"Success is less around the vanity of achievement and more about who I impact.”

My favorite country is: Ask me again once I’ve visited all 195! The superpower I’d love is: To fly – cue Sugar Ray’s “Fly”

Kayla Glanville

Creating a world where travel is safe and supportive for everyone

DISCOVER YOUR CALLING. Kayla Glanville's startup was born out of her passion for mission-driven organizations and a lifelong desire to create a more equitable, compassionate global community. Her company, Upaway, empowers travelers by creating a first-of-its-kind 'travel command center' – an app that makes travel easy by combining auto-organization, destination alerts, and 24/7 on-demand (human) trip support in the palm of your hand.

Kayla's path to founding Upaway can be traced back through her career, emboldening communities by sharing their powerful stories at established brands and cutting-edge startups. In 2013, after graduating from the University of Oregon, she began her career at Nike, helping build their Global Digital Strategy. Joining the company when social media was in its infancy, she reflects on the "incredible privilege" she feels to have worked alongside now-notable leaders in consumer tech.

In 2014, Kayla joined Twitter, motivated by its "town square proposition" and ability to elevate voices and social movements from around the world. While there, she developed its travel industry partnerships, helping travel brands improve their relationships with customers, travelers, and key industry stakeholders. She was also pivotal in turning Twitter's LGBTQIA+ group, TwitterOpen, into a global body, reimagining the company's policies to better care for its intersectional community of employees. A standout moment was consulting on the Obama Administration's White House LGBTQIA+ Technology Advisory Board that prompted the first-ever U.S. Census for transgender folks.

While Kayla's idea for Upaway sparked at Twitter, the impetus to launch it came from a personal experience. When the pandemic thwarted plans for her dream wedding in Mexico in April 2020, she and her wife were left to figure out what support there was from airlines, travel agents and hotels for themselves and – crucially – their 100 internationally traveling guests. "After a month of helping all these travelers with no expert help in sight, I thought, there's got to be a better way.”

"What's interesting is that travel itself is very siloed. Think of airlines, hotels, holiday rentals, etc., each being like neighbourhoods that function beautifully on their own, except no one has thought about how they connect. When travelers find themselves at the intersection of these details, especially across multiple trips, they end up on the receiving end of a firehose of information without much support – and with a ton of frustration."

Before founding Upaway, Kayla conducted a thematic analysis with a diverse sample of 200 travelers to capture the range of issues encountered, including those historically underserved and excluded. The results crystallized the company's philosophy.

"From automatically importing and organizing all of your confirmations, to having realtime safety and trip risk alerts in each itinerary, and having an expert team of 24/7 travel support from industry-certified travel advisors: Upaway is built for travelers, by travelers. We’re not a random call center; we've built a team that reflects the communities we're serving, folks who understand your lived experience and whose sole job is to be in your corner and take the stress off your shoulders."

LEARN, UNLEARN & RELEARN. As Upaway continues its mission to help people travel with peace of mind, Kayla says the company's journey has had an unexpected life-changing impact on her outlook. She's always been comfortable with her identity in the LGBTQIA+ community, but recently being diagnosed as neurodivergent has taken her on a path of unlearning the shame she felt that once caused anxiety and depression.

"When I think about success over the next decade it's not about the vanity of achievement, but about who I impact. It's about creating something that improves lives around the world. It’s invigorating but often overwhelming to build big audacious visions into real world products; I couldn't do this journey without the enduring support of my wife."

"I want to leave people with more opportunity and equity than they had before,” Kayla concludes. If there's a world ten years from now where travel is easier and more accessible, and we've created a more thoughtful, engaged and understanding world through travel, then I'm happy."

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Presented with Pride Here is the first collection of one hundred incredible and inspiring LGBTQIA+ venture-backed entrepreneurs featured in this year's Gaingels 100.