Stewart is a Senior Vice President with Mastek, leading the company‚Äôs go-to-market strategy and client-facing team for Healthcare, Life Sciences, and Medical Devices across North America. Before Mastek, Stewart was a General Manager with Wipro and responsible for Sales, Services, Operations, Finance, and account-based Strategy across a $50M+ global portfolio of Life Sciences and Medical Technology clients. In this role, he owned the P&L and led a diverse worldwide team of over 800 individuals providing professional services across IT Infrastructure, Applications, Engineering, Digital Transformation, and Pharmacovigilance. Previously, Stewart was a Global Client Partner with Wipro and led a multinational 400+ member team providing IT Infrastructure, Help Desk, Risk, and Security services for a strategic client.

In 2008, Stewart co-founded The Simage Network and was the VP of IT and Operations, CTO, and Board Member. While with Simage, Stewart led the product ideation, design, custom infrastructure build, security, and cloud support of their Digital Out of Home new media network across North America. Before this, he was a co-founder, principal consultant, and CEO of Aspen Consulting, a $20M Chicago-based IT services firm that placed 24th on the Inc. 500 list in 1998 and 227th in 1999. In addition to providing infrastructure consulting, Aspen specialized in Tivoli software sales and services. In 2003, Aspen was sold to Optimus Solutions, which SoftChoice later acquired. After the acquisition, Stewart focused on integrating, leading, and growing the professional services practices across both organizations.

Stewart’s other experience includes technical sales and engineering roles at IBM and Reuters. While with Reuters, he worked across Europe and the US, installing and managing implementations of trading systems at firms such as: UBS, Credit Suisse, ABN-AMRO, and HandelsBank NatWest. While with IBM, Stewart served clients across Healthcare Payers, Providers, and Life Sciences, including United Healthcare, HCSC, BCBS Minnesota, Regence, Mayo Clinic, NW Memorial Hospital, Astellas, Takeda, and Baxter.

Stewart has served on the Chicago Chapter of the Entrepreneurs’ Organization (EO) Board of Directors and has mentored other entrepreneurs throughout his career. Earlier in his career, he was named to The Business Ledger’s 40-Under-40 and was a Finalist for the Ernst and Young Entrepreneur of the Year Award. In addition, while a co-founder of Aspen Consulting, the organization was named to the Computer World – Emerging Companies to Watch in 2000 list and the Smart Reseller Top 100.

In 2009, while a co-founder at Simage, Stewart earned his Executive MBA from the Kellogg School of Management at Northwestern University. In addition, he attended the Owner / President Executive Education program at Harvard Business School. Stewart holds a Bachelor of Science in Computer Engineering from Iowa State University.

A proud father of four, Stewart lives in Wilmette, Illinois (just outside of Chicago) and enjoys cycling, hiking, running, cooking, and relaxing in Napa Valley.

Contact Stewart for these roles:

  • Chief Operating Officer
  • Board of Directors
  • Professional Services Delivery, Sales and Operations
  • Software Sales and Delivery
  • Operations and P&L Management
  • Pre-Sales and Sales Leadership
  • General Manager
  • Hands-on IT Management and Leadership
  • Interim or Full Time CxO
  • CIO, CTO for Entrepreneurial and Growth Stage Technology company
  • Strategic Advisor