How Southwest’s CIO modernized the airline through turbulence

Taking the helm as CIO is a major transition for any IT leader, but Lauren Woods’ experience at Southwest Airlines stands apart.

Two months before she was officially named CIO in February 2023, Southwest experienced one of the largest operational disruptions in aviation history, right in the middle of the busy holiday travel season, with outdated software systems at the center of the meltdown. 

Southwest CEO Bob Jordan later attributed an imbalance in the company’s growth mindset and a lack of investment in digital transformation as central causes of the travel disruptions the airline incurred during the December 2022 holidays. Focused on growth, the company’s leadership had deprioritized modernizing internal systems, hiring IT staff, and updating internal processes to keep pace with its growth agenda. The result was a PR firestorm with more than 15,000 cancelled flights, unprecedented refunds and reimbursements, a $220 million revenue loss during Q4, and a $140 million civil penalty when the dust settled.

Woods was thrown directly into that deep end, with little time to adjust to her new leadership position. She calls it an “accelerated learning opportunity,” noting that when you take on a new role, you typically expect around six months to learn and grow into the position.

Woods didn’t have that luxury. Instead, she found herself facing not only an accelerated learning curve, but also “accelerated visibility.” Almost immediately, all eyes were on her as she sought to right Southwest’s operations.

“That was interesting because I think some of the top leadership who knew of me and supported me into this role really hadn’t seen me,” she says. “So now they got to see me in action.” 

Leading during turbulent times

Woods’ background leading transformative initiatives at Southwest, as well as her approach to leadership that she has developed throughout her tenure leading IT teams, suited her well in taking over IT as the airlines was plunged into chaos.

Leaning on those bona fides, Woods rallied and guided her teams to overhaul Southwest’s technical operations with a shared commitment to doing right by the customer. In fact, customer solutions is where Woods began her tenure at Southwest 14 years ago, having signed on to manage Southwest.com during a time when the company was transitioning from C++ to Java, and adopting agile development methodologies.

Woods spent the next decade learning the ins and outs of Southwest’s commercial side, supporting the transition to a new reservation system, integrating new systems when the company bought AirTran, and eventually moving into more integration work across the company, before coming back to the front-end part of the business as a director.

When Kathleen Merrill, then SVP of technology and CIO, tapped Woods to work on operational systems, Woods was hesitant because the bulk of her experience was on the commercial side. But Merrill recognized that Woods understood software development and had both a strong working knowledge of the airline and deep domain expertise — all of which singled her out as a strong candidate to make the shift.

“I ended up leaning on my partners in the business and learning so much from them about how our airline worked and what it was like on the operational side,” she says. “It gave me insights into how important data, cloud technologies, and other things were that we really needed at that time.”

As Southwest embarked on its cloud transformation, Woods was promoted to vice president of technology platforms and architecture, taking on larger digital transformation and modernization responsibilities along the way. And in September 2022, Woods was announced as incoming CIO, set to take over the IT mantle from Merrill in February 2023.

Woods says the experience navigating Southwest IT through that turbulent period was a time of extreme personal growth, forcing her to dig into the executive role and identify what was needed from her, showing up for her team, and leading them to better organizational footing. While the events that led to Southwest’s most recent modernization were regrettable, Woods and her colleagues are proud of what has come of their efforts.

“We’re a better airline for it,” she says.

Woods benefitted from the fact that Southwest IT had already embarked on a modernization journey when she was named incoming CIO. The December 2022 meltdown simply pushed the company to accelerate that process, with a focus on updating outdated and irregular operations throughout the business.

One key issue Southwest faced during the 2022 holiday meltdown included mass flights cancelations due to operational systems struggling to recover from the initial weather-related disruptions, rendering the company unable to locate crew members at times to staff flights. Woods and her teams addressed this issue by building a tool called Crew and Aircraft Integrated Recovery and Optimizer (CAIRO).

According to Woods, CAIRO is “the first of its kind,” enabling Southwest to automate, prioritize, and reset the crew and aircraft networks simultaneously and flag potential flights that might need to be cancelled, while minimizing the potential impact on crew members.

Woods’ team was also supported by work they already did in response to COVID-19, which pushed them to focus on core data foundation changes. These made it easier to implement real-time data streaming, reducing the time to pull data from an hour or more, to just minutes.

Authenticity and courage

Woods also credits company leadership with helping her team successfully accelerate the work, noting that she had the full support of the executive team, who were open to hearing what needed to be modernized, what needed to be improved, and where the biggest investments needed to be made.

“So that’s where we’re focused — making sure we have these reliable and effective systems so we can create that competitive advantage where we want to be focused on being able to produce a really good product, because we have really great customers,” she says.

As CIO, Woods oversees a “wide breadth of work and focus,” as technology plays a role in every part of the business, from airline bookings, to staff scheduling, to the financial systems that keep the company afloat, she says.

Prior to coming to Southwest, Woods worked in consulting, an experience she feels helped make her the leader she is today. As part of that work, Woods became very familiar with navigating situations in which she was the only woman in the room — a reality she says she has never shied away from. As she has advanced her career, Woods has made a point to identify leaders she can learn from, as well as those she doesn’t want to emulate. Despite working in a male-dominated industry, Woods says she’s also been fortunate to have several women leaders who came before her at Southwest, including Kathleen Merrill, who was VP of strategy when Woods joined 14 years ago, as well as EVP and CFO Tammy Romo, Chief Administration Officer Linda Rutherford, and SVP of Customer Experience Teresa Laraba.

“What was amazing about Southwest was that when I came in, there was a good amount of female leadership. That was a wonderful opportunity for me as a young leader to come in and say, ‘Okay, I see myself there.’”

That representation proved to be a cornerstone as Woods developed her leadership style, and seeing other women leaders in the organization helped her envision a similar path forward for herself. She found herself drawn to authentic leaders, especially women who weren’t concerned with being “perfect,” and who showed up as their true selves at work.

“A lot of times when we are coming up in our careers, we see people who seem very experienced,” she says. “You get the elder statesman, the very quaffed female leader, and I didn’t relate to any of those. I want to be very authentic. I like to lean into being very courageous, but I’m also very much not perfect.”

In developing her leadership style, Woods has identified authenticity and courage as her primary values. To Woods, authenticity is important because she feels it’s the only way she can show up as her best self; courage meanwhile enables her to handle the difficult aspects of her leadership roles effectively, whether it is having difficult conversations or being critical of processes and platforms.

“I always want to lean into that courage, but I want to do it in an authentic way that matches my values. I want to be kind and respectful, even if I have to be tough and hard. I want to find clarity in my role, and my team needs that clarity from me. And then I need to seek that clarity from my stakeholders and executive leaders,” she says.

Those values served Woods well as she navigated one of the hardest transitions a CIO can endure.

While Woods recognizes that leadership approaches can be shaped by those who came before you, when it comes to mentors, Woods advises aspirational leaders to ensure that they aren’t only looking above them for mentorship. While it’s important to learn from and make connections with leaders in the organization, you can learn just as much from peers in your organization, or people outside your department or career path, she says.

“I think there’s a lot of people who look for mentors to be your boss, or somebody who’s already in these positions,” she says. “And I’d really encourage women to look for people willing to invest in them regardless of their position, because some of the people who were most influential to my career aren’t executives.”