Executive Management

Brent Handler is Co-Founder of Inspirato and has served as its Chief Executive Officer and a member of its Board of Directors since January 2010. Under his leadership, Inspirato established itself as a leading luxury hospitality company that provides access to a managed and controlled portfolio of luxury vacation homes and other vacation options, leveraging an innovative subscription model to ensure the service and certainty that affluent customers demand. In 2019, Mr. Handler led the development and launch of Inspirato Pass, the world’s first luxury travel subscription that includes all nightly rates, taxes, and fees. Before co-founding Inspirato, Mr. Handler co-founded Exclusive Resorts and served as its President from 2002 to 2009, where it set the standard for the destination club industry. Mr. Handler holds a B.S. in Business from the University of Colorado.

Brad Handler is Co-Founder of Inspirato and has served as its Executive Chairman of the Board of Directors since January 2010, where he focuses on corporate finance and strategic initiatives. Before co-founding Inspirato, he started his career at Apple, then later served as eBay's first attorney. In 2002, he co-founded Exclusive Resorts and served as the company's Chief Executive Officer and Chairman. He has also been a lecturer at Stanford Law School and the University of Virginia School of Law. Mr. Handler earned a bachelor's degree from the University of Pennsylvania, a bachelor's degree from the Wharton School at the University of Pennsylvania, and a juris doctorate from the University of Virginia School of Law.

David leads all operational aspects of Inspirato, with responsibility for the full life-cycle excellence of the membership experience. He specializes in helping service-intensive companies scale infrastructure and technology to drive rapid growth, while deepening the longevity and value of customer relationships. Prior to joining Inspirato, he served in a variety of senior executive roles with Exclusive Resorts, including Chief Operating Officer and Senior Vice President of Sales and Marketing. Earlier in his career he spent 15 years with UPS, where he developed broad operational and logistical expertise, before serving as Vice President for Product and Operations at Visa and in leadership positions with two venture-backed startups.

Robert leads all financial and accounting initiatives for Inspirato. He was most recently with Twitter, where he served as Chief Accounting Officer from 2015 to 2022, helping manage a period of scaling, business model transformation, and international expansion. During his tenure at Twitter, he was responsible for the company’s accounting, financial operations, and finance systems. Prior to Twitter, Robert was with Deloitte & Touche for more than 26 years in several roles, including Partner from 2000 through 2015. At Deloitte, in addition to managing audit accounts with large public companies, he also held significant operational roles and served as Chief of Staff to the CEO of Audit. He is a CPA and holds an MBA from the Wharton School at the University of Pennsylvania, an M.S. in Accounting from the University of Hartford, and a B.A. from Hamilton College.

Web leads Inspirato’s corporate development and strategy efforts. He was previously Inspirato’s Chief Financial Officer, and led the $1.2B merger to take Inspirato public. His experience as a senior executive spans investment and operational contexts, and he has completed more than $40 billion of public and private transactions. Prior to joining Inspirato, he was Executive Vice President of Strategic Initiatives with the Irvine Company, and Chief Financial Officer of Archstone, a former S&P 500 constituent, following its privatization in one of the largest REIT leveraged buyouts in history. Web started his career at Lehman Brothers. He holds a bachelor's degree in Civil Engineering from Oregon State University and an MBA from the Kenan-Flagler Business School at the University of North Carolina, where he was a Kenan-Flagler Fellow and a Wood Fellow.

James joined Inspirato as General Counsel in 2021 and runs Inspirato’s legal team. Prior to working at Inspirato, he started at JetBlue in 2001 and retired as the company’s general counsel and corporate secretary in 2018. He was chairman of private jet and premium scheduled charter companies JetSuite, Inc. and JetSuiteX. James previously served as an attorney at the New York office of Milbank, Tweed, Hadley and McCloy. His aviation legal practice began in airline defense litigation at Condon & Forsyth. James serves on the boards of the National Marine Sanctuary Foundation and the Bob Woodruff Foundation. He received his bachelor’s degree in economics and political science from Boston University and a juris doctorate from Notre Dame Law School.

Michele brings a unique blend of experience in the high-end service industry and brand marketing to her role at Inspirato. As Executive Vice President of Care, she designs and oversees the unparalleled service provided by Inspirato's Care team. Prior to joining Inspirato she operated a large and highly specialized technical account and service team for tw telecom (now Level3, NYSE: LVLT), supporting their Fortune 500 clientele's mission-critical phone, data, and Internet networks. Before transitioning into the high-touch service industry, Michele got her start in marketing, serving three years as the Director of Brand Marketing for Exclusive Resorts and seven years at what is now Century Link (NYSE: CTL) in a variety of marketing roles.

Jeff is responsible for all aspects of Inspirato’s marketing and communications strategy, including brand, new member acquisition, and member marketing initiatives. Before joining Inspirato, he served in a variety of leadership roles with Exclusive Resorts, including Senior Vice President, Marketing and Communications as well as Vice President, Legal. Prior to working in luxury hospitality, Jeff was a corporate lawyer at a large Silicon Valley-based law firm. He began his career as a speechwriter with a trade group in Washington, D.C. and in the Office of the President at the University of Pennsylvania. Jeff holds a bachelor’s degree from the College of William and Mary and a juris doctorate from the University of Virginia School of Law.

Ashlee is responsible for technology and product management at Inspirato including software engineering, data engineering, security, and product design/management. She implements solutions to help Inspirato grow, scale, and achieve its company goals. When Ashlee started at Inspirato in 2013, she was responsible for building out the product management function and several operational teams. Prior to working in luxury hospitality, Ashlee was a technology and strategy consultant, first at Deloitte, then at RAS Consulting, where she was responsible for strategizing and implementing process and technology solutions across oil and gas, healthcare, and financial services industries. She holds a bachelor's degree in finance from Texas A&M University.

Andy leads the finance and real estate operations functions at Inspirato, which includes creation and execution of the business’ annual budget and oversight of Inspirato’s residence portfolio valued at +$1.5 billion dollars. He is an executive sponsor of the Inspirato Foundation, the company’s corporate social responsibility arm. Prior to joining Inspirato, Andy worked in commercial real estate, both as an SVP for a Denver-area family firm with office and retail property, as well as for a multi-family platform with over 7,000 units under management. Additionally, he also has experience in financial services working for Denver-based hedge funds. He holds a bachelor’s degree in European history from Washington & Lee University and an MBA from University of Denver.

Danielle leads people operations at Inspirato, including rewards and recognition, talent acquisition and development, payroll and compensation, benefits, company culture, and engagement. As one of the company’s most tenured senior leaders, Danielle helped grow Inspirato from less than 100 employees to nearly 800-strong today. She is an executive sponsor of the Inspirato Foundation, the company’s corporate social responsibility arm. Before Inspirato, Danielle was a leader in talent acquisition at Vail Resorts, where she hired and retained talent at scale and led teams responsible for staffing five ski resorts. She holds several human resources professional certifications including SHRM-CP, CPSP, and PHR, as well as a bachelor’s degree in human development and family studies from Colorado State University.

As the leader of Inspirato’s sales team, Dain is responsible for welcoming new members to the club and increasing subscription revenue from our existing member base. He focuses on developing sales professionals and strategies, contributions to product development, and technological enhancements to the sales process. His experience in the industry spans 18 years as one of the earliest employees at Exclusive Resorts. Dain left as a Director of Sales after 10 years of serving in various sales and business development roles, joining Inspirato in 2014 as a Vice President of Sales. He holds a bachelor’s degree in speech communication from the Metropolitan State University of Denver and studied abroad at the University of Sevilla.