Executive Counselor – Trusted Advisor to CIOs, Technology Leaders

Posted 5hrs ago

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Job Description

Executive Counselor advising CIOs and technology leaders across Canadian financial, insurance, professional services, and not-for-profit organizations. Applying executive judgment, research, analytics, and advisory expertise.

Responsibilities:

  • Own a portfolio of approximately 20–25 member organizations
  • Build trusted, long-term relationships with executives and understand each member’s business context, priorities, and expectations
  • Deliver confidential, objective counsel through virtual and in-person engagements, including onsite visits
  • Lead open-ended, value-focused conversations and help executives make confident decisions
  • Guide members through business strategy, AI adoption and governance, cybersecurity and resilience, data, cloud and platform modernization, operating models, talent, financial management, and transformation
  • Provide industry perspective on regulatory, risk, client, operational, and competitive pressures
  • Translate priorities into practical objectives and action plans
  • Connect members with research, analysts, benchmarks, diagnostics, tools, consulting and advisory services, and third-party resources
  • Use operational data, analytics, and emerging advisory capabilities, including CIO Analytics, to ground recommendations
  • Surface emerging issues, risks, and opportunities proactively
  • Partner with Account Directors, Sales Leaders, analysts, and other experts on account planning and member success
  • Document priorities, engagement activity, outcomes, and risks; report on service measures and member value
  • Invest in continuous learning and share executive experience, industry observations, and emerging practices with the Executive Counselor community
  • Travel domestically and internationally for member onsite engagements and InfoTech events

Requirements:

  • 15+ years of progressively senior experience in technology, digital, data, cybersecurity, transformation, professional services, or related disciplines
  • Meaningful experience operating at or directly advising the C-suite
  • Prior experience as a CIO, CTO, CDO, CISO, SVP, Managing Director, or equivalent enterprise leader strongly preferred
  • Record of leading complex enterprise decisions, organizational change, technology transformation, investment prioritization, risk, and executive stakeholder management
  • Strong business and financial acumen, including budgeting and management reporting
  • Significant leadership or executive advisory experience in financial services, insurance, and/or professional services
  • Depth in business models, technology challenges, regulatory obligations, and market trends
  • Experience in relevant segments such as banking, insurance, pensions, wealth and asset management, capital markets, payments, fintech, credit unions, private equity, not-for-profit, or professional services organizations
  • Ability to advise across cultures
  • Executive presence and ability to establish credibility, listen deeply, synthesize complex information, ask difficult questions, and provide clear, practical advice
  • Excellent verbal, written, facilitation, and presentation skills
  • Discretion, integrity, objectivity, and strong service orientation
  • Ability to coordinate support across diverse stakeholders, manage a portfolio independently, and build sustained relationships through adaptable conversations
  • Comfortable utilizing data, analytics, benchmarks, diagnostics, and AI-enabled capabilities
  • Willingness and ability to travel domestically and internationally for member onsite engagements and InfoTech events

Benefits:

  • Confidential, objective counsel and executive partnership
  • Access to InfoTech research, benchmarks, diagnostics, operational insights, expert resources, tools, consulting and advisory services
  • Opportunities to participate in InfoTech events
  • Continuous learning and participation in the broader Executive Counselor community
  • Accommodations available on request throughout the recruitment and hiring process