Executive Career

A career built across entrepreneurship, global scale, security, transformation, and technology-enabled growth.

Stephen's career has progressed from co-founding and scaling a telecommunications business to leading global technology, cybersecurity, compliance, data, and AI organizations. Each role expanded the operating scope while reinforcing the same leadership pattern: build strong foundations, reduce risk, scale responsibly, and connect technology decisions to business performance.

Entrepreneur & CIO → North American IT & Security Leader → Global Technology & Security Executive → CIO & Acting CISO → CTO & Acting CISO

Chief Technology Officer & Acting Chief Information Security Officer · 2022–Present

Stephen joined Peak Support to establish the CIO function during a period of rapid growth, with responsibility for technology, security, compliance, data, and the digital workplace. As the enterprise foundation matured, the role evolved toward CTO ownership of platforms, AI, analytics, automation, and client-facing technology services while retaining Acting CISO accountability.

  • Built the enterprise technology, security, and compliance operating model required to support regulated growth, achieving ISO/IEC 27002-aligned controls, PCI DSS Level 1, SOC 2 Type II, and HIPAA.
  • Modernized data and analytics around Microsoft Fabric, Power BI, and AI-enabled reporting.
  • Led technology, cybersecurity, compliance, and data diligence supporting Peak Support's acquisition by Ubiquity — and, post-close, paused a planned independent ISO 27001 certification to align with Ubiquity's existing 27001 program rather than duplicate the effort.

Global Vice President, Enterprise Infrastructure & Security · 2014–2021

Stephen progressed from Director of Technology Infrastructure to Global Vice President, leading enterprise infrastructure, security, compliance, architecture, and operations across a workforce of more than 25,000 employees.

  • When COVID-19 forced an emergency shift to remote work, led the rapid work-at-home transformation from zero to 3,000 agents in 45 days and more than 10,000 within four months, without breaking compliance.
  • Built the enterprise security and compliance environment across PCI DSS, HIPAA, HiTRUST, SOC 1, and SOC 2 — including completing a stalled PCI DSS certification within 30 days of starting.
  • Led technology and security integration for four acquisitions (TLK Group, Corporate Call Center Inc., USA800, DeviceBits), integrating roughly 6,000 employees, and delivered more than $2.5M in annualized infrastructure and carrier savings.

Director of IT & Security, North America · 2010–2014

Stephen led technology and security across North American contact center, eCommerce, healthcare, logistics, and supply-chain operations supporting more than 5,000 users across multiple countries.

  • Delivered ISO/IEC 27001 certification and PCI DSS Level 1 certification in 6 months, start to finish, against a client-imposed deadline to preserve a major Microsoft services contract.
  • Delivered eight major contact-center site builds across the United States, Mexico, and the Philippines.
  • Delivered $1M+ in annual telecom and network savings through vendor optimization.

Co-Founder, Chief Information Officer & Executive Board Member · 1999–2020

Stephen co-founded the business as a paging company, helped move it into eCommerce through Beepers.com, and supported its growth into a regional wireless retail organization.

  • Built the technology platform supporting growth from startup to 65 retail locations at peak.
  • Served as CIO and executive board member through more than two decades of company growth.
  • Developed the operator's perspective that shaped his later enterprise leadership roles.

A consistent progression of scope.

Across each stage of his career, Stephen's responsibilities expanded, but the operating pattern remained consistent: establish discipline, simplify platforms, strengthen security and governance, build capable teams, and position technology as a contributor to growth and enterprise value.

Explore Executive Impact