Help Me Choose
Jordan Benjamin

By: Jordan Benjamin on June 2nd, 2021

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Sistas In Sales, Creating Community for Women of Color in Sales


JB: How’d you get into sales?


Sales wasn’t something I went to school for

Black people in general, women of color are not involved in the tech sales industries as much as we’d like them to be. However black women are the fastest growing group of entrepreneurs. 

Not a lack of business sense/acumen. It came from a lack of awareness and opportunity meeting them where they are at. 

Caribbean family, they are adventurous, came to America looking for adventure and opportunity. That is one of the biggest things in business & sales is being confident taking a step outside yourself, taking a risk in your decisions.  I was raised in that structure. That’s how I navigated through life, that’s how I saw America and opportunities ahead of me. But that’s not everyone’s view and opinion of America or where they are. It goes to show how important mindset is. 

I was raised to believe opportunity existed for me anywhere I go no matter what I do. I operate with a sense of positivity. 

I thought I wanted to be a lawyer, that didn't work, maybe drama. That didn’t work out. Hopped on Craigslist in 2013 and saw an ad for Yelp. 

The mindset piece, there are ads for jobs everywhere, but if you aren’t operating with a sense of utility. I applied on a whim, just looking for something that I could manage while I was still trying to figure out what I was still really passionate about, then I got the job. 

Got the job, had a one foot in, one foot out mentality. I wasn’t sure if it was for me or not. But once I got on the phone, something clicked and I was able to gamify it and make it fun.  I wasn’t totally connected to it, but it was just another version of me, and didn't see it as my natural progression to being an AE/Leader/VP. 

Through that work I realized I could gamify this and am actually good at this, that realization that I am GREAT at this. 

Most of us that come into sales from a non-traditional background, may take a little longer to get to that AHA! Moment. If they aren’t feeling supported by their team or community, somebody that could be a fantastic salesperson may not get to that place. I was lucky to be in a sandbox that allowed me to learn and help me get there. 

JB: Our upbringing has such an impact on our mindset, how we approach our lives and what we do. Seeing your parents leave their family and their home is such a big risk to take, seeing that type of mentality and mindset is fascinating. 

Talk to me about community and how you are building DI&B to the companies you work with and building Sistas in Sales as well as building belonging in the companies they are part of.



At Yelp! I was growing and realized I was one of the only Black sales leaders and was my own pioneer.

I grew up in a Caribbean community, living a few blocks from my childhood home in the Bronx. 

As I moved through the ranks I was less and less connected to what I knew. 

It was scary for a few reasons being outside of your community. You don’t have experience connecting with people. We like to be around folks that make us comfortable. It’s hard when you’re in a space where you aren’t sure if you’re an enemy or a friend as a black person

I was inspired to step out of my comfort zone and realize Oh i’m alone now and nobody is in charge which helped inspire me to start thinking about SIS.


JB: Humans are tribal, that is our root and through Covid so many people are individualized and on their own that takes away our power to be better people that allows us to achieve more as a group. As we talk about getting through that fear initial as you talk to women, especially Black women.  What are you hearing as some of those moments that have helped them get over that initial hurdle to go into something less familiar?


It all came down to being in the same space

I started SIS at a dinner party and found women I knew that were committed to sales so I knew that group would have to be committed to sales

Most people don’t get to that stage because it takes awhile to move through the BDR/SDR role to further their sales career

I found 10 people, but didn’t know most of them and +1’s

I wanted them to know I took it seriously and we put together this beautiful EVENT, with floating candles, beautiful spread, catering, fresh flowers and so much more. 

I didn’t ask all the questions I wanted to until the last 15 minutes because all they wanted to do was connect with each other, open up conversations, create a group chat, take pictures and connect! It was amazing and validated my career!

It was magical and an amazing experience for people representative of Tech, non-profit sales, fashion industry. 

People didn’t realize their skills are applicable to other industries because you may not think that you have anything to share. 

That feeling of opportunity was the magic in the room! People connecting and they turned into a focus group and is how SIS was born!


JB: Tell us about SIS and what you’re doing now as a community!


We had 10 members, Salesforce gave us some space, somehow had 50 people showing up and now up to 3,000 members and now Hannah is our head of Europe in the UK!

In the early days of a company you know where your customers are coming from; they’re your family and friends.

Now it’s hard to know how people are finding us.That’s why I ask how you found out about us!

Through talking and evangelizing, more and more women are flocking here!

JB: What do you guys do? What has surprised you about this community?


We were event based strictly to start, but now are making sure all black and brown women can be successful and find mentored by veterans in the space from people with leadership in the community. 

