of going on in the marketing world right now? How should we be thinking about marketing? It’s been changing quite a bit lately with a lot of automation and AI that has come in.
Alan Gold:
Yeah, that’s a great question, Todd. And I guess from the long view that I’ve traveled on marketing, I think one of the most interesting aspects of things is that marketing has become much more specific, and to a degree when people think of marketing, they’re not thinking about marketing. They’re thinking about one aspect of it. And I would say, broadly speaking, digital marketing. These days, if you talk to most companies and they say we need marketing, they think about pay-per-click. They think about ranking on Google. They think about automation tools and email blasts and webinars, you know, and stuff that’s just driven around that. What they don’t think about is strategy. And that is one of the things that I have seen fall to the wayside because it doesn’t have…we take a step back. Historically, there’s always been the question of how to monetize, i.e., justify marketing. How do you say what’s the ROI on my marketing spend? And I would argue, you take marketing away and see what happens to your sales and subtract the two numbers. And that’s your marketing lever. Now, that’s silly, of course, in real life.
Todd Merrill:
Yep.
Alan Gold:
But I think what has happened in many ways is the pendulum has swung to something that I call looking at the wrong side of the decimal point. And there’s an attempt to monetize down to individual event level, an individual email, an individual click to find out how much value was generated from that activity. In reality, money buys from one thing. Even if it’s just something to buy your kid at home, you look at something two or three times and decide whether or not you should do it, especially these days when you can’t be 100% sure what you’re clicking on. So, you have to be a little bit cautious. But wherever I have been, whether it’s been in my professional, my full-time CMO work, or in my consulting work, and maybe even especially in my consulting work, the missing piece when people ask about marketing, it boils down to, I’m not growing like I should, I’m not giving the revenue I need, my margins stink. How do I get my, you know … we keep losing deals. And a lot of it always comes down to strategy.
Who do we want to be? What’s the voice we want to speak in? And I don’t mean from a swishy brand perspective. I mean, what do we want to tell the world that we do better than anybody? And if you can’t answer that question, you’ve got to ask, why are you in the business? And why aren’t you doing something else? Which raises other kinds of discussions to have. And so all of that requires strategy. And it has to be linked to the sales side of things, is what do we need to have for revenue? How do we think we can get there? And what are the tools and activities we need to do to get to that revenue number in a profitable way? And that’s the piece that, in my experience, a lot of companies don’t leverage when they bring in marketing. They bring in marketing to do all these tactical, executional things. And even if you’ve got one person there who’s coordinating all of it all, it’s not necessarily doing things with intention. It’s doing things because I’ve hired an agency to do pay-per-click (PPC). I’ve hired an agency to redo my website. I’ve hired an agency to do SEO work to improve my rankings on Google, which, by the way, with the advent of AI, is going to become less and less useful. Anyway, that’s a completely different conversation. So, to me, the biggest miss winds up being the strategy piece. And that wasn’t the case 10 years ago. Ten years ago, it was about strategy and then applying execution to that strategy.
Todd Merrill:
Okay.
Alan Gold:
Now, because so many tools are already made, that’s the downside of a founder or president or a VP of sales or a VP of marketing, so-called, because they could write well. They became the de facto VP of marketing, which happens in startups. You know who you are.
Todd Merrill:
Right
Alan Gold:
It jumps the category of strategy. And so just doing stuff, you could spend an awful lot of money doing stuff. You might even get some results, but it isn’t sustainable because you don’t even know why you’re doing it right. You don’t know what you could be doing differently. Why are you spending this money? Could you do things in a different way? And none of that ever gets done.
Alan Gold:
It’s emotion, not progress.
Alan Gold:
Exactly. In a lot of cases, absolutely. And a lot of money is being spun out.
Todd Merrill:
It’s interesting to see, longitudinally, what’s changed over the years. And it’s interesting that you would say strategy is now being overlooked because you’ve got leveraged points for these tactical things. It kind of makes sense.
Alan Gold:
Mm-hmm.
Todd Merrill:
But when you say it out loud, it’s like, oh, yeah, I guess that’s right. And then, okay, so let’s put a concrete example around this. So, you’re the co-founder of a little startup company, and you get white piece of paper. You got a solid product. You don’t have to worry about that. You’ve got good technology. You think you know who you’re going after. What’s the play? How do you set that up as a startup? And then we’ll kind of take it as an older company trying to turn it around too. And how does that change? So, while startup, what’s the white sheet of paper? Sales marketing, rev ops, you’re the guy. You’re the co-founder. What’s your favorite playbook? Or what should people be thinking about in that seat right now?
