who is olive®
olive.com takes transparency seriously, and as a customer-informed product provider, seeks to offer the best coverage for car owners. olive.com’s products, customer service, and reputation for excellence have earned it an A+ rating with the Better Business Bureau (BBB) and partnerships with leading insurance companies and globally recognized brands. With no inspection or waiting period, and plans for every budget, olive.com is in the business of helping people live life covered. PayLink Direct, the payment services division of olive.com, is one of the largest financial service providers of payment plan programs and transaction processing. It is a leading financial services company that specializes in providing interest-free payment plans for the purchase of service contracts for vehicles, RVs, homes, commercial trucks, and other products. Since the company’s inception in 2006, PayLink’s high-performing infrastructure has processed four million service contracts and originated $11 billion in receivables.
Founder and CEO, PayLink Direct and olive.com
Rebecca Howard is Founder and CEO of PayLink Direct and olive.com, affiliated businesses and leaders in payment services and online vehicle protection plans, headquartered in Chicago, IL and serving the US and Canada. Rebecca brings with her 22 years of experience and leadership in the vehicle protection plan industry.
In 2006, Rebecca founded PayLink Direct, and under her leadership, the company has secured the largest market share in payment services. PayLink Direct has a 15-year track record of profitability and has processed more than four million service contracts – over $11 billion of originated receivables – since the company’s inception.
In 2019, Rebecca launched olive.com, a digital vehicle protection plan platform built to give consumers peace of mind. Olive.com lets consumers buy direct, with no pressure, the way they want to buy, giving them an assortment of coverage and deductible options that are convenient and fit their budget. Olive.com’s digital platform has created a wave of new consumer buyers to the vehicle protection plan market, with over 59% of its customers being first-time buyers.
Prior to founding PayLink Direct and Olive.com, Rebecca led the growth and development of the vehicle service contract financing business for Mepco Insurance Premium Financing. She oversaw the company’s sales, marketing and operations functions.
Rebecca holds a Bachelor’s Degree in Commerce and Business Administration from the University of Michigan’s School of Business and resides in Chicago with her husband and two children.
President and COO, PayLink Direct and olive.com
Justin Thomas is President and Chief Operating Officer of PayLink Direct and olive.com, affiliated businesses and leaders in payment services and online vehicle protection plans, headquartered in Chicago, IL and serving the US and Canada. Since he joined in 2019, Justin has been focused primarily on strategic execution and growth for the companies.
Justin is a protection plan industry veteran, having spent over 18 years working for some of the largest providers and insurers in the world. Additionally, Justin has experience across a variety of consumer product segments and has successfully scaled multiple businesses and divisions throughout his career.
Before his current role, Justin was the President of Global Financial Services & U.S. Automotive National Accounts at Assurant (AIZ). Prior to this, he held various positions at The Warranty Group from 2007 to 2018, most recently serving as Executive Vice President, TWG Specialty Solutions.
Justin received a Bachelor of Arts in Communications with a dual minor in Marketing and Management from DePaul University.
Chief Financial Officer, PayLink Direct and olive.com
Armon Withey is Chief Financial Officer of PayLink Direct and olive.com, affiliated businesses and leaders in payment services and online vehicle protection plans, headquartered in Chicago, IL and serving the US and Canada. Armon is responsible for all financial functions, while also maintaining the company’s banking relationships and supervising the company’s operations team.
Armon brings over 25 years of financial experience to the companies. He has been with PayLink Direct and olive.com since 2008, first joining as VP of Accounting and Controller before becoming CFO in 2014.
Prior to this, Armon was a director of finance for Level 3 Communications, a multinational telecom and internet service provider, from 2006 to 2008. Armon previously served in leadership roles on the accounting team of Looking Glass Networks, a start-up telecom service provider, prior to its acquisition by Level 3 in 2006.
Armon has a Bachelor of Science in Accountancy from the University of Illinois and passed the CPA exam in the State of Illinois.
Chief Marketing Officer, olive.com
Paul Sherman is Chief Marketing Officer of olive.com. He leads all areas of the firm’s marketing strategy, from brand and creative to alliances and affiliate marketing, as well as the Auto OEM Marketing Services division.
Paul is an entrepreneurial-minded executive who has spent most of his 20-year career in the technology and retail sectors, at both public and privately held companies worldwide, maximizing brand awareness, market potential, competitive positioning to boost revenue through innovation.
