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CEO Insight podcast: Sean O’Shaughnessey, CEO of New Sales Expert, LLC

CEO Insight podcast: Sean O’Shaughnessey, CEO of New Sales Expert, LLC

The following is a transcript of the podcast video above. It has been sparsely edited to increase its readability, but many of the idioms and poor spoken grammar have been left in place. The transcription was automatically generated by and, as capable as that product is, there are times when words are missed, or sentence structure was incorrectly interpreted. We have tried to catch all of these software misses, but we are confident that some still remain. The below text is provided for those that would rather read than watch a video.

Earl Ameen: [00:00:00] This is Earl Ameen, with a 20/20 Foresight podcast, where CEOs of small-to-global companies share their insights. It is six questions in nine minutes because top CEOs know how to listen and be concise. So let’s get to it. First of all, welcome. Tell us who you are and what you do in just a few sentences.

Sean O’Shaughnessey: [00:00:22] My name is Sean O’Shaughnessey. Thank you very much for having me on your program. I am a Fractional Vice President of Sales. My company goes into other companies, and we run the sales department for those other companies. We help them grow, we help them accelerate their revenue, and we help them create a process that makes predictable revenue possible.

Earl Ameen: [00:00:45] Outstanding. Well, tell me, Sean, what’s the best thing about being the CEO of your company?

Sean O’Shaughnessey: [00:00:51] So for me, the best thing about being the CEO is actually not just being a CEO, but actually giving back and allowing myself to help other companies. So, I am in the service industry. As I said, I’m a Fractional VP of sales. I like having the ability to take a company that is struggling to make its revenue targets and help them achieve those revenue targets. I can help them become a prosperous, sales-oriented culture. So, I love doing that for other companies and doing it for multiple companies at the same time.

Earl Ameen: [00:01:22] Nice. Well, I’m sure you’ve heard this as well from other CEOs, just as I have, that leading a team and being able to see the road ahead, to anticipate, can be a challenge. What are your thoughts?

Sean O’Shaughnessey: [00:01:35] I agree that it’s a challenge for many CEOs. I’m a little bit blessed in that I only do one thing. Most CEOs have to run operations. They need a marketing department running for them and sales working for them. They have a lot of different disciplines that funnel to that CEO, and the CEO goes to everything from the head of the company to probably the Chief Bottle Washer.

I am lucky I don’t have that problem. I can actually take part of that problem away from the CEO by running their sales department. So, in this case, the CEO has another CEO, me, running his sales department for him, which is a big benefit to that CEO. So, I do have challenges in running that sales department, but I’ve run sales departments that have measured up to five hundred people strong. So, I really don’t have a problem with a small business that has 15 or 10 salespeople. I don’t have a problem running that kind of organization; I can do that pretty easily.

Earl Ameen: [00:02:35] Got it, outstanding. Well, tell me, what specific piece of insight do you want to share with, and for the benefit of, other CEOs?

Sean O’Shaughnessey: [00:02:46] My advice to other CEOs, small business CEOs, is advice that I gathered from a survey that my company did with 2,300 different participants. We surveyed 2,300 leaders of small businesses, and we came up with some interesting insights:

98% of all small and medium-sized companies do not perform a competitive analysis of their product versus their competition. That’s a problem.

The other big problem that we see is that the marketing spend doesn’t have an associated or tracked ROI. 88% of all companies do not have an ROI that they track and put together in advance on their marketing program.

Those two issues right there make a massive problem that my customers have to get through.

And then, finally, most small businesses don’t have a well-prescribed sales cycle that allows them to say, “When a deal is at this stage, versus that stage, versus another stage, what’s its likelihood of going from one stage to another, to another, and how do we manage that? How do we make sure that works?”

If I can instill that into a CEO, those three things right there can make a difference in the business.

Earl Ameen: [00:04:13] I agree wholeheartedly. Well, tell me, Sean, in your process and journey, what other successful CEOs, your contemporaries, who are successful like yourself, would you like to acknowledge or give a shout-out to and should be on my podcast?

Sean O’Shaughnessey: [00:04:30] (My hero of all CEOs that are active today) There’s Tim Cook out there for Apple, but good luck getting him on your podcast. My true hero. A man I met, admire, and listen to his advice on LinkedIn on a regular basis, is Jim Whitehurst. He is currently the president of IBM, but before that, he was the CEO of Red Hat. IBM purchased Red Hat; they liked him so much that they said, “You know, we’ll bump you up to be president of the company.” Jim is one of the best leaders I have ever met in my life. At one point in his career, he was also the chief operating officer for Delta Airlines.

He is just an amazing individual, and I think everybody should reach out and understand what he’s done. Listen to him on LinkedIn and read his writings.

On a more small basis (small companies), I’m also a big fan of Paul Hinz. He is the CEO of Entando, Inc. Entando is a software company that I’m actually helping. Paul is a wonderful CEO, he’s really good at directing his people, and leading his teams, and he’s going to do a great job as a CEO. Even after Entando, I have a feeling that he’s got a long career ahead of him.

Earl Ameen: [00:05:48] Outstanding. Well, Sean, in the couple of minutes we have left. Final question. How do you celebrate a win?

Sean O’Shaughnessey: [00:05:56] I love that question. That’s a great question.

I actually put this in the book that I wrote. I’m a firm believer in celebrating small wins and individual wins. I’m in sales, so everybody understands we get paid based on commission. We may go on a club trip at the end of the year, depending on the company.

However, I coach all of my salespeople to figure out what is important to them and what small wins they can put on those individual deals that are still significant. If you get a deal that is 10% or 15% of your quota for that year, you should celebrate that with your significant other. I suggest things like picking a restaurant and only going to that restaurant when you’ve closed that big deal. Don’t go there at any other time: no honeymoons, no anniversaries, nothing else, only that time.

Or maybe you’ll buy a new pair of shoes only when you get that new deal.

Or maybe it’s a new handbag or purse.

Maybe it’s a piece of jewelry, but you only buy that when you get that big win.

I’m in Cincinnati, Ohio, it’s really close to bourbon country in Kentucky, so maybe it’s that really good bottle of bourbon that you want to buy and put on your shelf.

Earl Ameen: [00:07:13] Outstanding. Those are good suggestions. So, Sean, it’s been a pleasure having you on today. Last question, how can people find you?

Sean O’Shaughnessey: [00:07:22] It’s easy to find me. You can go to my website, Or you can find me on LinkedIn at Sean O’Shaughnessey. I’m out there on LinkedIn a lot.

My email address is I’ll be happy to reply back and give anybody advice that needs it.

Earl Ameen: [00:07:49] Outstanding. This is Earl Ameen with the 20/20 Foresight Podcast. For more insights, go to LinkedIn and search for the Grey Owl Company.

Sean, thank you very much.

Sean O’Shaughnessey: [00:08:01] Thank you. This has been a great time. I’ve enjoyed it. Thank you.

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