Alan Gold:
Sure. Well, first and foremost, you need to know what your product is up against. Because I would argue that most of the time, other than a vague notion, and there are definitely exceptions. I want to be really clear about that. There are a lot of founders who have this vague notion of a product that might improve over something or other, but they haven’t really done a deep dive into competition. So, they’ve built something. Let’s assume they even did that and now they’re ready to go to market with it all. How do you tell the story that’s different? So, step one is how do you tell a story that’s different than the people who have products like yours? It’s really tough unless you’ve got a lot of money behind you. And believe me, I’ve been there. It’s really tough to create a new category. If you’re a category of one, you spend all of your time saying, well, it’s kind of like this. But at the minute you have to say, it’s kind of like this, but, you’ve lost them because they’re going to think of it. They’re going to think about it as the category that they’re familiar with. So, you can’t create a category.
What you can do and have to do is talk about why you’re different and why you’re better and the value that you bring. So, step one is getting that messaging down. Before you start selling anything is figuring out what your reason for existence is. And assuming you can do that, then you figure out what the best way to deliver that message is. And it may not be with a physical salesperson. It may be an e-commerce play. It may be a consultancy play. It may be a partnership play that you’re the technology behind or the enabling technology behind any number of other broader services.
So first, you have to really think about where you sit in an ecosystem, where you sit against your competitors, where you sit in the broader world that you’re going to take your product and put it into. I realize I’m looking at this from a very tech-focused kind of world because I think in software blocks.
Todd Merrill:
Sure
Alan Gold:
But it’s equally true. I mean, if you were in the buildings’ material world and you developed a really cool kind of concrete, and there are companies working on this now that have a much lower climate change footprint, a much lower energy cost to build it. Some of it is recycling. Some of it is adding in other mixtures, things that I don’t really understand. I just think it’s cool.
Right? And what’s the first thing you’re going to do? You’re not going to come right and say I’ve got concrete just like somebody else does. You’ve got to figure out that I’ve got better concrete that meets the same kind of standards. This is where I sit for pricing. These are the people to whom I have to sell this and convince them that it’s a better concrete for them and it tells a better story. It might give them a LEED certification. That’s a climate-friendly certification for energy efficiency. It might give them a quicker time to market. Whatever those advantages are that applies across every industry that you could possibly think of. So, you have to place yourself. That’s step one before you do anything else.
You have to figure out how to get that message out. Right? You know, yes, everybody thinks well, build a website. Well, there’s more to putting up a website than putting up a website. You have to think about what you want to say because that’s your billboard to the world. That’s your story to the world. You have to be very intentional about it. The problem is that it’s really tough to differentiate an agency that will do a really good job for a website at $5,000 versus $50,000. It’s really difficult to get your arms around what the differences would be in that. So, everybody opts for some low-end building tool because they want to be really prudent with their money. That is not a bad solution, it’s just, you just have to be careful.
You still have to figure out what you’re going to say and how you’re going to tell the world. Once you have those things in place, then you can start thinking about bringing in the appropriate sales mechanism. Whether that’s an e-commerce storefront, whether that is literally a guy with a clipboard going around to developers and construction companies, or whether that’s getting a salesperson and reaching out to a curated list of people for whom this might be a useful product. And then you start to blossom out from there. But it’s really all about telling the story and getting the right mechanisms for that product where it sits in the world.
Then you can add around the edges. Then you add one salesperson. Then maybe you bring a marketing person to coordinate activities. What you don’t want to do as the founder is hold on too much to too many things. Another one of my phrases is if two of us are doing the same job, one of us doesn’t need to be here. That’s a challenge sometimes in the founder’s world because they’re used to evangelizing their story, and that in itself may be the best solution to get things started. Maybe that’s what you do. You center around that story. Then you hire people who can emulate that story, where you take that story and you put it in the context of the industry.
Todd Merrill:
Very cool. Well, let’s take a different case.
Alan Gold:
Mm-hmm.
Todd Merrill:
So, there’s a company that’s been out there for a while, kind of stalled out $15, $20 million a year, not really making a whole lot of progress in the market and wants to grow and doesn’t understand what happened. What does somebody like that, what should they be thinking about? How do you attack a problem like that?
Alan Gold:
That’s a really interesting problem. It’s one that I’ve had to deal with several times in my career. It’s not an easy one. Frankly, it starts with some introspection. There’s a saying that if you’re not growing, you’re dying, right? So, if you’re at $15 or $20 million and you’re kind of stuck there, there’s a reason why you’re stuck there. Step one is understanding the market that you’re in, understanding the dynamics that have kept you there, and understanding the people who are buying from you. I find it useful talking to people who have stopped using you and understanding what your competitors are doing that may be the same, or maybe they have shifted emphasis.
