Our Executive Team at Dragonfly Strategists

In 2016, Caryl Helsel founded Dragonfly Strategists, inspired by a desire to bring expert leadership and strategic guidance to the hospitality industry. After a long and successful career with some of the world’s leading hotel brands, Caryl set out to build a company grounded in excellence, integrity, and meaningful impact.

The name Dragonfly was intentionally selected with purpose. While some business names are crafted for their impact, others for their symbolism, Dragonfly was both a name rich with meaning, deeply personal, and a reflection of the transformation we bring to our clients. The dragonfly represents transformation, adaptability, and forward momentum, all qualities we bring to our clients as we help them evolve and thrive.

Dragonfly is powered by a team of top hospitality talent, each bringing deep expertise across revenue management, distribution, guest experience, sales and marketing, information technology, and operations. We’ve worked alongside iconic luxury brands like Mandarin Oriental and SLS, lifestyle boutique groups like Kimpton and Journal Hotels, as well as midscale and independent hotels, including La Quinta and the historic Hotel del Coronado.

At our core, we are strategists and partners, dedicated to unlocking growth and driving measurable results for hotels around the world.

Caryl Helsel, Founder & CEO

Caryl brings over 30 years of experience in her leadership role at Dragonfly Strategists. Previous executive roles include heading revenue management, distribution, sales & marketing, IT, guest experience and reservations for boutique and luxury hotel companies. She co-authored the original HSMAI revenue management publications that serve as the basis for the CRME industry certification. She served on the board of HEDNA for six years and as president for two. She also served on the board of HSMAI for two years and currently is a member of the Digital and Innovation Advisory Council for St. Jude Children's Research Hospital. Caryl also sits on the board of Stay Boutique and was recently awarded the inaugural TIEWN Fearless Women of the Year award. Having left NYC during Covid 2020, she now resides in Pagosa Springs, Colorado with her husband, son and dog.

R. Scott Helsel, Chief Operating Officer

R. Scott Helsel (Scott) serves as Chief Operating Officer (COO) at Dragonfly Strategists, and brings more than 30 years of experience in various facets of project and account management, program design, training, employee development, operations management, and customer service. Scott oversees the daily operation of Dragonfly including its financials, human resources and employee development. Additionally, Scott is responsible for the oversight of Dragonfly’s comprehensive Projects & Implementations advisory practice. He is dedicated to supporting Caryl, Dragonfly’s Founder & CEO, in executing her vision and initiatives across the organization.

Prior to joining Dragonfly, Scott held progressive levels of responsibility with PricewaterhouseCoopers (PwC) and was a lead producer in its Learning & Development division for nearly 10 years. Previously, he held roles at other high-end firms where he was responsible for complex project migrations, leading teams, as well as developing and launching training curriculums.

Scott holds a B.S. degree in Biology and graduated Cum Laude from Grace College in Winona Lake, Indiana. He is currently working towards a Masters in Organizational Management. He resides in Pagosa Springs, Colorado, and New York City with his wife Caryl, their son, and their four-legged best friend, Quincy.

Alise Deeb, Chief Revenue Officer

Alise joined Dragonfly shortly after our inception to lead our revenue management services practice. With experience from Omni Hotels, Starwood Hotels and LQ Management LLC, she has developed innovative revenue management services, programs, training and operational standards increasing revenues for both franchised and owned hotels. She was invited to be part of HSMAI's Chief Revenue Officer round table and is a frequent industry speaker at events such as STR Data Conference. She sits on the board of the Hospitality Leadership Advisory Board for Missouri State University, her alma matter. An industry thought leader in revenue management and operations, Alise is well-respected throughout the industry. She resides in Dallas with her husband and two dogs.

Amanda Massicotte, VP, Distribution, Technology & Marketing

Amanda brings more than a decade of experience driving marketing, commercial strategy, customer acquisition, and global business integration. Her career includes developing and launching brand loyalty programs, CRMs, and hospitality technology integrations, along with leading commercial and franchise operations with a focus on sustainable growth.

