Transforming Obstacles into Opportunities

The pandemic has changed the way we navigate everything in our daily lives, from working to parenting to connecting with our loved ones. In addition to requiring resilience and patience, 2020 has also given us opportunities to be creative. Sometimes when we least expect it, moments of significant change and upheaval can create occasions to try new things that lead to great success. With that in mind, I’d like to share Whitney Henry’s story with you. She is a Trailblazer who took a professional leap of faith that paid off.

Whitney Henry is an Associate Solution Engineer at Salesforce, but tech sales is Whitney’s second career. Majoring in Recreation and Leisure Studies with a concentration in Sport Management at Howard University, Whitney began her career in professional sports sales. After graduation, Whitney’s work focused on creating ways to engage fans in large groups and drive ticket sales for professional sport teams. She was in the business of entertainment and she enjoyed the games, the competitive environment, and the opportunities the professional sports industry provided.

However, after ten years her career and salary became stagnant. “I had gotten to a point where I wasn’t growing in my career, so I decided it was time for a change.” Whitney shifted her focus to the tech industry. After some research, she moved from Florida to Colorado because her research indicated that Denver was quickly developing a reputation as a city with an up-and-coming tech scene.

Moving from Sports and Entertainment Group Sales to Tech Sales

When Whitney arrived in Colorado, she began working as a Sales Development Representative (SDR) for a popular reservation management platform as a way to diversify her skillset. This new position was a hybrid mix of Sales Development and Business Development. While working in this role, Whitney learned that Salesforce was coming to Denver. “As an advocate of Salesforce’s CRM tools from my time in sports sales, I was intrigued [that Salesforce was opening an office in Denver] and when I saw that Salesforce was hiring, I knew I had to apply. I started by doing research into other sales careers, and I kept coming across tech. Salesforce seemed like it would be a great company to work for.”

Q&A with Whitney: Making the Shift to Tech Sales

After learning about her career trajectory, I asked Whitney to tell me more about her shift into SaaS sales and what advice she would have for other saleswomen looking to do the same.

Cherilynn: Once you decided to make a career shift, how did you decide that tech was the right place for you?

Whitney: I thought tech would be a new challenge for me. It’s a growing industry, but it’s also fruitful – with all the investment that comes into tech, I knew there would be more growth opportunities for me. In tech there’s a delineated career path that I didn’t have previously. When I was in sales in the sports industry, I had no idea what would be next for me. I didn’t know if I would ever get promoted. In tech you’re given your outline or your requirements, or you know what’s expected from you. You know if you meet your goals, then you’ll be rewarded. If it doesn’t work out the way you planned, there’s another way for you. One of the things I value is that at Salesforce there is a clear career path to reaching the next step in your career.

Cherilynn: What would you say to someone who’s thinking about making a career shift into tech sales?

Whitney: I would recommend that anybody interested in getting into tech should make a serious effort to do so. If you want to do it, then you should be here. I have done the work and deserve to be at Salesforce. Don’t give up. Some of my former sports sales colleagues really want to get out of what they’re doing, but they’re scared, or they feel like they don’t have the skills. I tell them to just go for it. I had to start over, but it was worth it. I know that there’s a lot more for me to [accomplish before] there’s finally light at the end of the tunnel. Just keep going. Starting over is difficult, but it can bring large rewards.

I think being a salesperson, although challenging at times, is rewarding, not just professionally, but personally. I feel like I can talk to anybody, at any time, about anything. Working in sales has developed my confidence, improved my communication skills, and taught me how to negotiate. Because sales can be a challenging career path, it’s important to work for a company that provides growth opportunities. Salesforce has not only prepared me to succeed in my current role but has also prepared me to take on future opportunities as well.

Cherilynn: What’s the best career advice you’ve received?

Whitney: Trust the process. When I heard that in the past, I never really understood it, but when I started at Salesforce as an SDR there was definitely a learning curve. It was challenging at first, but I trusted the process. I took things step by step, started improving, and I saw the fruits of the process. Trusting the process is just staying patient, doing what you’re supposed to do, and waiting to see the results.

As an experienced SDR, Whitney was strategic in her approach to her career development and took advantage of one of the many Salesforce career paths. Through networking and leveraging her product knowledge and strong sales foundation, Whitney was able to pivot to a new sales role. By taking advantage of the career development opportunities available to her at Salesforce and putting her previous experience to good use, Whitney was able to take the next step in her professional career by starting a new role as an Associate Solution Engineer in the Essentials Small Business Unit in October 2020.

Cherilynn: What’s it like to be part of Salesforce’s new Denver team?

Whitney: One of the driving forces that interested me in Salesforce is that the company values Equality. I had this rare opportunity to be a part of opening a Salesforce hub in Denver and to be one of the first people in the office. We have twelve Equality groups. I’ve been able to start BOLDforce (Black Organization for Leadership and Development group) in Denver, and we participated in the Martin Luther King, Jr., parade that I was able to help coordinate. We’ve also done some volunteer events in the Denver community. I was able to represent the Denver hub in San Francisco at Representation Matters, Salesforce’s annual Racial Equality Summit which elevates luminary Black, Latinx, and Indigenous talent who are leaders in their fields and are standing up for Racial Equality.

Although I’m one of only a few people of color in our office at the moment, I know my voice matters and I’m able to share my ideas for building a more inclusive workplace. Over the last year, Salesforce established a Racial Equality and Justice task force that is committed to driving change. As a woman of color, this makes me feel seen and valued and that my voice matters.

As the businesses begin to reopen, it’s important to tap into what inspires you to keep moving forward. For me, one of those things is the time I get to spend connecting with other professionals navigating careers in sales as a woman of color. Read about my conversation with Seanté Baker. I hope her story will inspire you to continue building your network and breaking new ground as a trailblazing woman in sales.


Chief Learning Officer, SIS

Cherilynn Castleman, Sales Trainer/Executive Coach, has been a sales executive for 20+ years. With her natural talent for teaching and a drive to sell, Cherilynn uses her skills to coach and train other executives and sales professionals.

Sistas in Sales, LLC (SIS) is a community for women of color sales professionals to network, advance their careers and most importantly, find sisterhood – offering events, thriving Slack community with companies hiring now, and career coaching services. Learn more about Sistas In Sales membership here, connect with us on  LinkedIn, InstagramFacebook, and Twitter.

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