Executive Counselor (Trusted Advisor to CIOs & Technology Leaders) | Financial Services, Insurance, Professional Services & Not-for-Profit

The Opportunity

Turn the judgment and instinct you've built as an executive into counsel for leaders shaping the future of their business and technology. As an Executive Counselor at InfoTech, you will advise, challenge, and support CIOs and senior technology, digital, data, and business leaders across Financial Services, Insurance, Professional Services & Not-for-Profit.

You will combine executive judgment with InfoTech research, benchmarks, diagnostics, operational insights, and expert resources to help members clarify priorities, evaluate trade-offs, manage risk, and translate technology investments into valuable business outcomes. Through confidential, candid conversations, you will strengthen their decision-making, leadership effectiveness, and influence.

What you will do

• Own a portfolio of approximately 20–25 member organizations, building trusted, long-term relationships with their executives and learning each member’s business context, priorities, and expectations.

• Deliver confidential, objective counsel through virtual and in-person engagements, including onsite visits and other commitments under the membership agreement.

• Lead open-ended, value-focused conversations; identify the underlying issue, challenge assumptions respectfully, evaluate alternatives, 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.

• Bring an informed industry perspective to regulatory, risk, client, operational, and competitive pressures, tailoring advice to the member’s sector and market.

• Translate priorities into practical objectives and action plans, connecting members with appropriate research, analysts, benchmarks, diagnostics, tools, consulting and advisory services, and relevant third-party resources.

• Use operational data, analytics, and emerging advisory capabilities, including CIO Analytics where relevant, to ground recommendations in the member’s environment.

• Proactively surface emerging issues, risks, and opportunities, bringing forward useful perspectives and ideas beyond the member’s immediate request.

• Partner with Account Directors, Sales Leaders, analysts, and other experts on account planning and member success while maintaining the independence and trust of the advisory relationship.

• Document priorities, engagement activity, outcomes, and risks; report on service measures and member value to support continuity and continuous improvement.

• Invest in continuous learning and share executive experience, industry observations, and emerging practices with the broader Executive Counselor community.
  
  

Travel and member engagement

Willingness and ability to travel domestically and internationally for member onsite engagements and InfoTech events. Travel varies with the assigned portfolio, member commitments, location, and event participation.

What you bring

Executive leadership and business judgment

• 15+ years of progressively senior experience in technology, digital, data, cybersecurity, transformation, professional services, or related disciplines, with 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 is strongly preferred.

• A record of successfully 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.

Industry expertise

• Significant leadership or executive advisory experience in financial services, insurance, and/or professional services, with depth in business models, technology challenges, regulatory obligations, and market trends, as well as the 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 (PE), not for profit, or professional services organizations.

Advisory and relationship skills

• Executive presence and the ability to establish credibility, listen deeply, synthesize complex information, ask difficult questions, and provide clear, practical advice.

• Excellent verbal, written, facilitation, and presentation skills, with the ability to simplify complexity and adapt to different personalities and leadership styles.

• Discretion, integrity, objectivity, and a strong service orientation; confidence to offer constructive challenge and openness to being challenged.

• The ability to coordinate support across diverse stakeholders, manage a portfolio independently, and build sustained relationships through adaptable conversations rather than scripted approaches.

Modern advisory capability

• Comfortable utilizing data, analytics, benchmarks, diagnostics, and AI-enabled capabilities alongside executive experience to inform decisions.
  
  

Why join InfoTech

Extend the impact of your leadership experience by advising executives across organizations and markets. You will combine personal executive partnership with research, operational evidence, and expert support to help leaders navigate complexity and make better decisions.

InfoTech is an equal opportunity employer committed to diversity and inclusion. We welcome qualified applicants without regard to legally protected characteristics. Accommodations are available on request throughout the recruitment and hiring process.

Infotech is an equal opportunity employer committed to diversity and inclusion and does not discriminate on the basis of any legally protected status or characteristic including Minority/Female/Sexual Orientation/Gender Identity/Disability/Veteran and are pleased to consider all qualified applicants. To that end, upon request, Infotech will ensure, to the extent possible, that accommodation be made available to applicants throughout the recruitment and hiring process.

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