Amanda combines curiosity and a data-driven mindset to craft growth strategies that make an impact.

She has held leadership roles with the Hospitality Sales & Marketing Association International (HSMAI) Arizona Chapter, including serving as Chapter President, and was honored as one of the Top 30 Most Influential Women in Hospitality by Hotel Management.

Amanda is a graduate of the W.A. Franke College of Business at Northern Arizona University. Outside of work, she enjoys hiking, golfing, and spending quality time with her husband and their dog, Eli.

Carol Peach, VP, Sales Advisory

Carol brings a wealth of experience and proven leadership across the luxury hospitality space. She has successfully built and guided high-performing sales and marketing teams for premier hotel brands, from expansive resorts to intimate boutique properties.

Most recently, Carol led commercial efforts at Bardessono and Hotel Yountville in Napa Valley, as well as the Kimpton Armory Hotel in Bozeman. She also played a pivotal role in the successful opening of Rosewood Miramar Beach in 2019.

Her career includes leadership roles at notable properties such as the Inn at Perry Cabin by Belmond, The Roosevelt in Hollywood, and The Westin Market Street in San Francisco.

Carol is known for her thoughtful, hands-on leadership style, grounded in the Golden Rule. She brings deep expertise in direct group and travel industry sales, with a strong track record of collaboration across revenue management, marketing, and public relations. Her strategic mindset and passion for excellence consistently elevate commercial performance.

Evelyne Oreskovich, VP, Projects & Implementations

Evelyne has more than 35 years of experience in travel and hospitality. Most recently she merged her own hospitality consulting agency, HeR Consulting (Hospitality eResources, LLC) with Dragonfly Strategists to bring her extensive project management experience to help Dragonfly’s clients. She has extensive North American and European experience including former senior positions with Trusthouse Forte, Nikko Hotels International, The Leading Hotels of the World, and Pegasus Solutions.

Evelyne has been active and visible in the hotel industry, as a member of ASTA, NBTA, HSMAI and HEDNA.  Along with Caryl Helsel, she was a founding member of HEDNA and served on its board of directors for nine years.  

Bilingual in English and French, with years of international experience, Evelyne understands North American, European and Asian markets, and the corresponding cultures and trends of regional hotel management, marketing, reservations, distribution, revenue, and channel management.

Lauren Epstein, VP, Business Development

Lauren Epstein serves as Vice President of Business Development at Dragonfly Strategists. With an extensive background in propelling revenue growth and forging strategic partnerships, she is known for her unwavering commitment to client satisfaction and a consistent track record of surpassing sales quotes. Lauren’s diverse professional journey includes significant roles at well-known hospitality technology companies such as Booking.com, Amadeus, and Salesforce.

Originally a long-time resident of the bustling city of New York, Lauren recently embarked on a new chapter by relocating to Santa Monica, California, along with her husband and two children. Lauren’s passion for business development goes hand-in-hand with her ability to connect with people on a personal level. Her strategic mindset, coupled with a genuine enthusiasm for building meaningful relationships, positions her as an integral contributor for Dragonfly’s continued success.

Mairead Hennessy, VP, Operations Advisory

Mairead will be integral in transforming Dragonfly Strategists into a full-service Hospitality Advisory Firm, more comprehensive than just Commercial and IT Services. Her strategic vision coupled with her ability to execute operational excellence will be essential to our company’s growth and development.   

Prior to joining, Mairead held senior positions at Hyatt, Hilton, Aramark and Independent brands across Lodging, Casino, Spa, Golf and Food and Beverage, Parks & Destinations industries. Known for her collaborative team approach she has built high performing, cross functional teams that deliver service excellence.

In her 25+year career she has received recognition and awards for her well-respected operational leadership in the industry. She is a self-named Jack Russell Terrier enthusiast and resides in Albuquerque, New Mexico.