TripWorks, the operator-built platform transforming how tour and activity businesses manage pricing, automation and growth, today announced the expansion of its leadership team and the continued guidance of two seasoned executive advisors. The update follows the company’s recently announced Series A funding round and marks another major milestone as TripWorks scales to meet rising demand for smarter, more predictive operator technology.
The announcement comes at a time of significant momentum across the experiences sector. Operator revenue is expected to surpass pre-pandemic levels this year, signalling a renewed surge in demand. At the same time, nearly 40% operators worldwide still do not use a reservation system, highlighting a substantial technology gap TripWorks is uniquely positioned to address.
“As the experiences industry evolves, operators are asking for tools that help them grow without adding complexity,” said Aaron Fessler, Founder & CEO of TripWorks. “This leadership team brings the operational depth, product expertise, and customer-centric mindset needed to deliver exactly that.”
TripWorks’ key leadership appointments bring extensive experience across product, operations, customer success, revenue, and technology – all critical functions as the company accelerates development of its AI- and BI-powered platform. Notably, the team is now 50% female, reflecting TripWorks’ commitment to building a diverse leadership bench in an industry where women remain underrepresented in senior technology roles:
- Aaron Fessler, Founder & CEO – A serial entrepreneur with a background in building and scaling technology companies, Fessler founded TripWorks with a mission to give operators modern tools built with real operator DNA.
- Mara Kaufman, EVP, Operations – An operations and customer experience specialist with more than 15 years’ experience scaling teams and processes in fast-growing technology environments, including senior positions at Doctor.com
- Chris Cheesman EVP, Finance, – A finance leader with significant experience at large corporate brands, including senior positions at PWC
- Melanie Gannone, Director of Product – A product leader with experience driving user-centric innovation across high-growth SaaS platforms
- Jana Glassman, VP of Sales – A sales leader with a proven track record of driving high-revenue growth for travel tech software companies – specialising in the experiences industry.
- Mimi Assefa, Head of Marketing – A marketing and growth leader focused on helping operators adopt technology that drives business impact, who previously held leadership positions at Doctor.com.
TripWorks’ Series A funding, announced last week, is fueling rapid product development across dynamic pricing, predictive insights, automation and business intelligence. The expanded leadership team will accelerate this work as the company continues to grow its customer base across the experiences sector.
“This group understands what it takes to scale a high-growth platform while staying focused on what matters most: delivering real value to operators,” Fessler added. “With our full team in place, we have one goal: to give operators the tools and insights they need to grow revenue, streamline operations, and deliver exceptional experiences to travelers. The industry is changing fast – and we’re building the technology that helps operators stay ahead.”
Executive advisors continue to guide AI, BI and global expansion plans
TripWorks also continues to benefit from the expertise of two long-standing executive advisors:
- Gary Millin – Founder and CEO of World Accelerator and an early-stage investor with a long track record of supporting transformative platforms. Entrepreneur who founded Mail.com, growing it into a $1 billion NASDAQ company.
- Andrei Zimiles – A founder, operator, and multi-exit entrepreneur with deep experience in scaling technology companies and navigating complex marketplaces. Previously founding CEO at Doctor.com.
Commenting on TripWorks’ growth journey, Gary Millin, President of World Media Group, said: “TripWorks is at the forefront of innovation, applying practical AI to the moments that actually move the needle for large operators. The platform strengthens the booking journey end-to-end, from discovery through conversion, improving pricing, forecasting, and day-to-day operations. The result is faster and more profitable growth for operators worldwide.”
Their guidance strengthens TripWorks’ ability to innovate quickly, expand globally, and build the predictive, automated infrastructure operators increasingly rely on.
