Meet CoachRichardGPT, your 24/7 Sales Trainer and Coach

Women in Sales – The XX Factor with Gabrielle Smith


After cutting her teeth in business development, Gabrielle Smith took her skill set to the sales arena, and generated significant profits for companies like Cloud Sherpas and Amazon Web Services. Now she’s an executive sales strategy consultant working with both start-ups and enterprises to drive market growth.

Needless to say, we were eager to speak to someone with such a rich and varied sales background. Luckily, Smith was more than happy to share her story.

Q: How many years have you been in sales?

A: I have been working in sales for the past 15 years.  During this time I have been both an individual contributor and sales leader.

Q: Can you please describe the “aha” moment when you decided you wanted to be in sales?

A: I’m not sure that I had an “aha” moment. I decided to go into sales after my college career choice (social worker) was a disaster. I knew within my first month of selling that I loved it. Meeting new people, a new challenge every day, and getting to do some incredible things that you don’t get to do in other roles. Sales is the only job where every day is different.

It was also a realization that grew as I got to know more and more of my customers. In my 15 years of selling software and services, I have met some wonderful people and have maintained fantastic relationships with them. I am still friends with many of my early customers and to this day, when they have questions on a particular product or software they call me (even though I have not worked with them for years).

And then there’s the fact that I’m a competitive person by nature. I played sports for most of my life until college. Sales to me gave me that same excitement and that same feeling of the win. I quickly realized that the harder I worked, the more successful I was at what I was doing. My customers benefitted from my efforts and I was greatly rewarded. I can recall so many great experiences of late nights working for that win and how gratifying it was to get. One of my first customers took me 14 months and countless meetings to get the deal. Everyone, including my manager, told me it was a lost cause, but finally after many, many hours of work, I was standing in that same manager’s office with signed contracts. (I subsequently hung a copy in his office with the words “persistence pays off” written on it.)

Q: What can you tell us about the single biggest sale you ever closed ($, sales cycle, company/ industry, etc.)

A: The biggest sale I ever closed had to be selling a Microsoft contract to a multinational computer technology company. At the time, the company had just acquired another company and was owned partially by a competitor. They were almost completely an IBM Lotus shop and I had the daunting task of selling them an MS contract, which included MS Exchange for email.

The sale was big in many ways outside of the sheer dollar value of the contract. The sales cycle had complexity from a political standpoint, and public standpoint, and deal structure. It took 13 months to close, and during the course of it we “lost” the deal about three times … once because of another MS team! After many, many revisions and stops/starts, the deal closed for multi-million dollars annually.

I think at the end of the day, taking the approach to understand what the client needed and the internal challenges they had to overcome helped us to structure a plan that worked for everyone. It was also a willingness to drive to a common goal by BOTH sides that ultimately caused this relationship to work. I spent countless hours with the point person at the customer and we got to know each other very well. The honest communication and degree of trust for one another we were able to develop helped us both create a scenario that met everyone’s needs.

Q: Which women in sales do you admire most?

I would have to say two of my former managers at Microsoft, Ali and Sarah. Ali was the one who gave me my “sales words to live by” and I still use it today. Ali taught me to “be bright, be brief, be gone” which boiled down to being respectful of people’s time and delivering an intelligent, succinct message. I train every one of my sales people with this phrase. The concept of having respect for someone’s time and making your message meaningful and smart goes so far, and so few people follow that principle.

Sarah was my direct manager and was the epitome of what I would aspire to be as a saleswoman in tech. Sarah presents as a very attractive and stylish woman and has a masters in engineering – a combination that, at the time, was not often seen. Sarah always stayed true to who she was and earned respect through her actions and her intelligence.  She taught me to sit back and use my brains to basically get a customer to sell themselves (a tactic she also unfortunately employed on her team when needing us to do things we didn’t want to do). Not only was Sarah brilliant, she was also a dedicated mother of two little girls. I had been told so many times in my younger years that I needed to choose between a successful career or family.  Sarah was the shining example that gave me the confidence to know that I could, in fact, have it all!

Q: If you could go back and give your early career minded self advice about a career in sales, what would that be?

A: Have more confidence in your abilities, and it’s okay to walk away. I see it time and time again in sales people and I was told it early on as well … sometimes you are better off walking away from a sale than fighting for something that will ultimately cost you. Many times early on I would chase down customers, or not share with the customers how wrong I thought they were, just to try and get a sale. I know now … it is sometimes better to lose the battle but win the war.

Q: What advantages do you think women have in sales over men?

A: I think women are perceived to be more trustworthy and less threatening in many scenarios, which allows them to gain more insights during the sales cycle. It’s often easier for a female sales person to get an initial meeting as well, at least in technology, as there are fewer women in the field.  We will tend to stand out more.

Q: What advice would you give to men about working with women in sales?

Don’t be condescending and promote your female counterparts for the work they do. We may be a pretty face, but that is not what closes the deal! Often times we can sell as well, if not better, than our male counterparts. Women are also less likely to promote themselves in the same manner as their male counterparts.  Encourage them to do this more often if given the opportunity.

Thanks for sharing your story Gabrielle!

Let us know what you think of Gabrielle’s story, and click here to subscribe to “Women In Sales – The XX Factor” series.

Other Women In Sales Interviews:

Social Stuff:

Follow us on Twitter: @rharris415

Follow Gabrielle on Twitter: @cloudgirl1000

Got some feedback? Care to share? Go for it! Comment! Share!

Leave a Reply