Meet Digital.ai Leadership
We are a globally distributed team with a mission to unlock endless digital possibilities by harmonizing the delivery of software. We help our customers along their journey to digital transformation.
Leadership Team
Derek Holt
Chief Executive Officer
Derek Holt
Chief Executive Officer
Derek Holt is CEO of Digital.ai and a noted voice on how AI is transforming both software delivery and enterprise operating models.
He leads an organization that is driving the shift from coding-centric AI to agentic AI applied across the full business process of software development and delivery—where the real constraints to speed, quality, and risk exist. Under his leadership, Digital.ai is helping Global 2000 organizations apply AI upstream in planning and downstream in security, testing, and DevOps, enabling faster, more secure, and more predictable software delivery. The company is trusted by 53% of the Fortune 100.
At the same time, Derek and his leadership team are spearheading Digital.ai’s own evolution into an AI-first enterprise—demonstrating how private equity-backed software companies can embed AI across product innovation, go-to-market, operations, and decision-making to drive measurable business outcomes.
Derek brings more than 20 years of experience leading both large enterprise and startup technology companies. He joined Digital.ai after serving as President and COO of K4Connect, a venture-backed IoT software company. Earlier in his career, Derek was a member of the founding executive team at Startup America Partnership, a public-private initiative with the White House focused on accelerating entrepreneurship and regional startup ecosystems. He began his career at IBM Software Group, where he held a range of technical and business leadership roles across development, strategy, services, and sales, helping Global 5000 organizations drive agility and business value through digital and AI transformation.
Derek holds a BS in Computer Science from The Pennsylvania State University and an MBA from Duke University’s Fuqua School of Business, where he was a Fuqua Scholar..
X
Nicholas Grabowski
Chief Product Officer
Nicholas Grabowski
Chief Product Officer
Nicholas Grabowski is the Chief Product Officer at Digital.ai. He brings 30 years of experience in building Technology. In his role as CPO at Digital.ai, Nick will drive product strategy and delivery and support branding and marketing efforts. Nick has extensive experience designing and building technology as well as operating startups and public companies. Before joining Digital.ai Nick was CEO of Flow, Inc., CTO at ForgeGlobal and CTO/CPO at Sharespost. Nick also ran the R&D and Centralized Architecture functions for Charles Schwab. Nick helped ForgeGlobal to a $2B IPO in 2022 and built the technology stack that helped Ebates.com sell for $1B in 2010.
X
Patricia Prince-Taggart
General Counsel
Patricia Prince-Taggart
General Counsel
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.
X
Randall Robinson
Chief Financial Officer
Randall Robinson
Chief Financial Officer
Randall is the Chief Financial Officer at Digital.ai. Randall brings a proven track record of success in private equity-backed software companies, with deep experience in SaaS business models and scaling organizations globally. Throughout his career, Randall has guided multiple companies through key phases of growth, while delivering strong results for customers, employees, and investors alike. Most recently, as CFO of ProfitSolv, Randall lead the global finance, accounting, M&A, revenue operations and strategic planning functions, which led to accelerated growth and a successful outcome. Randall brings a strong foundation across all key finance roles and prides himself in working with and developing great teams with a collaborative leadership approach and a commitment to transparency.
X
Keith Stewart
Chief Customer Officer
Keith Stewart
Chief Customer Officer
Keith Stewart is the Chief Customer Officer at Digital.ai and is responsible for customer facing teams, including customer support, sales engineers, and professional services. Keith brings to Digital.ai over two decades of leadership experience across large multinational organizations and venture backed early-stage startups. Prior to joining Digital.ai, Keith was Chief Revenue Officer at Flow where he led revenue and growth teams to help customers achieve their digital transformation goals. Keith also held leadership roles at K4Connect and Site 1001. Keith had an impressive 12+ years at IBM serving in several international roles including, Global Solution Sales Leader for Watson IoT and European Business Unit Executive for Smarter Infrastructure.
X
Wing To
Chief Technology Officer
Wing To
Chief Technology Officer
As General Manager of the Intelligent DevOps business unit at Digital.ai, Wing brings more than 20 years of experience delivering world class software products and services, driving innovation, and leading successful product and engineering teams. In his current role Wing leads a global business unit with teams across seven major global labs. Wing joined Digital.ai after serving 14 years at IBM, in VP roles across strategy, product management and development where he delivered software solutions in agile transformation, DevOps, system and application management, IT Operations and IT Service Management. Prior to IBM, Wing was the SVP for Products for Micromuse, delivering market leading software in IT Operations and Network Management to the top Global 2000 Enterprises. Wing holds a PhD in Computer Science from Imperial College, London, UK.
X
Board of Directors
Stephen Elop
Executive Chairman
Stephen Elop
Executive Chairman
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. Most recently Stephen served as CEO at Digital.ai and before that he was CEO of APiJet after serving as Group Executive of Technology, Innovation, and Startegy 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.
X
Art Heidrich
Board Member
Art Heidrich
Board Member
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.
X
Derek Holt
Board Member
Derek Holt
Chief Executive Officer
As CEO of Digital.ai, Derek brings more than 20 years of experience leading large enterprise and startup technology companies with a consistent focus on the digital transformation. Prior to being promoted to CEO, Derek was General Manager of DevOps business unit. 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.
X
Nehal Raj
Board Member
Nehal Raj
Board Member
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.
X
Angela Tucci
Board Member
Angela Tucci
Board Member
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.
X