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Black in Tech: Jessica Wilson, Revenue Enablement Manager at LeanIX

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Our Black in Tech series features the career path & advice from Black professionals in the tech industry. In this Q&A, Jessica Wilson, Revenue Enablement Manager at LeanIX shares her story.

Jessica Wilson LeanIXWhere did you grow up and what were you like as a child? What did your parents do for work? 

I am from Minneapolis, MN. I was a shy kid, good student, and active in school sports. I played softball and basketball all the way through college. I worked at various places since I was fifteen such as at the local YMCA, Target, Sonic, and so on through college. My mother works in the insurance industry and my stepfather works at a furniture company. They were amazing parents who sacrificed much to provide opportunities for my brother and myself.

Where did you go to college? What did you study and what did you do after graduating? 

I graduated from St. Olaf College in MN. I double-majored in Exercise Science and Spanish. I didn’t pursue my majors post-college. I ended up working in sales for the first two years after college, trying to figure out what career I truly wanted.

What inspired you to get into the tech industry?

After college, I was a bit lost about my career and decided to move out East to figure out what I wanted. I started out as a Verizon sales rep. This job provided my first opportunity to explore sales training and I knew I wanted to continue on that track.

Fortunately, the east coast is a hub for technology. After my sales/training role with Verizon, I took a job at LogMeIn, Inc. I had to work from the ground up and learn about an industry I knew little about. They had an amazing onboarding program that taught a range of skills in customer service and technology. I learned I had a knack for IT and had found the perfect industry for me.  

Jessica Wilson LeanIXWhat has your career path looked like in tech and the various positions you’ve held before joining LeanIX? 

The best way I can summarize my career path in tech: there wasn’t one. There was no direct guidance on how to pursue Sales Enablement and rise through the ranks in tech companies.

If anything, I had to create opportunities for myself through self-education, collaborating with peers, being my own advocate, and learning to say no to responsibilities that wouldn’t help me move forward. When I started selling Verizon, I worked up the nerve to share with my manager that I would like to practice public speaking and training. He generously gave me a platform to teach the sales skills I had mastered to others.  

At LogMeIn, I started in level 1 tech support and customer service. After a year, I vocalized to my manager that I would like to participate in their mentorship program, help train my peers, and shadow their Learning and Development organization. All the while, I still had to fulfill my job’s responsibilities. It was all worth it.

My breakthrough came with NetBrain Technologies as an entry-level Sales Enablement Specialist. Every prior opportunity that I chased helped prepare me for the interview with a company that targeted network automation. I had to demonstrate an ability to learn and articulate tech concepts in a concise, meaningful way to sales and engineers. I reported to the VP of Sales Enablement and her mentorship was invaluable. She taught me how to value my business worth, never apologize for my success, and negotiate to achieve new career heights.

Next, the next opportunities I took at Benefitfocus and Syniverse stayed in the sphere of Sales Enablement and technology. My career was shook, as were many others, with the impact of Covid-19. I, fortunately, found LeanIX, Inc. where I reached a milestone of achieving a manager title. Of course, there is still much to achieve career-wise and LeanIX has proven to be a great place to continue my professional development.

Can you share the high-level responsibilities of your current position as Revenue Enablement Manager at LeanIX?

I am currently on a team of four and report to the Head of Revenue Enablement. I am responsible for the learning and development for all global customer-facing teams which include sales, technology, and product skills. Customer-facing teams apply to leadership, pre-sales, and post-sales. Although I have a focus on the US, I collaborate with the rest of the team to achieve global support. It’s a great job because I am able to build relationships with the team members and be part of their professional development. I often act as a facilitator between leadership and sales to help drive new concepts, processes, and skills.

What has attributed to your success thus far and what types of obstacles have you had to overcome along the way as a Black professional? 

Being a Black woman in a predominantly White industry can often feel like there is a magnifying glass hovering over your head. You are painfully conscious that you stand out and that others are watching you carefully. They clearly are trying to ascertain will you be like them or will you be something else? The pressure to represent has been a heavyweight always at the back of my mind. The problem was that I often didn’t even know what “to represent” truly entailed. All I knew for certain, was that White people held positions of power and leadership.

Early in my career, I often under-valued myself in interviews and business opportunities because I thought I was just lucky to have whatever they gave me. I thought success would come if I mirrored everyone else. I adjusted my language, cultural references, and listened more than I spoke. I tried to fit into the box that would make the person across from me as comfortable as possible. The sad truth is that this made me forgettable. It was enough to keep my job, maybe I received praise here and there, but my career progression was clearly stunted.

Finally, I realized I had buried pieces of myself that differentiated me from my peers. A beautiful aspect of “African-American” culture is how we nurture and encourage traits such as emotional intelligence. When we ask you how you are, we want to know the breadth and depth of it. It isn’t just a pleasantry. It is never an inconvenience. Once I embraced this and intertwined it with my work, it changed the way people connected and partnered with me. I built bridges across departments based on human connection and, in turn, their stories and willingness to collaborate helped me succeed.​

Jessica Wilson LeanIX

What types of programs and initiatives does LeanIX have that support diversity, equity, and inclusion?

LeanIX is supporting diversity, equity, and inclusion in many ways. For example, LeanIX has a volunteer DEI committee that brought in third-party evaluators to help identify inclusion gaps within the company. Additionally, Leadership offers our All-Hands meetings as a platform to promote findings, acknowledge areas of improvement, and solicit employee feedback. There is a “Ladies of LeanIX” group as well which provides another channel for women to collaborate. I appreciate that LeanIX also honored Juneteenth before it was officially a federal holiday. There are still huge strides that need to be made, but the effort thus far is appreciated.

What advice would you give to other Black professionals who are interested in joining the tech industry? 

It is clear that black leaders and board members are scarce in the tech industry. That being said, I want my black colleagues to understand that our insights, culture, language, experiences, and drive are needed now! There are more opportunities than ever for you to take your place in this exciting industry. Technology breaks borders and companies are global citizens. In order to service a global customer base and range of cultures, companies need diversified insights to survive. When you interview, don’t sell yourself short by reducing who you are. Breaking the mold can equate to millions for a company’s future prospects.

While general awareness of the problem of diversity in the tech industry is a step forward, to make a lasting change, real actions need to be taken.  Do you have any ideas or suggestions on what companies or employees can do to step up and make a difference?

First, there is a significant disparity that starts with the leaders hired into a company. You will find many black employees in individual contributor roles such as customer service, engineering, professional services, and more. Unfortunately, they are often overlooked when leadership positions are offered.

As a solution, implement mentorship programs to help nurture future leaders from within. Teach interviewing and leadership skills to everyone at all levels. Promoting leaders from within saves thousands in recruiting costs and increases time to value because they already know your business.

Second, expand the recruiting net to more regions. With remote work proven to be sustainable and productive, there is no need to limit recruitment locally to a physical office. You will inherently open the door to more ethnic and gender diversity, and new sources for innovation.

About the

LeanIX offers Software-as-a-Service (SaaS) for managing Enterprise Architecture and multi-cloud environments to enable organizations to take faster, data-driven decisions in their IT.

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