Leadership Team

As Chief Executive Officer and Executive Chair, as well as the Chairman of Skillsoft’s Board of Directors, Ron has a wealth of executive leadership and operational experience in the technology and software industries. He is also currently Chairman of the Ansys Board of Directors, on which he has served since 2012.  
 
Ron brings decades of experience leading technology companies to the next stage of growth and innovation. Before  Skillsoft, he served as President and Chief Executive Officer of Indigo Ag, a leader in sustainable agriculture solutions. Prior, Ron was Executive Chair of Skillsoft and Executive Partner at Flagship Pioneering, the founding company of Indigo Ag, from 2018 to 2021. Earlier in his career, Ron served as President and Chief Executive Officer at Intralinks, Inc., and President and Chief Executive Officer of Novell, Inc. He also spent several years in venture capital directly assisting companies at each stage of development, from early ideation through growth phases, while serving as a board member. He started his career at IBM and served in many executive positions over approximately a 16-year period.   
 
Ron holds a Bachelor of Science from Boston College.

As Chief Financial Officer, Ron oversees Skillsoft's finance and legal functions, working closely with the CEO and senior leadership team to drive business strategy, performance measurement, and operating plan execution. 

Ron Kisling is a seasoned public-company technology CFO, having served six times in the CFO role, with over 15 years of CFO experience and more than 40 years in finance. He has deep expertise in M&A, capital markets, and strategic transitions. During his tenure as CFO at Fitbit, the company achieved $1.5B in annual revenue and completed its $2.1B acquisition by Google. He later served as CFO of Fastly, guiding the company through a period of significant growth and complexity at over $600M in revenue.

Ron has direct experience managing capital structure in public technology companies, including debt repurchase strategies to reduce leverage and refinancing to strengthen balance sheet flexibility. His background reflects strong financial leadership during periods of transformation and change, with a foundation in public accounting from PwC.

As Chief Marketing Officer, Raianne oversees Skillsoft’s global marketing strategy, with a focus on driving demand and strengthening brand awareness among organizations and learners navigating their talent transformation journeys. 
 
Raianne brings more than two decades of experience leading brand development and accelerating growth for global technology companies. Before joining Skillsoft, she served as Executive Vice President and Chief Marketing Officer at Yext, where she led all aspects of marketing including corporate brand strategy and communications, product marketing, demand generation, operations, and business development. Prior, Raianne was Vice President of Marketing at Elastic, an AI search platform, and Head of Americas Marketing at Amazon Web Services. Earlier in her career, she held senior marketing roles at high-growth companies including Juniper Networks, Tellabs, and 3Com.  
 
Raianne holds a Bachelor of Science in Business Management from Northern Illinois University.

As Chief Information Officer, Orla oversees Skillsoft’s technology strategy and execution, enterprise business solutions, infrastructure & operations, end user services, data governance, and engineering.  
 
Orla has extensive experience with technology and business transformation, mergers & acquisitions, and organizational change management. Before joining Skillsoft, she held IT leadership roles at National Grid, with accountability for the U.S. customer organization technology footprint, leading IT and digital organizational change management, and serving as Chief of Staff for the Chief Information & Digital Officer. Earlier in her career, she worked at ExxonMobil in the United Kingdom, France, and Belgium in both IT and business roles, as well as EMC in Massachusetts, where she demonstrated a successful track record fostering strong business partnerships, evolving the IT operating model, and leading the company’s largest transformation program to enable go-to-market strategies. As part of the Dell EMC merger, Orla led the IT integration for sales and marketing, before heading up Dell’s global IT marketing organization.  
 
Orla holds a Bachelor of Arts in International Marketing with French and German from Dublin City University, Ireland, and an Master of Science in IT from Stirling University, Scotland. 

As Chief Revenue Officer, Matthew oversees driving growth across Skillsoft’s business segments.  
 
