This Trailblazer Shares 5 Rules for Transforming Obstacles into Opportunities

In 2016, she found her voice. Three years later, she used it to find her calling.

Amy Cook
AppExchange and the Salesforce Ecosystem
6 min readAug 31, 2020

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For Jenifer Robertson, a Salesforce architect with T-Mobile, the journey from being a military spouse, entering parenthood, pursuing a career in technology, earning an MBA, and ultimately going forward as a single parent hasn’t been easy. But the practice of transforming obstacles into opportunities has been instrumental in realizing her proudest achievements both personally and professionally.

As women, so much of what we do relies on instincts. But as I talked with Jenifer about the decisions she’s made, I learned that she attributes her success to five rules that have consistently helped shape her life strategies going forward. And she hopes they can help others move forward too.

Jenifer Robertson, Salesforce Architect at T-Mobile.

1. Don’t question your worth.

We’ve all experienced times in our lives when we didn’t feel we could expect more from other people. But that self-defeating behavior simply won’t get you closer to your goals. Whether it’s needing more support in a relationship or expecting fairness in the workplace, never question your worth.

“Because I decided to go into a field that is predominantly male, I am constantly confronted with the gender gap reality that exists with women in the technology field,” Jenifer said. “On a team of 53, I’m one of only four women. But as more women pursue careers in STEM specialties, I hope to see that change.”

In a recent survey, more than two out of three tech professionals say they’ve noticed more women in the industry compared to a few years ago. And some employers have implemented recruiting programs to increase diversity and cultural programs to support women and other minorities. Jenifer believes that the tech industry has a long way to go. But as more companies welcome diversity and open up key leadership positions for women in the tech industry, she hopes women will prove they can bring a lot to the proverbial (and virtual) table.

“On a team of 53, I’m one of only four women. But as more women pursue careers in STEM specialties, I hope to see that change.”

2. Network. Network. Network.

“Don’t be afraid to put yourself out there,” said Jenifer. “When you’re networking, you’re not only building professional relationships, but it’s an important part of job growth.” As you meet new people and listen to their stories, you will discover new ways to better navigate and expand your own career path.

“Success in a career is largely attributed to the pool of information or ideas you have garnered over the past. When networks have been created, it fosters a trade of ideas to sustain long-term relationships and mutual trust,” explained Forbes contributor Bianca Miller Cole. “When you are receiving ideas, it helps both in your place of work and out, in addition to instilling best practices that soothe your career.” Always take the opportunity to put yourself out there. It’s through meeting new people that we can visualize and learn our next professional move.

Jenifer (second from left) with fellow T-Mobile employees and former CEO John Legere (2019).

3. Embrace challenge.

As tempting as it feels to remain in a safe, comfortable place of knowledge in your job, don’t be complacent. New opportunities only appear when we push ourselves to find new ways to grow and expand.

A wise person once said, “If you’re coasting, you’re either losing momentum or else you’re headed downhill.” And that has definitely been both Jenifer’s and my experience.

“When I decided to re-enter the workforce, I started as an admin at T-Mobile,” said Jenifer. “After seven months, I was promoted to oversee B2B accounts. Then, I was recruited to Product and Technology as a solution architect to oversee B2B Salesforce Instance. Along with those duties, I served on the board of a military nonprofit.”

The point is, each step in a worthwhile career requires learning new things and putting new abilities to the test. But Jenifer’s decision to continue moving forward within a perpetual learning curve brought about big rewards in the end. More importantly, those growth opportunities weren’t limited to a job description. She is proof that whatever your stage in life, you can expand your skillset.

“New opportunities only appear when we push ourselves to find new ways to grow and expand.”

4. Find a person to emulate and build skills to make it happen.

Your surroundings are filled with skill-building opportunities. “Even when you’re a stay-at-home mom, you can find ways to keep the momentum of your career going,” added Jenifer. “It has been exciting and truly rewarding to raise two young boys and teach them the importance of being a mom and finding a balance between spending quality time with them and providing for our family.”

Jenifer added, “I didn’t have an ideal home life as a child. But, at an early age, there were two things that changed the course of my life: the 4-H Program and a friend’s positive influence.” According to experts, 76% of people surveyed believe mentors are important. But only 37% of us actually have one.

Jenifer believed that both experiences instilled a desire to do something different with her life. “The 4-H Program brought about some great friendships and those relationships showed me a positive parenting role model that inspired me to believe in myself,” she said.

“When I went to the University of Washington, I drove myself to college. I was determined to prove to myself that I could do more. That opportunity to be in 4-H with my friend helped me realize that I could make a better, more rewarding life for myself. And I decided to do it all on my own.”

Jenifer and T-Mobile co-worker Diana Hull snap a photo in their Trailblazer hoodies (2018).

5. Remember: when one door closes, another one opens.

After ten years of marriage, giving birth to two sons, and watching her husband complete his third deployment to Afghanistan, Jenifer was confronted with the reality of divorce. “As I faced this unexpected transition, I knew I needed to not only rebrand my new role as a single parent but also create a professional life that could better support my children and me,” she explained.

As they say, when one door closes, another door opens. That’s when Jenifer found Salesforce. “Through the Salesforce Military Spouse Program, I took courses to get Salesforce certified, and I volunteered to be Director of Technology for the military non-profit wear blue: run to remember Program where I spent one year building out Salesforce Instance for them. The experience I gained while working and learning on that job helped prepare me for my job with T-Mobile, which I love.”

I asked Jenifer how Salesforce has changed the course of her life.

“I took a chance, and it has paid off for my family. I have four Salesforce certifications, and I’m studying for two more including the architect certification. Also, I led a military cohort in 2018. But there’s more to it than that. In this work environment, there is always something more to achieve.” I agree. Those opportunities help grow other facets of your professional and personal life that offer an important connection within the work culture and with customers.

Jenifer believes that for a business to succeed, it must offer voices from different backgrounds, scenarios, and cultures to connect with people and understand what they need. “I represent what I believe our business needs, which are more women working as T-Mobile account executives,” she said. “My experiences have made me want to be an advocate and to be more outspoken for positive change.”

When I asked Jenifer to reflect on her life and the exciting places it’s taken her and her family, she observed that “there’s something satisfying and worthwhile about being out there in the technology world.” And as we learn from Jenifer and arm ourselves with these five life strategies, represent our respective businesses, and promote what we do to a growing woman workforce, we look forward to exciting changes and opportunities ahead.

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Amy Cook
AppExchange and the Salesforce Ecosystem

Amy Osmond Cook, Ph.D., is the CMO of Simplus, a Platinum Salesforce Partner.