Hera Aviation Group is a coaching and development-based consultancy group and nonprofit organization. It works with individuals, organizations and industry to transform culture by cultivating connections that disrupt the status quo of today’s workplace and empower women and primary caregivers to grow their careers in aviation. We asked Founder and President Jessica Webster a set of questions that she answered with candid honesty:

Women Leading Travel & Hospitality: How did you get your idea or concept for Hera Aviation Group? How did you choose the name?
Jessica Webster:
“We can’t take the risk.” The genesis for Hera Aviation Group was born from the complete and utter demoralization of being passed over for a captain upgrade simply for becoming a mother. I was a skilled pilot operating for a charter company that passed me over, with a previous commitment, for a captain upgrade solely for having chosen to grow my family. Upon listening to hundreds of similar stories, I realized this was a rampant practice of systematic bias in the aviation industry. While sitting on the floor of my dear friend’s home office, drinking my Starbucks, Hera came to be.

Hera Aviation Group’s name comes from the Greek goddess Hera: the goddess of women, marriage, family and childbirth in ancient Greek religion and mythology. Hera also rules over Mount Olympus as queen of the gods. She was known for her fierce bravery, incredible leadership and nurturing love. She was celebrated for her integration of self.

Hera embodies all that I hoped our nonprofit would represent.

WLT&H: What was your mission at the outset? What was your key driving force to launch Hera? Has it changed?
JW: Our mission remains the same: empower individuals, cultivate change, and transform the aviation industry to make it more representative of our community; more equitable, diverse and inclusive.

The only thing that has changed is the dedication of this team. Having done the leg work and spoken to so many others who are hungry and ready for this culture revolution, our research identified the paucity of data surrounding our cohorts. We can’t manage what we don’t measure. Seeing this gap in value, our team has a deeper conviction now than when we formed Hera Aviation Group. We’re firm in our belief and passion that caregivers are capable and dedicated employees if we can just create the systems and tools for them to thrive in.

Caregivers deserve to belong.

WLT&H: How has being an entrepreneur affected your family life?
JW: Within my own family, we have to be very structured. We’re a family with special needs. Structure is a necessity for happy coexistence. I’m familiar with the lack of balance that always pursues progress and an ever-searching integration of home and profession. Sometimes it feels like I’m chasing the sun. I have to be intentional with the time I spend on Hera Aviation Group, usually after the littles go to sleep, because I’m a primary caregiver. Anything less than being present causes chaos and anarchy at home.

The unexpected influence my work within Hera has given us is a deeper sense of consciousness to service my littles have represented. They see my conviction and commitment and model it in such sweet ways! My four-year-old daughter recently shared with me that I make up 25 percent cuddles, 25 percent protect her babies, 25 percent love, and 25 percent work. I couldn’t be prouder. That will make a great Hera T-shirt.

WLT&H: What is the biggest hurdle in starting something new?
JW: There’s a consumptive energy when creating an organization. The structure of our nonprofit grows much quicker than there’s time to adapt and reform. I find that the biggest hurdle is the amount of organization that’s required to keep up with progress. It’s a great hurdle to have, but equally challenging to achieve!

WLT&H: What’s your company’s goals?
The disruption of DE&I and caregiver practices in business aviation is real. We don’t have the same amount of diversity as other industries, but we can get ahead and create a toolkit together to solve these issues in our profession and advance these critical DE&I activities. We see so much that aviation can breed a family-like culture because of the close-knit ties we keep through our careers. This is just a way to extend that gracious table to more of us. I can’t think of a single reason that having more people to contribute in different ways won’t benefit the service we provide our clients and help us stay in business.

Using these highly qualified but underused pilots to contribute to the demanding schedules of business aviation should be seen not as filling in the gaps, but creating more of an interwoven mesh to strengthen and complement the needs of the business.

  • High-level cultural assessments with corporate aviation departments to help enact a more inclusive culture in their departments.
  • Build new retention policies and recruitment practices for women and primary caregivers.
  • Secure commitments of organizations to utilize and integrate caregiver aviators in their aviation departments for 2021 initiatives through our Hera Diversity Equity and Belonging program.
  • Research partners with universities to address the paucity of data with women and caregivers in aviation; explore the retention issue of caregiver aviators.
  • Coach and develop organizations with aviation departments through the implementation of flexible workforce models for women and caregiver aviators.
  • Empower individuals to grow their careers through our mentorship platform.

