Leadership team

Meet the Digital.ai leadership team

Stephen Elop
Stephen Elop
Chief Executive Officer
Stephen Elop

Stephen Elop is a seasoned leader with more than 20 years of experience spanning enterprise software and smart devices. Throughout his career, he has participated first-hand in the accelerating trends of digital transformation, and the changes of methodologies and techniques that are making that possible. Prior to his current role, Stephen served as CEO of APiJET, and before that, as Group Executive of Technology, Innovation, and Strategy at Telstra. Earlier in his career, he served in multiple leadership roles at Microsoft, and at Nokia where he served as the President and CEO. Stephen has also held executive roles at Juniper Networks, Adobe Systems, and Macromedia.
 

Jeff Moloughney
Jeff Moloughney
Chief Marketing Officer
Jeff Moloughney
Jeff is a seasoned marketing executive helping drive go to market strategies across marketing, product and sales teams for SaaS, growth and traditional software organizations. Jeff has two decades of experience in the business and software application market holding roles across marketing, sales, product and business development. He recently joined us from ServiceNow where he was the head of product and solutions marketing for numerous technology solutions and was accountable for aligning marketing’s strategy and execution to business objectives. Prior to ServiceNow, he was responsible for marketing CA Technologies Agile Management and Portfolio Management solutions, and he has held marketing and product leadership roles for BMC, FrontRange Solutions (currently Ivanti) and Oracle.
Bruce Chesebrough
Bruce Chesebrough
Chief Revenue Officer
Bruce Chesebrough

Bruce Chesebrough joins Digital.ai from TPG Capital where he was on the Field Operations team. Bruce specializes in sales effectiveness and has worked in more than 100 industries including: software, ecommerce, insurance, publishing, plastics, defense, building materials, engineering, chemicals, construction, medical equipment, IT infrastructure, distribution, third party logistics, and precision machining and fabrication. Bruce's recent TPG software engagements include serving as Acting Chief Revenue Officer at Ellucian, Acting CRO at Footballco, and Sales Operations advisor at Transporeon. Prior to joining TPG, Bruce held positions as Managing Director of the Revenue Enhancement practice at Alvarez and Marsal and Chief Revenue Officer at Corbis Corporation. Bruce holds a BA in economics from Amherst College and an MBA from Harvard Business School.

Prasenjit Dasgupta
Prasenjit Dasgupta
Chief Financial Officer
Prasenjit Dasgupta

Prasenjit Dasgupta is the chief financial officer at Digital.ai and is responsible for leading the company’s worldwide finance organization. Prasenjit brings to Digital.ai more than 20 years of leadership roles with a proven track record in technology, where he was responsible for leading global teams supporting multi-billion-dollar operations within a dynamic market environment. He previously served as the Corporate Vice President and CFO of the Software & Services group at Motorola Solutions. Prior to Motorola, Prasenjit spent nearly 14 years at Microsoft in the Finance Organization where he held positions of increasing responsibility, lastly as Senior Director, FP&A, pricing and analytics in the Experiences and Devices group.  Earlier in his career, Prasenjit worked for the Boston Consulting Group in Germany and T-Mobile in the United Kingdom.

Prasenjit graduated with a Bachelors in Electrical Engineering from the Delhi College of Engineering and has an MBA from the Indian Institute of Management, Calcutta.

John Allessio
John Allessio
Chief Customer Officer
John Allessio

John Allessio joins Digital.ai from his previous role as Executive Vice President and Chief Customer Office at PROS. John excels in pre-sales engineering, as well as all post-sales functions including professional services, customer support, training, and ultimately customer success. Prior to his time at PROS, John was Senior Vice President and General Manager of Global Services at Red Hat, responsible for consulting services, training and certification services, technical and business partner enablement, and pre-sales solution architecture programs. John had an impressive 27+ year career with IBM serving in several senior roles, including, Vice President of Software Services, Support, and Success - Industry Cloud Solutions, and leading the SaaS Operations and Client Success organization - a team of software consultants and support engineers in 35+ countries with a goal of Industry Solutions software client success.

Patricia Prince-Taggart
Patricia Prince-Taggart
General Counsel
Patricia Prince-Taggart

As chief general counsel with Digital.ai, Patricia Prince-Taggart is responsible for the firm’s global legal team. With more than 25 years of legal experience, Pati previously served as general counsel and chief of staff at Cognitive Scale Inc.; as SVP, chief counsel at CA Technologies; and as general counsel for start-ups in Austin, Texas. During her career, Pati has been responsible for all aspects of legal work including corporate, IP and products, transactional, employment, ethics, and compliance. In 2016, Pati received the Global Counsel Award, general commercial category, in recognition of achievements as in-house counsel. Pati is a graduate of the Pace University School of Law.

