Head of Technology Delivery & Execution

What You’ll Do

Technology Delivery & Portfolio Leadership

Our client is seeking an experienced Head of Technology Delivery & Execution to serve as the operational leader of a growing Technology organization. Reporting directly to the CTO, this Senior Director-level role combines the responsibilities of a Technology Chief of Staff, Technology COO, portfolio leader, and delivery executive. This is not a traditional PMO leadership position. They are looking for a highly credible execution leader who can transform technology strategy into measurable outcomes by driving prioritization, governance, capacity planning, delivery excellence, financial discipline, and organizational accountability.

The successful candidate will establish and lead the operating model for Technology, ensuring that the right work is prioritized, sequenced, resourced, executed, measured, and communicated effectively across strategic initiatives and business-as-usual operations. The ideal leader brings executive presence, operational rigor, sound judgment, strong stakeholder management skills, technical fluency, and the ability to influence outcomes across both technology and business teams.

This role represents a unique opportunity to shape how an entire Technology organization operates. You will partner directly with the CTO to improve execution, establish operating discipline, enhance transparency, optimize technology investments, and ensure technology delivers measurable business value.

If you are energized by building operating excellence, driving accountability, and leading large-scale technology execution at the executive level, we would welcome the opportunity to speak with you.

Compensation for this role varies by experience, with a base salary ranging from $170,000 to $220,000 and total compensation ranging from $265,000 to $300,000. The client is unable to provide sponsorship at this time, so only U.S. citizens or Green Card holders should apply.

• Senior Director | Technology Leadership
• Location:
  
  Chicago, IL preferred (Hybrid, 2-3 days per week in office). Open to remote candidates with periodic travel for exceptional talent.
• Industry: Insurance, Life & Annuities, Financial Services, or other highly regulated environments preferred
• Reports To:
  
  Chief Technology Officer (CTO)
• People Leadership:
  Yes, including direct leadership of Project Management, Delivery Management, and Technology Coordination functions

• Serve as the single point of accountability for delivery across the Technology portfolio, overseeing initiatives from intake through implementation.
• Lead and develop the Project Management, Delivery Management, and Technology Coordinator teams through direct management and performance accountability.
• Drive portfolio prioritization, sequencing, and resource allocation across competing demands and initiatives.
• Establish transparent delivery governance, ensuring risks, blockers, and dependencies are identified and addressed early.
• Lead corrective action planning when delivery milestones are at risk and provide clear recommendations to executive leadership.
• Make informed prioritization and tradeoff decisions based on business value, resource capacity, risk, and strategic objectives.
• Own enterprise-wide technology capacity planning and proactively address over-allocation, under utilization, and resource constraints.

• Build, implement, and continuously enhance the Technology operating model.
• Establish consistent delivery standards, methodologies, quality controls, and execution practices across teams.
• Increase organizational throughput, improve predictability, and eliminate delivery inefficiencies.
• Identify and address recurring root causes that negatively impact delivery performance, including process gaps, unclear ownership, reporting challenges, and prioritization issues.
• Create a culture of execution excellence, accountability, and measurable outcomes.

• Assess and improve technology delivery tooling, workflows, automation opportunities, and reporting capabilities.
• Lead the practical application of AI-enabled operating practices across the Technology organization.
• Standardize AI-supported meeting management, documentation, action tracking, status reporting, and decision documentation.
• Connect portfolio management, project delivery, reporting, and operational data into meaningful executive-level insights.
• Leverage automation and emerging technologies to improve efficiency, visibility, and decision-making.

• Manage the operating rhythm of the CTO organization, including leadership meetings, portfolio reviews, decision forums, risk reviews, and follow-up activities.
• Prepare executive materials that clearly articulate decisions, risks, tradeoffs, recommendations, and business impact.
• Translate technology strategy into actionable plans, ownership structures, timelines, and measurable outcomes.
• Ensure leadership…