Technology Program Lead

About the role

Seasoned Program Lead with deep expertise in enterprise platforms, AI, and large-scale technology transformations, driving execution, stakeholder alignment, and business outcomes in complex environments. Reporting to the Head of IT Operations, this role partners closely with line of business CIOs, technology leaders, and cross-functional teams to drive execution of strategic technology priorities across multiple businesses.

Responsibilities

• Strategic Program Leadership & Execution
  • Drive execution across a matrixed portfolio spanning multiple Strategic Businesses and technology organizations by creating alignment among teams with different priorities, leadership structures, funding models, and delivery accountabilities.
  • Translate strategic priorities and technology roadmaps into clear execution plans, milestones, owners, dependencies, decision points, and measurable outcomes.
  • Influence outcomes without formal positional authority by establishing clear commitments, building stakeholder alignment, creating transparency around execution, and constructively challenging teams when commitments or outcomes are at risk.
  • Establish the operating cadence required to drive programs forward, including leadership reviews, working sessions, milestone reviews, and escalation forums.
  • Maintain integrated program plans and provide clear visibility into progress against commitments.
  • Proactively identify execution risks, dependencies, resource constraints, and decision gaps that could impact delivery.
  • Drive issues to resolution by bringing together the appropriate business, technology, architecture, data, security, finance, and vendor stakeholders.
  • Coordinate execution across related workstreams and teams to ensure sequencing, dependencies, and handoffs are actively managed.
  • Support strategic initiatives across areas such as AI, data, platform modernization / rationalization, and technology operating model transformation.
  • Create clarity in ambiguous situations by structuring problems, defining actions, establishing ownership, and driving decisions.
• Execution Management & Value Realization
  • Define clear program objectives, success measures, KPIs, and expected business and technology outcomes.
  • Establish mechanisms to measure whether strategic initiatives are delivering their intended value, not simply completing milestones.
  • Track execution against agreed milestones, commitments, outcomes, financial expectations, and key performance indicators.
  • Use data and program insights to identify areas requiring leadership attention, intervention, or changes in approach.
  • Partner with Finance and initiative leaders to maintain visibility into program financials, investment assumptions, and expected benefits.
  • Identify execution trends and recurring barriers across initiatives and recommend changes to improve delivery effectiveness.
  • Ensure decisions, actions, risks, dependencies, and commitments are clearly documented and actively managed through resolution.
  • Establish and drive shared accountability across workstreams where delivery resources, funding, priorities, and decision rights may span multiple organizations, ensuring commitments remain visible and are actively managed through completion.
• Cross-Business Coordination & Dependency Management
  • Connect initiatives and teams across Strategic Businesses to identify shared dependencies, opportunities, and execution risks.
  • Maintain visibility into critical cross-program and cross-business dependencies and ensure owners and resolution plans are established.
  • Identify opportunities to leverage shared technology capabilities, platforms, vendor solutions, and delivery approaches across businesses.
  • Partner with architecture, engineering, data, cybersecurity, infrastructure, and other enterprise technology teams to remove barriers to execution.
  • Coordinate with Product Owners, Program Managers, Engineering Leaders, and other delivery roles without duplicating their day-to-day responsibilities.
  • Escalate issues requiring executive intervention with a clear articulation of the problem, impact, options, and recommended action.
• Executive Engagement & Continuous Improvement
  • Serve as a trusted execution partner to Strategic Business CIOs and senior technology leaders.
  • Provide leadership with a concise and objective view of what is on track, what is at risk, what decisions are required, and where intervention is needed.
  • Translate complex program information, technology considerations, and execution challenges into clear executive-level communications.
  • Ensure leadership decisions are translated into actions, owners, and measurable commitments and followed through to completion.
  • Leverage approved AI tools to improve program planning, analysis, executive communications, meeting effectiveness, risk identification, and decision support.
  • Identify opportunities to automate repetitive program-management activities and shift capacity toward higher-value analysis and execution.
  • Continuously improve program execution methods, governance mechanisms, tools, and reporting based on lessons learned and emerging capabilities.

Qualifications

• Bachelor's degree in Computer Science, Engineering, Information Systems, Business Administration, or a related field; advanced degree or relevant certifications such as PMP, Agile, or Scrum are a plus.
• 8 years of experience leading and executing complex technology programs, preferably within Insurance or Financial Services.
• Demonstrated ability to drive large, cross-functional initiatives from strategy through execution and measurable outcomes.
• Strong understanding of software development, technology platforms, infrastructure, data, Cybersecurity, and emerging AI technologies.
• Proven ability to identify and manage complex dependencies, risks, milestones, and competing priorities across a matrixed organization.
• Ability to operate effectively without direct authority over the teams responsible for delivery.
• Excellent PowerPoint and data visualization skills, with demonstrated ability to turn complex information into concise executive-level insights.
• Strong proficiency using AI capabilities and tools such as ChatGPT, Microsoft Co-pilot, Gemini, Claude, or similar technologies to improve productivity and decision support.
• Strong interest and curiosity in technology innovation, AI, and designing more efficient ways of working.
• Experience with Jira, Microsoft 365, and related program and collaboration tools.
• Product Owner, Business Analyst, engineering, or technology delivery experience is a plus.
• Exceptional communication, structured problem-solving, organization, and stakeholder-management skills.