Jennifer Paine and Southwest Airlines Fly in Tandem

The senior director of technology puts innovation and teamwork in play

Working for an airline is, as Jennifer Paine puts it, the ultimate team sport. No position—whether pilot, mechanic, or flight attendant—is able to succeed without the support of other team members. At a company like Southwest—the nation’s largest carrier in terms of originating domestic passengers boarded—that team mentality has a particular resonance. “We fool ourselves if we think that a portion of a person comes to work and a portion of a person is at home,” Paine says. “People are valuable creations who should be appreciated and respected as individuals.”

As Southwest’s senior director of technology, Paine is both a team manager and a coach for many employees. In her day-to-day role, she works as a liaison between the business and technology groups and interacts with members of the operational department, who range from ramp agents to pilots. Paine also determines what each employee group needs and prioritizes those needs within the technology organization to deliver the appropriate solutions. And as a believer in what her team has termed “radical candor,” she also mentors employees throughout the organization, guiding them as they build their careers.

Paine’s interest in technology goes back to fifth grade, when she developed a passion for computer science. As an adult, that hobby bloomed into a career, and prior to joining Southwest, she spent seven years at Neiman Marcus. But Paine’s interest in mentorship, she says, came out of her work over the past ten years at Southwest, which invests in its employees through a team-focused culture and educational opportunities.

Paine’s Passion for Helping Others

Over the past twenty years, Jennifer Paine has regularly participated in efforts to donate hair to create wigs for women who are undergoing cancer treatment. She currently works with Pantene’s Beautiful Lengths program, which accepts donations of clipped hair that reaches eight or more inches in length and has not been chemically treated or permanently dyed. Pantene’s partner, HairUWear, then turns the donated hair into free, real-hair wigs, and the American Cancer Society’s wig banks distribute them.


Managing the company’s technology initiatives has meant working closely with the operational teams to understand the roles they play. “I spend a lot of time learning their business,” Paine says. “Safety is our top priority, and we want to ensure Southwest employees are equipped to do their jobs well. I’ll spend a day in the operations center and sit with various people to understand how they do their jobs so that I’m able to ask questions about what they want automated and how we can stay ahead of the change curve.” From there, her team works on scheduling, execution, and budgeting for both major system transitions and streamlining everyday workflow.

One recent project involved moving crew members over to digital. Southwest—which has more than 3,900 flights each day—recently rolled out fifteen thousand iPads for flight attendants, allowing them to access the extensive manuals used aboard the aircraft. Similarly, pilots have been using iPads since 2013 to access manuals that contain logistics of different airport runways and other communications items. This year, Southwest also rolled out a weather app to allow pilots to monitor updated weather patterns and more effectively maneuver around turbulence, which has translated into fewer injuries. Additionally, having iPads in the hands of flight attendants will allow them to more easily see how many passengers are on their flight, when crews will change, and the status of passengers’ connections in the event of a delay.

Paine is also working to roll out iPads to mechanics, giving them access full manuals on hand to help speed up repairs by ensuring that they’re able to access the information they need.

However, that technology isn’t restricted to tablet computers. “There’s a lot of new tech in the data space,” Paine says. “The whole nature of what a pilot sees in front of the plane has been transforming over the past ten years, and the actual amount of data that’s available to be used is very different as well.”

The airline has also built a new tool that optimizes information during large storms or significant weather disruptions, which allows Southwest to calculate which flights should be canceled or delayed and how customers should be rerouted.

Paine’s goal with each of these updates is to improve how much information is available to those working on the front line. “Ultimately, we have the best employees in the industry,” she says. “By equipping them with information and knowledge, we make it easier for them to deliver the amazing customer service for which they are known.”

“Ultimately, we have the best employees in the industry. By equipping them with information and knowledge, we make it easier for them to deliver the amazing customer service for which they are known.”

That same philosophy led her to a more extended mentorship role at the company. Paine has had more than one hundred members on her team at times, and she always makes a point to have individual conversations with each of them—not just about their work but also about their lives and interests. This includes one-on-one discussions about their role at Southwest, which allows her to identify opportunities for career growth for those individuals and to help them reach their goals by recommending anything from training to changes in their communication style. Over the years, Paine’s directness and willingness to have tough conversations has led to employees throughout the company reaching out to her to seek advice and feedback.

This investment in people, Paine says, has become her passion area at the company, something that she hopes to do more of down the road and something that she sees ultimately benefiting the culture.

“There is a tangible result, in that when you invest in people and help them feel valued, they produce more and are willing to run through walls if you need them to,” Paine says. “I really do feel that my value at Southwest is centered around investing in people and making a difference in people’s lives, which also makes a difference for the company.”

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