I mean, kind of a silly example, though a useful one for some parts of our listening audiences. Think about Salesforce. Other than the fact that they have a multi-billion-dollar marketing budget, literally, they have been absolutely brilliant from the beginning at catching a wave and recasting themselves in that wave from the very, very beginning. They picked up on CRM before CRM was a thing, and that’s how they talked about themselves. They talked about themselves being a cloud provider before anybody else talked about cloud provider. They talked about themselves being marketing and sales before anybody else talked about it, and they really jump on that quickly. So, understanding what the ecosystem looks like is always step one, you know? Am I in a crap market? I guess I can say that, right? Am I in a market that’s going away? How’d you like to be selling faxes?
Todd Merrill:
Yeah. I got an email for that the other day. Hey, how’d you like to be our channel partner? It sell faxes?
Alan Gold:
Exactly.
Todd Merrill:
No, thank you.
Alan Gold:
Well, let me tell you something. And yes, in certain markets, because there are all sorts of weird confidentiality things, they think faxes are better, especially in medical areas and so forth. But way back, this is a story from ancient history, FedEx, known as FedEx at the time created something called ZapMail. It came and went so fast. It was kind of a same-day delivery, the modern-day same-day delivery. They could get a letter to you the same day. It was fax technology. Two months later, if that, after this, God only knows how much money they spent on that, the first commercial fax machine came on the market.
Todd Merrill:
Okay.
Alan Gold:
That took an entire category, swirled it right down, and it went away. And some markets are like that. Some markets become subsumed into others because the footprint just wasn’t big enough to be sustainable. So, I would look to see what I’m doing as a company in that marketplace, whether or not it’s still sustainable, whether it’s a diminishing market, whether my competition has migrated out. And if they have, what have they migrated to? And then there’s a decision to make. Do you modify what you’re doing? Do you do a complete flip over to a different technology?
I spend a lot of time looking at adjacencies. When I work with a company as a consultant or in my CMO days, I would look for adjacent markets. Markets that have similar characteristics but have more white space, or if you prefer, green space to expand out into where there’s nowhere near as much noise. I would not want to be an agency, a digital agency. There are approximately 54,000 of them in the US right now. I don’t know how you get differentiation in that. And I just looked that number up for an article I’m writing.
Todd Merrill:
Wow!
Alan Gold:
So, if you’re one of a gazillion, that’s one thing. If you’re one of only three, that tells you something too. And I think the next step in the process is a result of what you find. And it may be that we have great core strengths in A, B, and C. Those can be leveraged in this market. I had an experience not too many years ago. I worked for a company out of Toronto. We were, in fact, one of the few companies that took ourselves private. We’re about a $50 million company. And our board gave us the challenge. We were in a dying market. And I could see, I mean, it was still thriving. It was a high margin. It was great. But you could see the end of the road. Or if you prefer, you could see the oncoming headlight and there was no question about it. So, we had to figure out what was happening in the market that was an adjacency to what we do. And we found a series of capabilities that were on the growth curve that a lot of people didn’t know about, but built off of our core competencies, and we migrated there. In a three-year period, we created as perfect an X function as you could possibly imagine because they said we can’t lose revenue or margin.
Todd Merrill:
Wow! Stuff to do.
Alan Gold:
Yeah. Stuff to do is exactly right.
Todd Merrill:
Trapeze thing, right? Like, go to the next bar and don’t slow down.
Alan Gold:
I didn’t know I could do a split, but I did.
Todd Merrill:
Okay
Alan Gold:
And it really hurt, but we did it, you know?
Todd Merrill:
Wow!
Alan Gold:
And your results may vary, but we did a really good job of finding that adjacency and making that shift. And if you’re in it, it’s really tough to see where you could go with that. But if you’ve been at $15 or $20 million for a few years, there’s a reason. And it could be as simple as you have the world’s worst sales team. If you haven’t figured that out in three years, well, maybe you have the worst management team in the world. So, you really have to tease it apart. But most of the time, it’s more about what you’re offering just isn’t that interesting anymore. And so you have to find a way to make it interesting.
Todd Merrill:
It comes back to strategy.
Alan Gold:
Exactly. It comes back to strategy.
Todd Merrill:
Strategic direction.
Alan Gold:
Yep. And if I could make one point about strategy, Todd, that shouldn’t be missed. People cringe when they hear strategy. They think of consultants. Sorry to my friends at McKinsey. They think of McKinsey and Deloitte and Bain and all these people that come in, suck your input out of your brain, and then present you a slide deck with all the things that you said if you would ask for a check for several million dollars and go away, leaving you to implement. I mean, that’s really the model.
Strategy doesn’t have to be this all singing, all dancing, gigantic capital S thing. In fact, if it is a hundred-page report, it’s useless, you know? Strategy is looking at the as-is state and mapping out a plan for what the future state should look like. I mean, it’s as basic as that, but it requires an evaluation process. It requires thinking about things. It requires looking at market factors, technology factors, and people factors. Even long-term, depending on your market, long-term socioeconomic factors. Most companies consider that a luxury. We’ve got a smart management team. We can think about it ourselves. Well, if you’re in your third year of being 15 to $20 million and you can’t figure out how to get out of it, there are a lot of questions that you should be asking.