Before joining Skillsoft, Matthew served as Vice President, Security Sales at IBM, where he was responsible for all security-related products and services. Prior, he was Vice President of IBM’s Integrated Security Business Unit – Asia Pacific, where he oversaw security software sales and services and was a member of the company’s regional Senior Leadership Team. In Matthew’s prior roles in Greater China for IBM, he was a member of the Global Technology Services leadership team, holding the positions of General Manager, Global Technology Services, Hong Kong, and Head of Client Management and Offerings. In these roles, he had country and regional P&L responsibility for all managed service clients, as well as technology solutioning, consulting, and go-to-market offerings. Earlier in his career, he was Vice President of Field Alliances for SAP America.  
 
Matthew holds a Bachelor of Science in Political Science from Rutgers College and a Master in Business Administration from the George Washington University. He holds a certification from IBM’s Harvard Business School Certification Program and is a graduate of IBM’s Master Deal Making program through the Wharton School of Business.

As Chief Transformation and Operations Officer, Jose is responsible for driving Skillsoft’s enterprise-wide transformation, building an integrated management system, and enabling seamless, end-to-end operations across the company. His expanded remit brings together Transformation, Operations, and IT—ensuring full alignment between process, systems, and strategy to accelerate execution, scalability, and business impact.

Jose brings over two decades of global leadership experience across public and private companies, having served in CEO, COO, CIO, President, and General Manager roles. His career spans startups, scale-ups, and global enterprises—where he has led organizations through growth, integration, and transformation. Prior to Skillsoft, he served as Senior Vice President of Business Transformation and Operations at PTC, where he led the company’s SaaS transition, major restructuring programs, and cross-functional operating model redesigns that improved productivity and profitability. Earlier, he held senior leadership roles at Simplivity, Intralinks, Novell, and Cambridge Technology Partners, guiding global operations, GTM alignment, and IT modernization across diverse technology and services portfolios.

Jose began his career in management consulting and has held CEO and Board positions for technology and services organizations across the Americas. Throughout his career, he has built a reputation for operational excellence, data-driven execution, and the ability to connect strategic vision with disciplined implementation.

Bilingual in English and Spanish, Jose holds a Bachelor of Computer Science in Computer Engineering from Universidad Simón Bolívar (Cum Laude) and completed MBA coursework at Universidad Metropolitana in Caracas, Venezuela.

Scott Semel serves as Skillsoft’s Interim Chief Legal Officer, overseeing the company’s global legal, security, compliance, and governance functions. In this role, Scott partners closely with the Executive Leadership Team to support Skillsoft’s strategic priorities while ensuring strong governance and risk management across the organization.

Scott brings deep experience leading legal functions at global technology companies. Prior to joining Skillsoft, he held senior legal leadership roles at EngageSmart, Carbonite, Intralinks, and Novell, and has supported numerous public company boards. Throughout his career, Scott has been known for helping organizations move quickly while maintaining the right legal, commercial, and governance frameworks.

A trusted business partner, Scott approaches decision-making with strong commercial awareness and balanced judgment, positioning legal as an enabler of strategy rather than a barrier to progress.

Scott holds a bachelor’s degree from Boston University.

Bernard (“Bernie”) Barbour serves as Skillsoft’s Chief Technology and Product Officer, where he leads the company’s global product and technology strategy, including Product and Engineering. 

Bernie is an experienced technology leader with deep expertise in AI, cloud platforms, enterprise SaaS, and scaling global engineering and product organizations. Before joining Skillsoft, he served as Chief Technology Officer at Indigo Agriculture, where he led initiatives to modernize core systems, enhance data capabilities, and support the company’s growth. Prior to Indigo, Bernie spent more than a decade at Cimpress, where he led a global platform organization of more than 700 team members and oversaw the development of content creation tools, design technologies, personalization engines, and large-scale transactional systems used across global markets.

Known for his builder’s mindset, Bernie brings a passion for solving complex problems, simplifying systems, and developing high-performing teams that deliver with clarity and purpose.

Bernie holds a bachelor’s degree in Mathematics and Computer Science from Providence College.