Steve Upshaw
Steve Upshaw Chief Executive Officer

Steve has 20+ years delivering consumer services via business partnerships and direct-to-consumer programs.

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Steve Upshaw
Steve Upshaw Chief Executive Officer

Steve is at the helm of the company’s high-level strategy and robust growth efforts.

Since taking on the CEO role in 2015, Steve has been the driving force behind impressive year-over-year revenue growth, ongoing margin expansion and an aggressive campaign to continuously improve the customer experience. Under his leadership, Cinch has doubled in size over the last four years, embraced a new tech-forward philosophy and adopted a refreshed brand identity.

Prior to joining the company, Steve served as president of Affinion Group and CEO of Global Engagement Solutions where he helped improve and streamline clients’ customer engagement programs, build brand loyalty and drive revenue growth for thousands of marketing partners worldwide. During his tenure with Affinion Group, he served in a variety of capacities with progressive responsibility, including five years as CEO of Affinion International. Steve’s other previous roles include CEO of Global Financial Services, CEO of Affinion North America, and COO of Affinion Group.

Steve holds a Master of Business Administration from Texas A&M University’s Mays Business School. He also serves on the board for the Orange Bowl Committee, a South Florida-based organization dedicated to growing tourism, supporting student-athletes and assisting children and families in the community.

Richard Outram
Richard Outram Chief Financial Officer

Richard leverages over 30 years of industry experience to lead all financial and administrative activities.

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Richard Outram
Richard Outram Chief Financial Officer

Richard leverages over 30 years of industry experience to lead all financial and administrative activities.

He works hand in hand with CEO Steve Upshaw and the rest of the executive team to drive growth and carry out the company’s tech-forward strategy.

Richard’s prior experience includes CFO positions in public, private and private equity companies, including IC RealTech Inc., Signature Consultants LLC, PRC LLC, and Stock Spirits (USA) Inc. He has deep experience in leading companies through various life cycles and scaling businesses for profitable growth. Richard is also a certified public accountant, certified management accountant and certified fraud examiner in both the United States and United Kingdom.

Originally from the UK, Richard earned his ACCA in accounting and finance from North London University. He currently serves on the board of directors for Step Up for Students, a nonprofit providing low-income and special-needs students with scholarships covering tuition, textbooks and therapies. He is also the former president and a current board member for Financial Executives International’s South Florida Chapter, an organization dedicated to advancing ethical and responsible financial management.

Doug Stein
Doug Stein Executive Vice President

Doug leads the business-to-business organization, which serves the financial, insurance, real estate, retail and utility markets.

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Doug Stein
Doug Stein Executive Vice President

Doug leads the business-to-business division, which serves organizations across the financial, insurance, real estate, retail and utility industries.

In this capacity, Doug also oversees sales, marketing and client-management efforts in support of some of the nation’s largest and most successful companies.

Prior to joining Cinch, Doug was an executive at Accenture, a leading global services company, where he focused on domestic and international projects in corporate strategy, global program management and key business account development. During his tenure at Accenture, Doug gained experience in the intersection of business and technology, helping clients improve their performance and create sustainable value for stakeholders.

Doug holds a Master of Business Administration from Northwestern University’s Kellogg School of Management and is currently the president of the National Home Service Contract Association, representing the home warranty industry. He is also a board member of the Real Estate Service Provider’s Council.

Chris Askew
Chris Askew Chief Operating Officer

Chris leads both the operations and technology organizations, ensuring continuous innovation in our service to customers.

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Chris Askew
Chris Askew Chief Operating Officer

Chris oversees operations and technology efforts, as well as other administrative functions.

In this role, Chris is responsible for the management of the company’s various state-of-the-art customer service centers, nationwide service technician network, corporate IT strategy, operations and development and a host of other related functions. This integrated scope — combining the development of customer-driven service practices with new technology applications — is essential to the organization’s goal of driving digital transformation both internally and across the entire home services industry.

Previously, Chris was president of services at Best Buy, where he oversaw the Geek Squad and service-contract business. His impressive experience also includes high-level executive roles at global technology corporations, such as Lenovo, Dell, Compaq and NCR Corporation. These positions helped to cultivate the tech-driven and innovation-forward mindset which has made Chris integral to the ongoing growth of Cinch.

An art lover, Chris serves on the board of trustees for the Walker Art Center in Minneapolis, MN, one of the leading multi-discipline contemporary art museums in the world.

Andrea Kane
Andrea Kane Chief Human
Resources Officer

Andrea fosters a highly engaged culture, improves our talent and creates an all-around great place to work.

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Andrea Kane
Andrea Kane Chief Human
Resources Officer

Andrea focuses on enhancing culture while overseeing talent management, training and development and internal communication strategies.

Throughout her career, Andrea has held senior-level roles with well-known national brands, including AutoTrader Group, General Electric Company/NBC, Belkin International, Inc. and ADT. Throughout these previous positions, she gained considerable experience guiding companies through cultural and digital transformations while developing a passion for delivering creative and innovative talent solutions to bolster the company’s ability to attract, develop and retain great people.

Andrea received her Bachelor of Science degree in industrial and labor relations from Cornell University.

Chris White
Chris White Senior Vice President
of Marketing and Product

Chris brings more than 24 years of experience in transforming brands and elevating the customer experience.

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Chris White
Chris White Senior Vice President
of Marketing and Product

Chris leads all marketing initiatives, including corporate brand identity, external communications and online and offline direct response efforts.

A leading force in Cinch’s recent rebranding, Chris focuses on broadening distribution and product innovation in order to appeal to a wider range of consumer needs.

Chris has more than 24 years of experience transforming brands and elevating the customer experience for some of the top organizations in the country, such as Expedia and Motorola. Prior to joining Cinch, Chris was the vice president of retail products and client solutions at Asurion, where he managed the customer experience across 35 retailers — both online and in store — including leading brands like Walmart, Amazon and The Home Depot.

Chris received his Bachelor of Arts degree from Vanderbilt University and Master of Business Administration from the Kellogg School of Management at Northwestern University.

John Walsh
John Walsh General Counsel

John oversees all legal affairs, including contracting, litigation, regulatory compliance and risk management.

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John Walsh
John Walsh General Counsel

John oversees legal affairs, including contracting, litigations, regulatory compliance and risk management.

Previously, John was the general counsel and corporate secretary for Automotive Management Services, Inc., an automotive dealership management company, and has more than 20 years of experience in legal and corporate arenas.

John earned his Juris Doctor degree from Nova Southeastern University School of Law. He also serves as a coach for boys' youth hockey with the Florida Panther Development League.