Contessa Gibson


Q: Where did you grow up and where do you live now?
It runs the gamut.  As a youth I lived on the north, west and south side of Chicago. I currently reside on the north side of the city in Old Town.

Q: What university did you graduate from and what degree(s) do you have?
I graduated from the University of Rochester in NY with a B.A. in Music (Clarinet).

Q: You’ve mentioned that you are launching your own business.  What service/product are you offering and who is your target customer?
It’s a tech enabled platform designed to deliver smart matching of customer apparel needs against qualified apparel brands.  My initial target will be the under-served extended sizes market.

Q: What is your job at SmithBucklin?
My role is essentially that of a Virtual Sales Executive. I advocate/drive revenues for my client organizations in their respective industries–a very unique role.  I’m based in Chicago, however I also interface with clients on-site at annual culminating events.

Q: How have you developed your sales skills?
I developed my core sales skillset in a corporate learning environment at a leading IT reseller. Sales acumen is something that naturally sharpens with experience, time, and frequency. I’ve had an opportunity to sell in a number of categories, namely consumer goods, enterprise technology solutions, advertising, conferences/exhibits as well as strategic sponsorships and partnerships.

Q: What were some of the biggest challenges?
Starting out, learning not to take things personally was a big challenge. The ability to objectively separate an issue or problem from the person was a skill that helped me overcome rejections. Leaving your emotions out of the sales cycle simplifies the process. At the end of the day the sale is not about you (the salesperson) but rather solving a problem, or creating a solution for the customer.

Q: How do you continue to improve?
I’m a natural problem solver; however I’m generally attracted to attend professional development conferences, sales & marketing related coursework, and my most frequent weapon: learning via questions. Questions provide a unique opportunity to learn, and also serve as opportunities to make meaningful points, or shed light on unconsidered insights.

Q: What are your  lessons learned?
This list keeps getting longer, but here are some of the major lessons:

    • People like to work with people that they like. Relationships are FIRST. Before anything else, you’re working with people; acknowledging that element before business lays an exceptional foundation for rapport.
    • Don’t take it personally. It’s probably not you, even when you think it’s you.
    • The sale goes to the competitor who managed to communicate the most value to the buyer. It’s rarely just about price.
    • Be great at making your customer shine, it pays dividends, quite literally.
    • Be sincere and have the client’s best interest in mind—they’re smart enough to know the difference.
    • Optimistic sales people sell 33% more. Attitude is everything.

Q: Why did you choose a career in sales?
My personal desire to interact with people supported my move into sales. Prior to sales, I worked in financial services as a statistician for a major credit card company. Schooling and internships in corporate banking, logistics, and a stock brokerage firm set me up for Finance, but my personality and openness to exploring a competitive and objective work environment landed me in sales.  I haven’t left since.

The people and the subsequent relationships I build are very meaningful. When you deal with people as frequently as I do, it becomes easy to nurture the relationships and check-in with them with excitement to learn updates, whether they be personal or professional.

Q: Where did you grow up and how did it shape you as a person?
I grew up primarily on the North Side of Chicago. I think it’s fair to say my diversity of thought, personal experiences, and cultural make-up were impacted by it. Chicago is very defined geographically (ie North, West, South) and it’s fair to say there are cultural assets to each respective area.

Q: Did you begin your career with a clearly defined plan or career path?
My financial services career started relatively defined; however my sales career did not.  It was a risk. With my continued interest in sales, I now have a soft blueprint for growth within my sales career, to ensure I achieve my personal career objectives.

Q: How much, if any, has your career changed you?  And how?
My sales career has enhanced my ability to function as an effective person. Not entirely sure it’s changed me. I think it enhanced and sharpened how I listen and respond to people. Everyone is in sales, but a lucky few realize it. Selling your idea for the buy-in of others doesn’t always need to look like an exchange of money.  It can literally be an exchange for the sake of recognition, or some other intangible capital. My sales career has enhanced my listening skills, my ability to investigate human behavioral prompts (there are a few consistent ones), and it’s toughened my skin. I often joke that I’m a type-A personality with a smile.

Q: If you had a magic clock, would you move time back or speed it forward, and why?
Gosh, I wouldn’t change a thing. There’s sincere beauty in the journey. Everything in my personal and professional life has a purpose, and occurs in divine order. Even when it may seem like a surprise, it’s designed to prepare or teach me something. Right now, I welcome the journey that every day delivers.

Q: Please describe the non-profit and/or Diversity & Inclusions initiatives/organizations you support and why?
United Way for their wide-reaching impact across the Chicagoland area and abroad, and Junior League for their focus on women and children empowerment.

Q: You dedicate a significant amount of your time to non-profit initiatives.  Why?
In an effort to avoid sounding cliché, I feel obligated to give back. There were a number of people, programs, and care that supported my personal and professional successes. It is so very necessary that I give my time, resources and time to help where I can. Women initiatives that support empowerment, self-esteem alongside Music Education outreach for youth are two areas that will always be incredibly meaningful to me. Exposure to positive, empowered women as a youth has paid invaluable dividends that words cannot communicate. Exposure to music enabled my training as a classical clarinetist of 16+ years. Music strongly supported my discipline, competitive nature, and a conscious appreciation for culture, the arts, and their sustainability.

Complete the following sentences…

Just when you think…you’ve become familiar with all of the possibilities, you haven’t—and that’s a great thing.

Looking back now…I have a heightened sense of nostalgia for the opportunities afforded to me through hard work, sacrifice and care of my loved ones.

Whenever…things seem “bad” I remember that there is no such thing, and it could always be worse! The upside is often the only side worth thinking about 100% of the time.

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4 replies

  1. Thanks, Sherry — and thanks to you as well, Contesssa. The Consulting Industry opened my eyes to the power and possibility of sales, so it is always a pleasure to hear tale of an earnest practitioner.

    And as a Gibson, too, it is always interesting to hear stories and histories of other fellow travelers. I spent about six years in Chicago, but my family roots go back through Kansas, Oklahoma and Texas.


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