When Jessica Webster was 12 years old, a chance encounter at an airshow launched her career as a pilot and at the same time taught her a valuable lesson about how one man with a gracious and welcoming attitude could open the doors to an incredible career for a young girl. Years later another man slammed that door shut on Webster, who was a pregnant professional pilot, perpetuating mythical objections for rejecting her upgrade to captain and demonstrating that, even in these modern times, the playing field for women in aviation is not level.

However, it was the latter situation that made Webster realize that her assumptions about how far women had come in aviation were questionable, and so she decided to do something about it and founded Hera Aviation Group.

From the beginning, Webster wanted Hera Aviation to be a non-profit resource. The group helps companies figure out how to make aviation more equitable for caregivers, both women and men. She doesn’t want what happened to her to happen to others and figured that there are companies that want to do the right thing but might need some help and guidance.

The event that propelled Webster’s interest in an aviation career happened at an East Coast airshow. Her father and grandfather loved aviation and would bring home pamphlets for the airshows that seemed to occur every summer weekend. “Those pamphlets were to me like the Target toy magazine for Christmas,” she recalled. She would avidly read about the aircraft on display so she knew what to see at each show.

On this particular weekend, the Blue Angels were flying, and Webster made a beeline for a U.S. Navy Lockheed P-3 Orion submarine chaser. While she was reading the description and looking over the P-3, her father and grandfather were talking to the Navy crew standing on the wing. “I was daydreaming, wondering what that would be like [to stand on the wing],” she said, and then the Navy commander asked, “What’s your name? Do you want to come and watch the airshow with us?”

“I was gone like the roadrunner, like smoke, I didn’t even look at my dad,” she recalled. “No sooner did he invite me, I was standing on the wing of the P-3 with all the crew, being welcomed in, being included. It seemed like there were sonic booms, we were so close, I could smell the afterburners of the Blue Angels flying over us.”

Many years later, while recounting the other event that defined her career when she was passed over for upgrade to captain, Webster said, “I thought of how amazing that moment felt of being with that P-3 crew, not feeling different, and how it gave me hope and drive and shaped my fuel to become a pilot. It was pretty poignant and powerful for me.”

Learning To Fly

Webster learned to fly at Beverly Regional Airport north of Boston, washing airplanes in exchange for lessons. Then she earned a bachelor’s degree and commercial and flight instructor certificates and taught at Daniel Webster College in Nashua, New Hampshire. After moving to the UK, she earned her ATPL and got hired at an FBO in Bristol, which led to flying Piper Navajo Chieftains in the challenging weather in Europe on cargo, medical missions, and passenger charter flights. “I flew with some incredible people and learned and loved it,” she said.

After returning to the U.S., Webster got a job in 2008 with a small, family-owned company, flying a Beechcraft Premier 1A on contract. “I love business aviation very much,” she said. “I feel I was born for it.”

Everything was going well; she was flying regularly, both in the Premier 1A and eventually for a different company flying an Eclipse 500 as a contract charter pilot. Her Eclipse training captain recommended she be upgraded to captain, and she became pregnant with her first child. After maternity leave for her son’s birth, Webster returned to work, but something was different.

“Unfortunately, the conversation changed,” she recalled. “Nobody wanted to talk to me about it. It was awkward. The moment that was Hera’s genesis was when I was talking with that captain on a trip.” She brought up the training slot for her captain upgrade. “He got very white, his face fell, and he looked like, ‘I don’t want to have this conversation.’ Then he said, ‘I think you need to talk to them.’”

Webster will never forget the contrast between the joy she felt when the P-3 crew welcomed her into their world at age 12 then years later the fear and disappointment she experienced when she realized that motherhood was going to derail her career.

“I had worked so hard,” she said. “I’m a professional. I’ve always excelled in my position and never had problems on the flight deck or issues with crewmembers. I could not understand what I’d done wrong. But it wasn’t what I did, it was how I chose to grow my family that was the catalyst. I was devastated.”

Finally, when she called the company to ask bluntly why she wasn’t still on the upgrade path, she learned what the leaders really thought: “The conversation didn’t go as I’d hoped. They said, ‘We love you, you’re great, we hope you continue to stay with us. You’re a great pilot, however, you have a son at home and you’re a mom now and your baby needs you and we can’t take the risk.’

“I remember that. I could hear my heartbeat in my ears. I could feel the ache. I advocated the best I could: ‘I’ve been with you guys for years, I ask that you reconsider, this is the value I bring, I’ve never missed a trip or been sick, passengers request me. This is important to my career, to my progression.’ They didn’t reconsider. That was it. I got off the phone and cried.

“That’s the truth. Few male pilots would even have that conversation. It’s not a judgment, it’s a fact. That one moment changed my whole career. That changed my resources, my access, and attempted to change my self-value, my core values. It put in question what type of aviator I was. Nobody should have to do that. Now we have the opportunity to make that different for the next caregiver mother walking through this journey.”

Webster continued flying as a contract pilot in the Premier 1A, but realized that she was “woefully misinformed” about her chosen industry. She had thought that if she worked hard and did her job well, she wouldn’t be subject to discrimination just because she was female. “The imperative to my career was that I continue to grow professionally while being a mother,” she said.

Formation of Hera

In 2015, an opportunity presented itself, a Women in Aviation International scholarship for a Bombardier Learjet 45 type rating. Webster applied, writing a heartfelt essay. She won the Bombardier-sponsored scholarship and in mid-2016 and six months pregnant with her second child, traveled to Dallas for the intensive training and earned the pilot-in-command Learjet 45 type rating along with her ATP certificate.

“It was an incredible experience,” she said, especially meeting the chief instructor, a woman who also had a young child at home. “She was extremely well respected and doing great, and that fueled my hope again that we should not be all painted with one brush.”