Previously, he held leadership roles at SPX, Comcast, Gift Certificates.com (a previous Marlin Equities portfolio company) and Camping World. Paul has overseen global marketing budgets ranging from $5MM to over $100MM.
He has served on the board for Habitat for Humanity starting in 2013, and still helps this organization succeed through fundraising.
Paul has a BA in Business Administration from Purdue University.
Chief Information Officer, PayLink Direct and olive.com
Brett Beckerman is Chief Information Officer of PayLink Direct and olive.com, affiliated businesses and leaders in payment services and online vehicle protection plans, headquartered in Chicago, IL and serving the US and Canada. Brett oversees all technology behind PayLink Direct’s payment services and online vehicle protection plans for olive.com.
Since joining the company as CIO in 2008, Brett has been a visionary leader for using technology to satisfy both consumer and internal needs.
Brett has nearly 30 years of leadership experience serving in senior technology roles, predominantly in the financial services industry. Brett has created technology departments from the ground up with various organizations, prior experience in bringing organizations public, has instituted various internal compliance regulations to conform to PCI, SOC, SOX, etc., and has gone through due diligence, and M&A experience to combine the technology footprint of multiple entities into one. Prior to this, Brett was Vice President of Technology at Dovenmuehle Mortgage, where he was responsible for all technology for the mortgage loan sub-servicer and created a technology vision to provide enhanced services to his client base. Brett has also spent a number of years within the sub-prime auto lending industry creating customized proprietary, and hybrid, based payment processing and credit scoring application solutions.
Brett holds a Bachelor of Business Administration in Management Information Systems from California State University, Long Beach.
Chief Technology Officer, olive.com
Peter Dupre is Chief Technology Officer at olive.com. He oversees the customer experience and technical infrastructure to support all aspects of the customer experience. He has held this position since May 2020.
Peter has been a technologist and entrepreneur for over 35 years and has held several C-level positions at private and public companies. He has launched multiple startups in the technology space, most recently founding higher education software provider Jazz, Inc. in 2018 and business network services provider CloudPath in 2015.
He also developed machine learning systems to predict bond prices and other financial trends in the late 1980s and early 1990s.
Peter attended the AT&T school at MIT.
Executive Vice President of Customer Success, PayLink Direct and olive.com
Christine Galatte is Executive Vice President of Customer Success of PayLink Direct and olive.com, affiliated businesses and leaders in payment services and online vehicle protection plans, headquartered in Chicago, IL and serving the US and Canada. In this role, Christine creates an industry leading customer experience by enhancing operational processes and seeking strategic solutions that support the businesses’ products and services.
Since joining in 2007, Christine has overseen contact center activities for customer service, client service and dealer service, including client onboarding, ongoing relationship management, all customer communication channels and customer retention.
Christine brings over 30 years of operational and strategic experience to the business. Previously, she was Director of Bank Operations and Payment Strategy for Discover Financial Services.
Christine has a Bachelor of Science in Finance from Northern Illinois University and a Master of Science in Communication and Media Studies from Northwestern University.
Vice President, General Counsel and Corporate Secretary of PayLink Direct and Olive.com
Kevin Hovis is Vice President, General Counsel and Corporate Secretary of PayLink Direct and olive.com, affiliated businesses and leaders in payment services and online vehicle protection plans, headquartered in Chicago, IL and serving the US and Canada. Since joining the company in 2010, Kevin has managed all legal matters, including drafting and negotiating all terms and conditions of contracts with administrators, sellers and insurers, and directing company compliance with state and federal consumer finance and marketing statutes and regulations.
Kevin has over 20 years of experience as a practicing attorney, including more than 13 years in the role of General Counsel for both public and private entities.
Prior to joining PayLink Direct and Olive.com, Kevin was the General Counsel for the Governor’s Office of Management and Budget for the State of Illinois, where he was Chief Legal and Regulatory Counsel for the agency responsible for the formulation and implementation of statewide fiscal, budgetary and managerial policy. Previously, Kevin was in private practice at Schiff Hardin LLP where he represented clients in the defense of nationwide consumer class actions and complex commercial disputes.
Kevin holds a Bachelor of Arts in English from Indiana University Bloomington and a Juris Doctor, Cum Laude, from the University of Illinois College of Law, and is licensed to practice law in the State of Illinois.