Todd Merrill:
Yeah. You’re missing something, or you’re too comfortable and unwilling to change.
Alan Gold:
That’s right. Or your market won’t support any more than that.
Todd Merrill:
Yeah. Well, yeah. And you got to find another market or an additional market or something.
Alan Gold:
That’s right.
Todd Merrill:
Neat. Well, let me ask you about traveling. It’s all about getting out in the world and making things happen, right?
Alan Gold:
Yep
Todd Merrill:
I know you’re a traveler and you’ve probably got some really cool travel stories. Do you have anything you want to share with us about this travel or travel in general?
Alan Gold:
Well, first of all, after 35 years of flying almost every week around the world, I can tell you that I’m a very happy man that I don’t fly much more than a few times a year now. And God bless Zoom because I can do the laundry while I’m working. So that’s a plus.
Todd Merrill:
Ha ha ha!
Alan Gold:
But I’ll tell you, I have been very fortunate. I mean, I’ve been very fortunate to work all over the world. I’ve worked in Japan. I worked out of Canada for years. I have been all over South America. I’ve been all over Europe and all sorts of strange places, too. I’ve even been in Finland, for heaven’s sake. And two stories come to mind. One was being in South Africa, in Cape Town. And Cape Town is well-known, especially in its nature preserve down by Cape Point, where you overlook the ocean. They have a very unruly troop of baboons that have been there for ages and ages. And they are thieving little extortionists, buggers, and they’ve been known to rip things out of people’s cars and rip sandwiches. And so I had been warned about it. And so I had driven down there with a colleague to go see what Cape Point was all about. And this baboon came up to the window, looking for his entry fee. And I rolled up the window. Just like a person, very calmly walked over in front of the car, climbed onto the hood of the car, squatted, looked over his shadow, looked over his shoulder at me, and went. And then finished, looked over his shoulder again, and sauntered off. And I kid you not. And my second story was…
Todd Merrill:
… o plomo
Alan Gold:
Yes. How do you explain that to the rental company?
Todd Merrill:
Yeah
Alan Gold:
And the second one, which was a little bit more scary. Oh my God, I’ve got several. I got detained. I used to do a lot of work in Colombia. And unfortunately, at the time, I had a mustache that made me look even more suspect than I do now. And I went there with some frequency. I was working with Unisys at the time, just so you don’t think I was doing something untoward. And I had to get this non-resident business visa, and I went through all this stuff. On one trip out, I got detained by the Colombian immigration people, who happened to be big scary people in fatigues with machine guns.
Todd Merrill:
Ha ha ha!
Alan Gold:
Because I was on a codeshare flight.
Todd Merrill:
Okay
Alan Gold:
And they didn’t recognize the flight. It was an American Airlines flight, but the flight in Colombia was flagged as whatever the airline was flight. And they took me in armed guards, and they interrogated me right down to the steel table and the light dangling over my head.
Todd Merrill:
Oh, man!
Alan Gold:
My Spanish isn’t so great. And their English suddenly became non-existent until finally, we worked it all out. After I sweated about 12 pounds into my shirt, and left. And all of a sudden, their English became impeccable. And we left. And I have others too, but we’ll save that for another podcast.
Todd Merrill:
Sure. We’ll have you on again. And which airport are you flying out of these days?
Alan Gold:
Oh, typically, I’ll fly out of Boston. I live just before the coast of Maine in New Hampshire now.
Todd Merrill:
Okay
Alan Gold:
But I fly out of Logan. But I lived in New York, flew out of JFK and LaGuardia all the time. So I did a lot of LAX, JFK stuff.
Todd Merrill:
Oh, my God. Yeah. God bless you for that. You survived.
Alan Gold:
Yeah, barely. I have no hair, but I survived.
Todd Merrill:
Yeah, there you go. Well, Alan, it’s been great having you on the show. And I always enjoy talking to you. How can people follow up with you after this if they want to hit you up on the internet?
Alan Gold:
Oh, that’d be great. My email always works. I’m Alan, A-L-A-N dot G-O-L-D at TechCXO.com. You can find me on LinkedIn at Alan Gold or Alan E Gold, and I’m pretty easy to find there. And I’m on Instagram. But mostly, I follow people’s recipes and my wife’s art. But you can do that, too. And that’s Alan. Let’s see if I can do this right. Alan E. underscore Gold. Don’t ask me why.
Todd Merrill:
We’ll put it in the description below.
Alan Gold:
Please. But happy to expand on anything anybody had an interest in talking about.
Todd Merrill:
Well, and it’s been great having you.
Alan Gold:
Thank you.
Todd Merrill:
Bye for now.
Alan Gold:
Bye for now. Thank you.
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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