High Heels on the Helideck: Captain Alicia Hackshaw’s Flight Path Through Barriers and Bias

The opening session of Caribavia, recently held in St. Barths, wasted no time in tackling a question with far-reaching implications for the region: how can the Caribbean position itself as a magnet for investment in the aviation and aerospace industries?

For aviation professional Captain Alicia Hackshaw, the answer rests on three pillars: skilled people, capable infrastructure, and an unshakable determination to succeed. The Caribbean, she argued, has the talent and training capacity, flight schools, technical centers, maintenance hubs, to compete on the global stage, even in the face of persistent challenges.

Hackshaw speaks from a place of authority. She broke barriers as her nation’s first female helicopter pilot, later serving as Chief Pilot for the Trinidad and Tobago Air Guard and as a Senior Offshore Helicopter Captain with Bristow Helicopters. Today, she sits on the Board of Directors of the Trinidad and Tobago Investment Promotion Agency and works as a Flight Operations Inspector with the country’s Civil Aviation Authority. Her career and insights embody the region’s aviation potential, dynamic, resilient, and ready for takeoff.

This is a 𝘩𝘦𝘳 story, and it's her story.

At 6 a.m., headset in one hand and checklist in the other, Captain Alicia Hackshaw strides toward her helicopter. The sky is just beginning to lighten over the offshore rigs, the wind slicing across the helideck. She is Trinidad and Tobago’s first female helicopter pilot, but even now, in full flight uniform, the question still comes. A rig worker squints and asks, “Wait, you the pilot?”

Her answer is quick and dry. “Nope. I just dress like this to hand out snacks.”

It is a perfect snapshot of the industry she has navigated for nearly two decades, one where helicopters land on moving platforms in restless seas, where every mission is a calculated risk, and where some attitudes toward women seem frozen in another era.

𝐅𝐫𝐨𝐦 𝐂𝐨𝐮𝐜𝐡 𝐅𝐥𝐢𝐠𝐡𝐭𝐬 𝐭𝐨 𝐂𝐨𝐜𝐤𝐩𝐢𝐭 𝐑𝐢𝐠𝐡𝐭𝐬

Hackshaw’s fascination with flight began far from the oil fields. As a child, she leapt off furniture with a bedsheet parachute, turning her mother’s living room into a makeshift wind tunnel. Years later, that same fearlessness led her into one of the most demanding and male-dominated arenas of aviation: offshore oil and gas operations.

Landing a helicopter on a swaying metal dot in the middle of the ocean requires precision, calm, and physical strength. It also demands the ability to handle skepticism from colleagues who are surprised to see a woman step out of the cockpit. Hackshaw learned quickly that in this space, skill is not the only thing tested.

𝐓𝐡𝐞 𝐅𝐢𝐫𝐬𝐭 𝐒𝐥𝐚𝐩 𝐢𝐧 𝐭𝐡𝐞 𝐅𝐚𝐜𝐞

Her first encounter with blatant bias came at 19. Freshly trained and eager for her first job, she walked into an interview confident in her ability. The interviewer, a senior male captain, smiled across the desk and said, “You know, you won’t be able to fly during that time of the month.”

The remark was insulting, dismissive, and rooted in ignorance. She left the room in shock but also with a sharper understanding: she was stepping into a boys’ club where entry would require not just talent but tenacity.

Three years later, she broke through, securing her place in history as the first female helicopter pilot in Trinidad and Tobago. It was not a title handed to her — it was earned through relentless training, showing up every day, and proving herself under pressure.

𝐏𝐚𝐬𝐬𝐞𝐝 𝐎𝐯𝐞𝐫, 𝐓𝐡𝐞𝐧 𝐑𝐢𝐬𝐢𝐧𝐠 𝐇𝐢𝐠𝐡𝐞𝐫

Years into her career, Hackshaw had built seniority, logged thousands of hours, and established herself as a dependable pilot. Yet when a leadership position opened at her first helicopter company, she was passed over without explanation.

Rather than accept the decision, she walked away. Her next step took her into the history books once again, becoming the first female Chief Pilot of an aviation organisation in Trinidad and Tobago. She took command of the national Search and Rescue unit, directing operations, building teams, and leading missions into storms. Under her leadership, no young woman would face the kind of interview she had endured years before.