Aviad Arviv
Aviad Arviv
General Manager, Security
Aviad Arviv

As General Manager of Security, Aviad Arviv brings more than 20 years of experience in global operations and business development to Digital.ai. He joined Digital.ai following its acquisition of Experitest, a leading provider of mobile and web application testing solutions, where he served as Chief Revenue Officer. During his career, Aviad has been instrumental in overseeing revenue growth in sectors including DevOps, Cyber Security, and Media. Previously, he held senior leadership roles at companies including NorthBit Cyber Security, where he served as COO, and Perion, where he was VP of Monetization. 

Derek Holt
Derek Holt
General Manager, Agile and DevOps
Derek Holt

As General Manager of Agile and DevOps, Derek brings nearly 20 years of experience leading large enterprise and startup technology companies with a consistent focus on the digital transformation. Derek joined Digital.ai after serving as President & COO of K4Connect, a venture backed IoT software company focused on bringing digital solutions to empower older adults and individuals living with disabilities. Prior to K4Connect, Derek was a member of the founding executive team at Startup America Partnership, a public-private partnership with the White House focused on accelerating entrepreneurship and regional startup ecosystems. He began his career at IBM Rational where he served in various technical and business leadership roles across development, strategy, services, and sales with a core focus on helping Global 5000 companies drive business value and agility through agile digital transformation.

Board members

Nehal Raj

Nehal Raj is a Partner at TPG based in San Francisco. He co-leads the firm’s investment activities in software and enterprise technology across its private equity platforms (TPG Capital, TPG Tech Adjacencies, TPG Growth, and The Rise Fund). Prior to joining TPG in 2006, Nehal was an investor at Francisco Partners. Previously, he worked in the Mergers, Acquisitions, and Restructurings Department of Morgan Stanley. He received an AB in Economics and MS in Industrial Engineering from Stanford University (Phi Beta Kappa) and an MBA from Harvard Business School (Baker Scholar). Nehal currently serves on the board of the following TPG investments: C3.ai, Digital.ai, Kaseya, Noodle.ai, Sutherland Global Services, WellSky, and Wind River Systems. He is also closely involved with the firm’s investments in Checkmarx and Sonatype. Nehal was previously a director of a number of TPG investments prior to their successful exits, including: CCC Information Services (acquired by Advent International), IQVIA (NYSE: IQV), Intergraph (acquired by Hexagon AB), and Zscaler (NASDAQ: ZS). Nehal serves on the Board of Trustees of San Francisco Day School and the Advisory Board of Breakthrough San Francisco.

Art Heidrich
Art Heidrich
Art Heidrich

Art Heidrich focuses on technology investments across TPG’s private equity platforms (TPG Capital, TPG Growth, and The Rise Fund). He has been or is currently involved with TPG’s investments in Advent Software, C3 IoT, Eze Software, IMS Health, RefleXion Medical, Sonatype, Vertafore, and WellSky. Prior to joining TPG, he worked in the Technology group at Morgan Stanley, where he advised on and executed M&A and corporate finance transactions.
 

Stephen Elop
Stephen Elop
Stephen Elop

Stephen Elop is a seasoned leader with more than 20 years of experience spanning enterprise software and smart devices. Throughout his career, he has participated first-hand in the accelerating trends of digital transformation, and the changes of methodologies and techniques that are making that possible. Prior to his current role, Stephen served as CEO of APiJET, and before that, as Group Executive of Technology, Innovation, and Strategy at Telstra. Earlier in his career, he served in multiple leadership roles at Microsoft, and at Nokia where he served as the President and CEO. Stephen has also held executive roles at Juniper Networks, Adobe Systems, and Macromedia.
 

Angela Tucci
Angela Tucci
Angela Tucci

Angela Tucci has more than 20 years of experience leading and managing business operations, integrations, and strategic growth initiatives at enterprise technology companies. Most recently, she served as CEO of Apto. Prior to Apto, she served as General Manager of the Agile Management Unit of CA Technologies, and before that, as Chief Revenue Officer of Rally Software and Chief Strategy Officer of Symantec. Presently, Angela is Chairperson for the Anita Borg Institute for Women and Technology, Director of Progress Software (NASDAQ: PRGS) and Chief Operating Officer for Uplight, Inc.
 

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