It was really tough to rattle off 4-5 Black women at the exec level in sales at the time that was my measure of success. It’s through events who had never been tapped to talk that are now bringing that awareness in the community and we can rattle off 40-50! 

All online events last year, 1500 attendees at our summit going for 3,000 this year and 30 countries

Now investing in the members sales growth. Chief Learning officer who does sales coaching with these women and then some additional big announcements. 

Job boards in beta coming out soon for companies who want to partner and can post their job boards. Looking to grow their operations to support their community as it grows. A business as its 4th year starting to make major investments in our operations.

Team meeting with team of 6- a community turned company now have to be this way now and couldn’t do it without their sponsors. It’s a self-feeding system that they’re in. We grow as fast as we can get resources to grow and are so thankful for our sponsors. 

JB: Recording in Mental Health Awareness month in May. Talk to us about the Therapy Post as you mention it’s been a game changer for you.  Therapy has been such a powerful thing for me even as I took some time off because therapy is a powerful vehicle for awareness and change.  You’re running your Mental health challenge. Talk to us about how Therapy has impacted you. 


I am a planner and you just start to accept who you are. 

As my dad got sicker and sicker I was having anticipatory grief. I don’t think people should wait for a really bad experience to find therapy. It was so powerful for me, I am trying to create a group therapy in our 90 Day Challenge.

Many black people are “just happy to be here” which I want to challenge and have people approach their career with a little more direction and change their mindset.  

It’s much more mental than physical, getting through the imposter syndrome mindset and being more in the present. Having a therapist that may help you get comfortable having a conversation with your manager about a pay raise, a promotion and not just being OK to be there. Understanding your relationship with money, how you spend your money, bonuses and commissions.

  1. Sales career
  2. Personal finance, what is our relationship with money?
  3. Wellness
  4. Motherhood - Many black women are the matriarch of the family
  5. Relationships

Meet every 2 weeks on these topics then come together with a summit and discuss as a group.

JB: Many people wait for something terrible to happen before they will approach therapy.  It’s looked at as a last resort, I’m broken which is so far from the truth as to how you can understand yourself and be prepared for the bad stuff that does happen when we fall on our face. 

How do you bounce back from the tough months?

CG: Therapy has helped me have a lot more self-awareness. 

Sales for me when I started selling I didn’t realize how formulaic it was.  If I didn't close something it was one of hte many different variables, in actuality there was something I could’ve done better but I needed to identify my patterns like not prospecting enough in 

My resilience came from experience and came from being honest with myself it’s not something I need to be attached to or take personally. And that takes a lot of the emotional strain off of you, the negative self-talk isn’t necessary. 

Write down the actions that you did and look for what was missing and go from there. 

JB: Love winning or hate losing?



I love WINNING more. I don’t think about losses as hatred, it’s more of a learning moment. I enjoy looking at my losses with a scavenger hunt mentality.  What did I do here? It’s actually pretty cool to me, you have that voice in your head that helps you sense when things are off track. It’s not really a loss, it's a predictable outcome based upon how you go about your sales motion.  I like a win, especially a predictable win, which helps me feel even more control of how I am going to operate.  I know how this goes, I’ve seen this song before. 

JB: Top qualities in leaders that you look up to, respect and try to emulate?


I love leaders that are curious about the industry that they serve

Yes sales oriented but you realize we are selling CONCEPTS and to sell that you have to be educated in the industry, know your competitive space

Be as curious as risky as it was for your CEO to build the company to begin with

This is the concept I want you to be bought into - i’m not talking about the features then I can bring that level of enthusiasm to the customer

I like a manager that has sales strategies but it’s the excitement we bring to the customer that will break these walls down

JB: What does success mean to you?


For right now,  getting my footing here, as 1st gen American, I’m still figuring out what that means to me. I’m motivated to create financial success for myself. We’re all somewhat motivated by that in sales.  It’s something that anchors me, makes me feel comfortable and safe.  I’m building enough family here and making enough business decisions to help me feel buoyant. 


JB: How can we build diversity in sales and be a champion. 

CG: You're going to have to put in work to get people to see the value of being in sales and to join on the rocket ship that you’re on. 

The language of business being in your household.

I had the language of opportunity, but there are some people that had the language of business, sales is not a foreign concept for many families, but it is for many black and brown communities. I couldn't point to a mom who is an ex-Salesforce VP or leader, now I can.


JB: Where can people find you?



Sistas In Sales

Virtual Sales Summit

About Jordan Benjamin

Jordan is the founder of My Core OS. After spending years in sales, working with sellers and studying peak performance he found an opportunity to help sellers level up to not only build peak performance at work, but to also create harmony between work and life so you can sustain performance over the long term.