Jessica Power started with a straightforward goal: earn her private pilot certificate, a dream she’d carried for years. What emerged instead is Westerly Aero — an established flight school she acquired and rebranded, and is now building while still working toward that certificate herself. She is currently in the process of closing on an airplane for the school.
Power announced the venture publicly this week. For someone with more than 25 years in aviation, the timing carries a certain symmetry: her first job out of college was in aircraft sales and acquisitions. Two and a half decades later, she’s buying an airplane for a flight school of her own.
An Unusual Path In
Most flight schools change hands between people who came up through the training side — instructors, chief pilots, operators who have run one before. Power’s route is different.
Her professional background is in aviation marketing and brand strategy — guiding aviation companies through storytelling, positioning, and relationship-driven growth. That means she arrives at Westerly Aero with something many new owners lack: a quarter century of industry relationships, and a working understanding of how aviation businesses actually reach the people they’re trying to serve.
Acquiring an existing operation rather than starting from zero has real advantages. There’s an established customer base, existing procedures, and — critically in flight training — a working relationship with instructors and the local airport. The rebrand to Westerly Aero signals that she intends to build something of her own on that foundation rather than simply continue what was there.
What she does not yet have is the certificate. Power has been candid that she is still working toward her PPL while running the company — and she has framed that as part of what makes the effort meaningful rather than something to work around.
There’s a case that it’s an asset. An owner currently going through flight training has unusually direct insight into what the experience is actually like: the scheduling friction, the cost anxiety, the plateaus, the difficulty of getting a call returned. Those are the problems flight schools most often fail to solve, and they’re easier to see from inside the student’s seat than from the front office.
The Broader Vision
Power has been explicit that the ambition extends past operating a training business.
Her stated goal is to use the relationships and experience accumulated over 25 years to help people find their place in aviation — which for some means becoming a pilot, and for others means discovering a career they didn’t know existed, connecting with a mentor, or simply learning that there’s more than one way into the industry.
That framing matters more than it might sound. Aviation’s workforce challenges are substantially problems of awareness rather than capacity. Roughly a third of aviation maintenance technician school seats sit unfilled nationally, and industry groups have repeatedly identified visibility of career paths — not training availability — as the binding constraint. A flight school that treats itself as an on-ramp to the whole industry, rather than only to a pilot certificate, is addressing something real.
Early Days
Power has acknowledged the transition has already hit turbulence, and that considerable work remains. That candor is worth noting in a space where new ventures tend to announce themselves as fully formed.
Taking over an existing operation, adding aircraft, and establishing a new identity are each substantial undertakings, and the flight training market is not an easy one — Redbird’s State of Flight Training 2026 report found that 18% of small flight training organizations are not profitable, with margins scaling by size. Ownership transitions are a particularly demanding period, since students and instructors both watch closely to see whether service holds up.
But demand is there. Training inquiries have grown sharply across the industry, most prospective students want to start within weeks rather than months, and the majority are at the very beginning of the pipeline. A school led by someone who understands both the industry and the experience of being a student pilot is well positioned for that audience.
The Bottom Line
Westerly Aero is at the beginning of a new chapter — an established school under new ownership and a new name, an airplane in the process of closing, an owner still working toward her own certificate, and a stated ambition to help people find a place in aviation whether or not that place is a cockpit.
It’s a good story, and a reminder that the paths into this industry are less linear than they look from outside. Someone who set out to learn to fly now owns the thing that teaches other people to fly, using a career’s worth of relationships to do it.
More information is available at westerly-aero.com.
Frequently Asked Questions
What is Westerly Aero? Westerly Aero is a flight school acquired and rebranded by Jessica Power, an aviation professional with more than 25 years in the industry. She purchased an existing flight school and changed its name as part of the transition. The company is currently in the process of closing on an aircraft. Power’s stated vision extends beyond flight training to helping people find their place in aviation more broadly, including career discovery and mentorship. More information is at westerly-aero.com.
Who is Jessica Power? Jessica Power is an aviation professional whose career spans more than 25 years, working in brand storytelling, strategy, and relationship-driven marketing for aviation companies. Her first job after college was in aircraft sales and acquisitions. She is currently pursuing her private pilot certificate while leading Westerly Aero.
Can you own a flight school without being a pilot? Business ownership and pilot certification are separate matters. Flight instruction must be delivered by appropriately certificated flight instructors, and operations must meet applicable FAA requirements under Part 61 or Part 141, but the owner of a flight training business is not required to hold a pilot certificate personally. Many aviation businesses are led by people whose expertise is operational, financial, or commercial rather than in the cockpit.
What challenges do flight school owners face? Flight training is a demanding business. Redbird’s State of Flight Training 2026 report found that 18% of small flight training organizations operate unprofitably, with profit margins scaling by size — roughly 12% for small operations compared to 18% for large ones. Owners face aircraft acquisition and maintenance costs, instructor recruitment and retention, insurance, and competition from established operators. Ownership transitions add their own difficulty, as students and instructors watch closely to see whether service quality holds through the change.
Why does aviation career awareness matter for flight schools? Industry workforce shortages are driven substantially by awareness rather than training capacity — roughly one-third of aviation maintenance technician school seats nationally go unfilled, largely because prospective students don’t know those careers exist. Flight schools that position themselves as entry points to the wider industry, rather than solely as pilot certificate providers, can serve students whose best path may be in maintenance, dispatch, airport operations, or another discipline.
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