Her approach to leadership was deliberate. She did not try to blend in or mimic the styles of her male counterparts. Instead, she led with precision, empathy, and a touch of humor, proving that compassion and competence can coexist in high-stakes environments.

𝐒𝐡𝐢𝐟𝐭𝐢𝐧𝐠 𝐭𝐡𝐞 𝐂𝐮𝐥𝐭𝐮𝐫𝐞

Hackshaw is clear-eyed about the changes aviation must make to retain and promote women. In her view, women do not burn out from flying; they burn out from being ignored, overlooked, and under-promoted.

She calls for more than diversity statements. Organisations must create real career paths for women, maintain zero tolerance for casual bias, and establish leadership programs that actively advance female talent.

Her advice to women pursuing leadership is pragmatic: state your ambitions plainly, track your accomplishments, build alliances, and know when to walk away from environments that do not value you.

𝐀 𝐆𝐥𝐨𝐛𝐚𝐥 𝐂𝐫𝐞𝐰 𝐟𝐨𝐫 𝐂𝐡𝐚𝐧𝐠𝐞

Hackshaw draws strength from the work of Women in Aviation International and the International Aviation Women’s Association — networks that provide mentorship, advocacy, and a platform for women across the industry.

She also takes inspiration from other trailblazers: Samantha Willenbacher of Bristow Group, Yvonne Makolo of RwandAir, Sabine Klauke of Airbus, Gwynne Shotwell of SpaceX, and Stephanie Chung of Wheels Up. These leaders, she notes, did not wait for permission. They claimed their place and redefined leadership in aviation and aerospace.

𝐅𝐢𝐧𝐚𝐥 𝐃𝐞𝐬𝐜𝐞𝐧𝐭

Hackshaw’s career has been marked by turbulence and triumph. She has been underestimated, passed over, and dismissed. She has also commanded missions, built teams, and now oversees national aviation safety and regulations. She leaves behind not just a legacy of personal achievement but also a new generation of female helicopter pilots.

Her message to the next wave of women in aviation is direct: you do not need permission to lead. You belong in the hangars, helidecks, and mission control rooms. You do not have to mimic men to lead like a professional. Your instincts matter, your voice matters, and your presence in the cockpit gives someone else permission to dream.

In male-dominated spaces, she says, the goal is not to out-man the men, but to out-lead them. Show up. Speak up. Do the work. Fly the aircraft. The cockpit must adjust to fit the future, and that future includes you.

Go anyway. Show up anyway. Fly it anyway.

𝘊𝘰𝘯𝘯𝘦𝘤𝘵 𝘸𝘪𝘵𝘩 𝘵𝘩𝘦 𝘊𝘢𝘱𝘵𝘢𝘪𝘯 𝘷𝘪𝘢 𝘩𝘦𝘳 𝘐𝘯𝘴𝘵𝘢𝘨𝘳𝘢𝘮 𝘢𝘯𝘥 𝘓𝘪𝘯𝘬𝘦𝘥𝘐𝘯, 𝘦𝘴𝘱𝘦𝘤𝘪𝘢𝘭𝘭𝘺 𝘺𝘰𝘶 𝘺𝘰𝘶𝘯𝘨 𝘢𝘴𝘱𝘪𝘳𝘪𝘯𝘨 𝘭𝘢𝘥𝘪𝘦𝘴 𝘪𝘯𝘵𝘦𝘳𝘦𝘴𝘵𝘦𝘥 𝘪𝘯 𝘢𝘷𝘪𝘢𝘵𝘪𝘰𝘯:

𝘐𝘎: @𝘤𝘢𝘱𝘵_𝘈𝘭𝘪𝘤𝘪𝘢_𝘏𝘢𝘤𝘬𝘴𝘩𝘢𝘸

𝘓𝘐: 𝘸𝘸𝘸.𝘓𝘪𝘯𝘬𝘦𝘥𝘐𝘯.𝘤𝘰𝘮/𝘪𝘯/𝘤𝘢𝘱𝘵𝘢𝘪𝘯𝘢𝘭𝘪𝘤𝘪𝘢𝘩𝘢𝘤𝘬𝘴𝘩𝘢𝘸

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