Executive Counselor, Trusted Advisor to CIOs, Technology Leaders
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Job Description
Executive Counselor at InfoTech advising CIOs and technology leaders across Canadian financial, insurance, professional-services, and not-for-profit organizations. Applying executive judgment, research, analytics, and advisory expertise to strategic decisions.
Responsibilities:
- Own a portfolio of approximately 20–25 member organizations and build trusted, long-term relationships with executives
- Deliver confidential, objective counsel through virtual and in-person engagements, including onsite visits and membership-agreement commitments
- Lead open-ended, value-focused conversations; identify underlying issues, challenge assumptions, evaluate alternatives, and support confident executive decisions
- Guide members on 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 tailored to each member’s sector and market
- Translate priorities into practical objectives and action plans
- Connect members with research, analysts, benchmarks, diagnostics, tools, consulting and advisory services, and relevant third-party resources
- Use operational data, analytics, emerging advisory capabilities, and CIO Analytics where relevant to ground recommendations
- Surface emerging issues, risks, and opportunities beyond members’ immediate requests
- Partner with Account Directors, Sales Leaders, analysts, and other experts on account planning and member success while maintaining advisory independence and trust
- 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
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, management reporting, and connecting technology decisions to enterprise strategy and measurable results
- 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, with ability to advise across cultures
- Experience in one or more 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
- Executive presence; 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 executive counsel and access to InfoTech research, benchmarks, diagnostics, operational insights, expert resources, tools, consulting and advisory services
- Opportunities to extend leadership impact by advising executives across organizations and markets
- Equal opportunity employer committed to diversity and inclusion
- Accommodations available on request throughout the recruitment and hiring process
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