Leadership

Executive Team

Terrence McCrossan

Chief Executive Officer

Terrence McCrossan

Chief Executive Officer

Terrence joined Oversight as CEO in July 2018, bringing more than 25 years of payment industry, SaaS technology, and executive leadership experience to his role. As CEO, he focuses on driving Oversight to the next level as a leading provider of artificial  intelligence-powered financial risk mitigation and compliance monitoring software solutions for Fortune 1000 business and government clients.

 

Prior to Oversight, Terrence served as Senior Vice President and General Manager for Comdata, a leading payments and fleet management division of FLEETCOR (FLT). Before Comdata, he spent 10 years in executive marketing, strategy and operating roles with ADP, most recently serving as Division Vice President and General Manager of ADP Vantage HCM, a leading SaaS solution for large enterprises. Earlier in his career, he held sales and marketing positions at MCI and Internet Security Systems. Terrence has an MBA from Wake Forest University and a B.A. in Political Science from Villanova University.

Geoff Brannon

Chief Financial Officer

Geoff Brannon

Chief Financial Officer

Geoff Brannon oversees the Finance and Accounting functions at Oversight Systems to provide strong daily operational support of the business and to enable strategic decisions for growth and investment opportunities. Geoff brings twenty years of experience leading financial planning & analysis, treasury, accounting, M&A, compliance, and financial reporting functions in global technology organizations. Throughout his career, Geoff has focused on operational excellence in firms with significant complexity offering an array of solutions including software, hardware, and professional services.

 

Prior to joining Oversight, Geoff worked as Division CFO of NCR Corporation’s hospitality business. He joined NCR by way of its acquisition of Radiant Systems in 2011, where he was Corporate Controller after a successful progression of various management roles in its accounting function. Geoff also worked at LSI Corporation, which has since been acquired by Broadcom Limited, and started his career in the assurance practice of KPMG. Geoff holds a BA in Accounting and an MBA in Finance from Georgia State University.

Mike Rivers

Chief Technology Officer

Mike Rivers

Chief Technology Officer

Mike Rivers drives the Technology Development, Security, and IT Operation groups at Oversight Systems to ensure seamless integration and high performance for its enterprise customers. His experience spans more than twenty years of software product development, security strategy and operational excellence in financial services technology. He is a strong leader with proven success in building technology products at the intersection of SaaS, security, analytics and compliance.

 

Throughout his career, Mike has helped early stage and high growth technology companies scale for success. Prior to joining Oversight, Mike held the position of CTO for Paymetric, a leading cloud-based payments security company. He has also been a senior executive at multiple financial and software service companies including TransComm, Thoughtmill, Xpanxion and Ingenico. Mike has a Bachelor of Science degree in Management Information Systems from the University of Texas.

Manish Singh

Chief Operating Officer

Manish Singh

Chief Operating Officer

Manish Singh is an expert at providing solutions that leverage advanced analytics to automate audit and risk management processes and streamline business operations. His background includes expertise in multiple areas of operations from product strategy and sales, to client-facing consulting, delivery, and account management. Manish joined the Oversight team in 2008 and served in various leadership roles prior to his appointment as Oversight’s Chief Operating Officer.

 

Prior to joining the Oversight team, Manish worked at PRGX, a provider of recovery audit services, where he managed the audit data flow process from client data acquisition to audit data delivery. At PRGX, Manish led initiatives to drive incremental revenue growth by leveraging clients' unstructured data to uncover hidden profit opportunities. Manish graduated as an honor’s scholar with a Bachelor of Science degree in computer science from Kennesaw State University, and he holds an MBA from Emory University’s Goizueta School of Business.

Jessica Kirk

VP, Marketing

Jessica Kirk

VP, Marketing

Jessica Kirk has served as head of marketing at Oversight Systems since 2013. In her role as Vice President of Marketing, Jessica leads development and execution of marketing strategy, branding, communications, demand generation, events, digital marketing, and public relations.

 

Prior to joining Oversight, Jessica held marketing leadership roles with several B2B software organizations. At RedPrairie (now JDA Software), she was responsible for driving demand and delivering top line growth through the execution of corporate events and digital programs. At Bomgar, she implemented best practice processes to improve ability to measure marketing effectiveness and directed all marketing events. At TerraGo Technologies, Jessica was a marketing manager responsible for overseeing corporate event marketing, advertising, and public relations. Jessica holds a bachelor’s degree in communication studies from the University of North Carolina at Charlotte.

Terri Jones

VP, Human Resources

Terri Jones

VP, Human Resources

Terri Jones has served as Vice President of Human Resources (HR) at Oversight Systems since March 2009. Terri is responsible for leading HR strategy and building a sustainable corporate culture that accelerates Oversight’s growth, performance, leadership, and talent recruitment and retention.

 

Terri brings more than 20 years of human resources leadership experience to her position. Prior to joining Oversight, Terri was Vice President of Human Resources at Internet Security Systems (ISS) for 10 years - from start-up through IPO and the sale of the company to IBM. At ISS Terri had global responsible for leading Human Resources in 26 countries. Her responsibilities included talent management, recruitment and retention as well as all other areas of Human Resources. Terri holds a bachelor’s degree in Management Information Systems from The University of Georgia. Terri is passionate about wildlife preservation and in her spare time focuses on raising money to fight poaching in Africa.

Board of Directors

Tim McAdam

Tim McAdam

Tim joined TCV in 2010 and focuses on investments in the enterprise software, security, and tech-enabled services markets. His current investments include Alarm.com (NASDAQ: ALRM), FinancialForce, Silver Peak, and Vectra. His prior investments include Avalara (NYSE: AVLR), Rapid7 (NASDAQ: RPD), Splunk (NASDAQ: SPLK) and TOA Technologies (acquired by Oracle).

 

Tim was previously a partner at Trinity Ventures, a leading early- to mid-stage venture capital firm, where he focused on investments in the software and security sectors. Prior to Trinity, Tim was a vice president at GTCR in Chicago. He started his career in the early 1990s at TA Associates in Boston.

 

Tim received his M.B.A. from the Stanford Graduate School of Business and graduated with a B.A. in Classical Archaeology from Dartmouth College.

Gal Peleg

Gal Peleg

Gal joined TCV in 2018 and focuses on investments in the software and tech-enabled services sectors. He also supports TCV’s investment in Rave Mobile Safety.

 

Prior to TCV, Gal was a Vice President at New Mountain Capital (NMC), where he evaluated and executed investments across the technology sector. Prior to NMC, Gal spent several years with McKinsey & Company, where he served technology, private equity, and public sector clients.

 

Gal received a B.S. in Computer Science from Brown University.

 

Hollie Haynes

Hollie Haynes

Hollie Moore Haynes is the Managing Partner of Luminate Capital Partners and is based in San Francisco, CA. Prior to founding Luminate, Hollie focused on software private equity investing at Silver Lake. Earlier in her career she worked in private equity at Hellman & Friedman and in investment banking at Morgan Stanley & Co. She graduated from Harvard University with an A.B. in Economics and received an M.B.A. from the Stanford University Graduate School of Business.

Scott Kingsfield

Scott Kingsfield

Scott Kingsfield is an Operating Partner at Luminate Capital Partners and is based in Atlanta, GA. Prior to Luminate, Scott served as President of the Retail Division at NCR. Before joining NCR he held multiple executive roles at Radiant Systems, which was known as the leading provider of technology solutions to the retail and hospitality industry. Scott began his career as a management consultant with Arthur Andersen and Price Waterhouse. Scott received his B.A. in Finance from Georgia State University.