After her daughter was born, Webster did some contract flying in a Learjet 45 along with the Premier 1A until the pandemic took hold in early 2020. This spurred her to follow through on her ideas on how to make business aviation more equitable for women. “There are no support facilities in place to help them, and that’s why I decided to bring together an incredible group of women to form Hera.”

The first step was to learn by listening to others about the issues facing women in aviation. “I was surprised,” she said. “I had this altruistic view of where our industry was. I knew I was one of 5 percent that identified as female in my industry. I know there is bias but didn’t know there was that type of bias.”

Another revelation was that despite all the great programs in place to help promote women in aviation, the percentage of aviators who are female has scarcely budged over a long time. “I don’t have all the answers, but I knew I could make an impact. I know about caregiving and know how to solve problems the industry is having. That’s why I decided to move forward with Hera.”

Hera’s mission is “to create positive change for women and primary caregivers in aviation.” This includes working with individuals, businesses, and the industry, Webster explained. “That’s how you effect cultural change.”

For individuals, Hera helps arrange mentorships to help people with career growth, training, and re-entering the aviation industry, as well as support for caregivers like Webster who are balancing parenthood and a career.

While many companies are aware of these issues, Hera can help them figure out how to help their employees by “engaging and actively participating in a solution,” she explained. “We provide solutions for these companies to pivot their leadership and philosophies from this espoused value. To enact that value, there need to be processes in place.”

The benefit of this effort is not just that individuals can keep working in their desired career, but it also helps companies support a more diverse and dedicated workforce, which is ultimately more productive. “It’s not that we should just be a globally responsive industry,” she said. “We know that diverse humans have diverse lived experiences and bring that perspective to any team, which increases collaboration, safety, and efficiency. It’s not only our responsibility, it makes sense.”

Webster makes an analogy between the aviation industry’s adoption of cockpit resource management (CRM) principles and the work that Hera does. At first, the adoption of CRM was a huge cultural change. “Before CRM was largely implemented,” she said, “our flight deck and operations and protocols and procedures were valued very differently. Then smart people got together and said this should be our best practice and this is how we do it. Initially, a lot of people operated from a place of fear. But trailblazers, leaders, innovators, and forward thinkers encapsulated CRM and said, ‘Let’s do this, let’s try.’ What we saw is exactly what I’m talking about. We saw a more harmonized team on the flight deck, and collaboration and safety increased.”

Persuading Leaders

Hera was formed in 2019 and has received a positive response. “People are ready not just to listen but to try it,” Webster said, although she acknowledges that not all companies are run by progressive leaders. “I’m happy to go into a meeting and someone is saying, ‘Why do we need this?’ I’m good at working with them. We can’t be exclusionary and only work with those who are diverse global thinkers.

“It’s important to remember—our beloved industry needs to represent our community. Half of the population identifies as female and a large number happen to be parents. Those unique experiences and diverse perspectives must be valued in our industry.”

However, Hera is about helping all caregivers, not just women. “By working with individuals, companies, and across the industry we will increase aviation’s ability to accommodate the needs of all caregivers, minorities, and the underrepresented, which serves to benefit everyone.” But still, she added, “data shows that women and minorities are more adversely affected—in both frequency and duration—in their careers by primary caregiving, whether it’s caring for an elderly family member, a sick spouse/partner, or for children.”

An example of an organization that Hera helped is a large global company. “They were able to listen and ask a lot of questions about exactly how they can incorporate a more diverse group, specifically caregivers,” she said. This resulted in discussions among company leadership and incorporation of some of Hera’s ideas on diversity, equity, and inclusion (DE&I) in their aviation department. “That’s very innovative for a business to be brave enough to allow us to come together,” she said, “speaking with their cohorts, and hearing what their struggles are and working together to navigate this cultural change that we’re helping to facilitate.”

Hera also helped spread the word as a member of the NBAA DE&I working group, including moderating a forum on engaging caregivers at the 2020 VBACE event.

One of Hera’s ongoing efforts is to help companies with flight departments create flexible workforce models that help caregiving aviators manage their lives and careers. The three models include flexible (part-time), contract commitments, and shared crewmember.

None of these changes happen instantly, Webster pointed out, and it might take time and building a relationship with the company’s leaders, including at the flight department, to help them overcome resistance to the idea of supporting caregivers. And it’s important to help these leaders ask the tough questions, about whether the company really is inclusive, and to be willing to listen to those who have a stake in the discussion. “It’s hard to hear tough things from those you see every day,” she said.

Webster wants to make clear that Hera’s job isn’t to judge anyone but to help them. Hera offers an unbiased viewpoint, someone who can listen and help facilitate conversations about DE&I issues.

“What these organizations are doing is being brave and willing to bring in someone who can help facilitate these conversations,” she said, “to help usher questions and help address reality in a supportive way, just like we require on the flight deck.”

She acknowledges that these companies have grown successful by following their leaders’ vision and developing a strong internal culture. But some leaders might feel that “things are going great here, why create a ripple?”

Culture drives the mission, and leaders need to understand that company culture means something different to everyone, she explained. Leaders do understand strategy, “but what I’ve learned is that culture eats strategy for lunch. That is the point of meeting in the early stages. What would they like to see in their organization, what is necessary not to look at, and what is necessary to look at?

“Hera is not about taking a bullhorn and yelling that diversity is critical. People have been doing that for years. It’s about meeting them where they are and having a conversation about their vision and mission. What Hera can do is not only help them understand from an individual perspective but also understand what leaders can do to transform their culture to be more inclusive, so it becomes welcoming to those things shaped by their vision and mission. 

“We’re not here because it’s popular to talk about,” Webster concluded, “we’re here because it’s important.”