WLT&H: What motivates you?
JW: I’m moved by the tenet that in my lifetime we will see the aviation industry adapt to the needs of those that shaped it. I endeavor to see a shared responsibility in creating a culture where we all belong. I’m motivated by my Littles and my Tribe. They’re just the coolest people I know.

I put my feet on the floor in the morning and say to myself, “To thine own self be true.” I’m motivated to create space for the aviation industry to value us all as women and caregivers in all the ways our culture espouses value.

WLT&H: What is your greatest fear, and how do you manage it?
JW: When I allow doubt to creep into my thoughts, “inconsequential” is the word that makes my chest tight. When I feel the possibility of not mattering hold more weight in my heart, I speak out against it. I’ll say out loud what I want to manifest instead.

I also practice mindfulness to combat the fear to bring me back to where my feet are, which is in the present moment. I reach out to people I trust and share the burden. I listen and take suggestions on how they walk through their fears.

The only way out is through! There’s always a light at the end of the tunnel. No matter what happens with Hera Aviation Group, we already matter! We matter to the lives of all the caregivers that want to belong.

WLT&H: What has been your most satisfying moment, from planning, to launch, to now?
The most powerful moments in this journey with Hera Aviation Group have been the emails of thanks, the identification and inclusion coming from the shared stories of the women and caregivers that have been uncounted and marginalized in aviation. Their hope is our triumph.

WLT&H: To what do you attribute your success?
JW: Every single ounce of success is not mine. My success stands on the shoulders of all the humans that came before me: my family, who taught me to be kind and brave; my tribe, who show me I’m enough by caring for me, working with me, pushing me, laughing with me and crying with me; my mentor, who teaches me that I can fail and still be an incredible leader by accepting me as I am, emulating that which I want to be in life and business.

I’m truly grateful.

WLT&H: If you had one piece of advice to someone just starting a new organization or company, what would it be?
JW: It’s been my experience that it’s super important to follow your heart and trust your belly. No matter what happens, if you do the next right thing, the next right thing will happen.

WLT&H: What piece of advice would you give to someone that wanted to go off on their own?
JW: I’ll tell you what everyone tells me: If you follow the little voice inside your belly, the vulnerable one saying, “Hey, should we do this?” no matter how soft or loud it is, if you decide to walk along that path, you’ll be OK no matter what.

At times, when I meet with my mentor, he offers to me that he doesn’t know the future of Hera Aviation Group and the measure of its success, but no matter what, I’m growing. I’m becoming. I’m right where I’m supposed to be.

WLT&H: What would you say are the top three skills needed to be a successful entrepreneur?
JW: Having authenticity, empathy, and the ability to be adaptive are skills I personify as an entrepreneur.

WLT&H: Who has been your greatest inspiration?
JW: My mother and grandmothers. They all raised me to be the woman I am today. They showed up, over and over, sacrificing themselves and society’s measure of their own success so that I could be here typing this answer today. They exemplify my strength, my honesty, my relentless determination and my ability to stand up when I fall.

Jessica is a mother, partner, and career pilot residing in New Hampshire. She is a private executive jet captain with 20 years in the aviation industry. 

Prior to founding Hera Aviation Group, Jessica worked as an international contract pilot; a collegiate adjunct; flight instructor and flight team coach at Daniel Webster College; a senior duty officer for Gold Air International in the United Kingdom; and an operations officer at Bristol Flying Centre. Jessica is a member of Women in Aviation International, the National Business Aviation Association, Massachusetts Business Aviation Association, and served as a board member for The Ninety-Nines organization. She is also a transition coach for Gatehouse Treatment.

Jessica has authored several articles on gender parity, equity, diversity, and inclusivity, and has been featured on the “New Hampshire Chronicle” television program about prominent female aviators. She was also a Women in Aviation International scholarship awardee, and serves on several industry discussion panels. She has a Bachelor of Science in Aviation Flight Operations from Daniel Webster College.