Southwest Hawaii Strategy Power Play: Marketing From United Airlines

Southwest plans to address its system-wide operational hurdles, strengthen customer loyalty in Hawaii, and attract new travelers to remain highly competitive in the islands. To this end, they’ve lured United Airlines marketing guru Aileen Furlong to the Southwest team. Starting in January, she’ll be Southwest’s new Vice President of Sales.

Furlong brings over two decades of solid experience at United Airlines, including leadership roles in three areas pivotal to Southwest in Hawaii: marketing, corporate sales, and loyalty programs. Her expertise aligns with Southwest’s urgent need to define its Hawaii strategy and regain an edge in a market that’s become more competitive than ever and appears to be slipping from Luv’s grasp.

This leadership move reflects broader changes at Southwest, as the airline seeks to address multiple weaknesses. Furlong’s appointment signals a bold step forward that will significantly impact Southwest’s Hawaii plans.

Leadership dynamics: United’s Furlong joins Hawaiian’s Ex-Andy Watterson at Southwest.

Furlong’s arrival highlights fascinating dynamics evolving within Southwest’s leadership. Andy Watterson, who played perhaps “the” pivotal role in Southwest’s Hawaii expansion, joined the airline from his executive position at Hawaiian Airlines. His efforts helped Southwest establish interisland flights and low-cost transpacific options, clearly disrupting the market long dominated by Hawaiian Airlines and United.

We’re going into a new world with our new product… which will be underpinned by our new industry-standard product: assigned seating and extra legroom.” — Andrew Watterson, Southwest Airlines

However, recent investor dissatisfaction with Southwest’s top leadership, including COO Watterson and CEO Bob Jordan, raised questions about potential changes and may have led to this latest addition.

Could Furlong’s appointment signal a broader shift in Southwest’s focus on Hawaii? With her strong corporate sales and loyalty background, she brings what appears to be a fresh and needed perspective to Southwest’s Hawaii strategy too.

Hawaii flights may refocus more on loyalty and corporate travel.

Southwest’s success in Hawaii has relied heavily on low fares and operational simplicity, but the airline has struggled to match its competitors. Alaska and Hawaiian Airlines have strong ties to Hawaii and West Coast communities, while United’s MileagePlus program has kept frequent travelers loyal.

Southwest’s Rapid Rewards program may see big and important Hawaii-specific improvements under Fulong’s leadership. That could include a program matching or even beating the new Huakai by Hawaiian local benefits program for Hawaii residents. And maybe more is coming, including targeted promotions, partnerships with strategic Hawaii businesses, or even enhanced offerings for corporate travelers—segments where Southwest has room to grow and has lagged.

Corporate travel is an area where Furlong’s expertise could well shine with Hawaii as a long popular destination for business retreats and conferences, and Southwest could expand its reach in this lucrative and perhaps resurging market with more tailored offerings. If Southwest can successfully leverage Furlong’s experience, it may finally bridge these gaps. If not, its foothold in Hawaii could weaken further.

Competing for Hawaii travelers.

Southwest’s entry into Hawaii initially shook the market, offering far more affordable options for transpacific and interisland flights. But the airline has struggled to maintain that early momentum. Operational issues, including the recently announced Hawaii flight cutbacks set for 2025, have chipped away at customer satisfaction and left some wondering about Southwest’s long-term commitment to the islands.

With Furlong on board, Southwest may rethink how it approaches Hawaii. Her extensive airline experience demonstrates a sharp understanding of navigating competitive landscapes—perhaps even one as distinctive as Hawaii.

If Southwest can channel her expertise, it might develop strategies to better connect with Hawaii’s leisure and business travelers, potentially regaining ground in this crucial market.

What this means for Southwest’s Hawaii future.

Southwest’s Hawaii strategy has been a cornerstone of its past five years of expansion. However, sustaining growth and achieving financial success in the islands requires more than the airline has offered. Furlong’s hire signals a renewed focus on marketing, loyalty, and corporate sales—key areas where Southwest must stand out in an increasingly crowded Hawaii air market.

As Furlong teams up with Hawaii guru Andy Watterson, the question remains: Will this high-profile new team elevate Southwest’s Hawaii presence to the level now demanded by the market?

We’d love to hear your thoughts.