Episode Summary

Alan Gold, a 30-year marketing and sales veteran, discusses his career spanning Wi-Fi launches, speech recognition, and AI tools across startups and M&A. He covers current market uncertainty, the shift from sales tactics to strategy, AI's impact on entry-level roles, and why promoting top salespeople to management typically fails. Gold emphasizes listening skills, differentiation, and strategic thinking over tactical execution.

Pull Quotes

On the fundamental mistake companies make when structuring sales leadership

“Never ever ever in my experience promote from within to head of sales. Never take your top sales guy and make him the leader of a sales team. What makes the best sales guy in the world is almost the opposite of what makes a great sales manager.”

“The biggest miss winds up being the strategy piece, and that wasn't the case ten years ago. Ten years ago it was about strategy and then applying execution to that strategy. Now because so many tools are already made, it jumps the category of strategy and so just doing stuff.”

On the core requirements for successful salespeople

“People buy from people they like and people they trust. 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, you need to understand how to listen, and that for me is one of the most important attributes I look for in a salesperson.”

On diagnosing stagnant company growth

“If you're stuck, there's a reason why you're stuck there. If you're at fifteen or twenty million and you're kind of stuck there, step one is understanding the market that you're in, understanding the dynamics that have kept you there, understanding the people who are buying from you.”

“How do you get experience if nobody will give you a shot? I've had an extraordinarily high success rate in bringing people in who I think have raw talents and help them through learning the specifics of it all. Let them stumble a little bit, give them the easy stuff, start them on lead qualification.”

Transcript

Hi welcome to Tales From The Sky Lounge, 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 the word out.

Today's guest in Sky Lounge is Alan Gold. Hi Allen, hello Todd, great to be here. Great to see you again. Hey Allan, who are you and what are you working on?

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 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 badly looking barcode. I work with that, it's called PDF417, and I've been involved in speech recognition from its earliest days all the way up into different kinds of AI informed management tools. So it's been an interesting journey. I've been in startup companies, I've been on both sides of mergers and acquisitions, have taken companies private, have taken companies public, and about eight years ago I decided to step out of the M&A world and become a consultant on my own with a number of different long-term clients, everything from pharma to social services, and joined our company TechCXO about 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 on an account and also to have a peer group to share ideas and get ideas from. That's where I am now.

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. You know, I at the end of the year talk to lots of funds and you get the updates from all these companies. 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. You know, I got a lot of information from some of these folks in our adventure world. Hey, we sure do need some healthy exits to free up some of this cash to get the engine going again. Everything's cyclical. What are you seeing out there in the world as far as M&A and exits and that kind of thing in general?

Well, it's a bit of a mix and as you implied, it's frankly an uncertain time. I mean, you know, 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 upswing has taken a step back into it's unclear what the cost of money is going to be in this next year and it's also unclear what the appetite is for acquisition of goods and services, you know, 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. And so I think uncertainty is the phrase I would use, though there are certainly opportunities out there.

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