Secrets of Sales Success for Bootstrapping CEOs

Being CEO of a company takes two talents: excellent leadership skills and the ability to attract and hire people smarter than you. Ok, so maybe it takes a few more skills than that, but without these two, you are dead in the water.

As Executive Visionary Vixen, my daily goals are: (1) attract new business (2) continued deepening of current client relationships, so that they continue to respond to calls and communications (a reflection of their loyalty to our team) (3) keep the RTL team focused on achieving our goals.

Why are these my goals as CEO? If our team continues to do what they do best — and they always do – like producing content, implementing social media marketing plans, content strategy development, then I can do what I do best…check in with our clients on a regular basis and call on new prospects.

In my heart of hearts, I love the sales part of my job. So I suppose, in my case, I’d add one more skill to a bootstrapping CEO’s basic toolbox – exemplary sales person. My mother, the consummate saleswoman, passed her gift of gab on to me. That personality trait, aligned with her ability to sell stink to a farmer, made her an amazing salesperson. Yes, I inherited that ability also, but I use it responsibly. I would never sell clients anything I truly didn’t believe they needed in order to achieve their goals.

Needless to say, I get giddy when I start making cold calls. I jokingly call it dialing for dollars, but that’s not really what it is. We don’t take on just any client at RTL, only those who truly understand the value of what we do make the final cut. Dialing for dollars, in the literal sense, only gets you the closing meeting. Beyond that, you must have your “A Game” in place to close your “A Prospect”.

Sales Success Tips for CEOs

(1) Identify prospects with a connection. Perhaps you love the products of a certain business. Maybe you went to college with the business owner, or perhaps the business is a non-profit whose cause interests you personally. If you have a true passion for a potential client’s business, the decision-maker will see it in your eyes and hear it in your voice when you present your proposal. This makes it much easier to show them the value of what you have to offer.

Allow me to share a real live example with you. About 4 months ago I started prospecting a venture capital firm about a portfolio company they invested in that had potential to impact the organ donation community (I had a liver transplant 21 years ago).

Not only did I successfully help them understand our team’s expert ability to build public awareness for their brand and message, RTL executive staff and I demonstrated our collective knowledge of the industry. Apparently, we did such a stellar job of it, they signed us on to handle content development, social media marketing, and public relations for the entire parent company. I love it when clients up-sell themselves. Who wouldn’t?

(2) Don’t take yourself too seriously. Yes, you need to put forth a professional demeanor, but spend some time connecting on a personal level with your prospects too, and laugh A LOT! One of our recent new clients is a baby consignment store in Atlanta and the owner is single female approaching the birth of her 2nd child. We spent the first 7-8 minutes of our meeting swapping kid stories and got to giggling so hard we were crying. As two single women, we connected by talking about one of the greatest roles a woman can have – motherhood — and how to do that as a single mom. Priceless connection.

(3) Observe the obvious and adjust accordingly. If you walk into a storefront meeting looking sharp and polished with makeup perfectly applied (like you always should) and your prospect looks like a slob with greasy hair and rumpled clothes, then accept the fact that you probably won’t close the deal. What’s more, even if you could close it, you probably shouldn’t. Why? The relationship will not prove satisfying for you or the business owner.

Think about it. No successful entrepreneur will interact with the public (e.g. customers, vendors, digital marketing experts) without at least looking well groomed. Don’t waste your time on this kind of prospect. Do a quick presentation and get out. Chalk it up to experience.

(4) Present yourself with authority, but recognize that you don’t know everything. After all, that’s why RTL has such an experienced, diversified team in place. Together, we know a heck of a lot more than we do as individuals. When asked the question you don’t know how to answer, say something like, “Heck, I have no idea. But you know what? Samantha, our Executive Raconteur Extraordinaire, knows way more than me about this. I’m sure she knows…let me call her. Is that ok?”

A great business owner will surround themselves with a smart executive and support team. The fact that you admitted you don’t know, but have a person on hand that does, will build trust between you and the prospect.

(5) Stay accessible to clients and make their goals your own. Clients need to know that you care about their business, their goals, and their lives. Stop in to grab a smoothie in their store, remember birthdays and anniversaries, listen to them as they mull over a business decision. Take the time to truly care about each client. This genuine interest will not only enrich your life, but will deepen your business relationship.

Your turn: How do you handle executive responsibilities of your small business? Share your tips and stories with us.


Smart Ideas. For Free.

Rectangle 78

Lorem Ipsum

Lorem ipsum dolor sit amet, consectetur adipiscing elit, sed do eiusmod tempor incididunt ut labore et dolore magna aliqua. Ut enim ad minim veniam, quis nostrud exercitation ullamco laboris nisi ut aliquip ex ea commodo consequat. Duis aute irure dolor in reprehenderit in voluptate velit esse cillum dolore eu fugiat nulla pariatur. Excepteur sint occaecat cupidatat non proident, sunt in culpa qui officia deserunt mollit anim id est laborum.
Rectangle 78


We appreciate the time and thought you put in to sending us this message. RTL Digital Media is grateful for every opportunity to interact with people like you.

This is (obviously) an automated response to acknowledge receipt of your message. If you asked to be added to one of our distribution lists, consider it done.

If you asked for more, then we’ll be back to you promptly with a personalized reply that addresses your request.

Again, thank you for reaching out.  

Junior SEO Specialist

Ann Jennith Fernandez

Junior SEO Specialist

Putting The Extra In Extraordinary Visibility.

Ann began her professional career as a customer service representative. After outgrowing that position, she worked as a Virtual Assistant for a logistics and real estate company. Her keen interest in technology and natural ability to apprehend technological concepts and systems brought her to the RTL team. Ann’s work ethic and firm knowledge of SEO are greatly appreciated.

When she’s not working her SEO magic for our clients, she enjoys watching movies, reading great books, and spending time with family and friends.

Ann holds a Bachelor of Science in Information Systems.