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

What You'll Do
Technology Delivery & Portfolio Leadership

• 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, underutilization, and resource constraints.

Technology Operating Model & Continuous Improvement

• 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.

AI Enablement & Technology Operations

• 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.

Chief of Staff to the CTO

• 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 decisions are documented, communicated, tracked, and executed.
• Support executive communications and provide visibility into priorities, progress, risks, and results.

Strategy, Planning & Operational Excellence

• Partner closely with the CTO to convert strategic priorities into executable technology roadmaps.
• Lead annual planning, quarterly planning, and portfolio governance processes.
• Drive operational excellence across both strategic programs and ongoing technology operations.
• Provide data-driven insights that support informed business and technology decisions.
• Ensure technology investments align with enterprise objectives and measurable business outcomes.

Financial Management & FinOps

• Own technology budget planning, forecasting, tracking, and reporting.
• Drive financial accountability across cloud infrastructure, software licensing, vendor management, and technology investments.
• Partner with Finance to improve transparency, forecasting accuracy, and cost optimization.
• Establish FinOps disciplines that enable informed investment decisions and responsible resource stewardship.

Executive Reporting & Organizational Transparency

• Develop executive dashboards, portfolio reporting, and delivery health metrics.
• Create visibility into progress, risks, resource allocation, budget performance, and outcomes.
• Ensure executive stakeholders receive accurate, timely, and actionable information.
• Foster a culture of proactive communication and operational transparency.

Cross-Functional Leadership

• Partner across technology, operations, product, finance, and business functions to align priorities and execution.
• Build trusted relationships that facilitate collaboration, accountability, and effective decision-making.
• Influence stakeholders at all levels through credibility, transparency, and results-driven leadership.
• Serve as the connective tissue between business priorities and technology execution.

Required Qualifications

• 12+ years of progressive technology leadership experience, including large-scale delivery, PMO, portfolio management, or technology operations leadership.
• Proven experience leading enterprise technology portfolios and complex transformation initiatives.
• Experience serving as a Chief of Staff, Technology COO, PMO Leader, Delivery Executive, or equivalent operational leadership role.
• Demonstrated success building and improving technology operating models, governance frameworks, and delivery organizations.
• Strong financial management experience, including budgeting, forecasting, vendor management, and cost optimization.
• Experience leading and developing teams through direct management responsibility.
• Exceptional executive communication and stakeholder management skills.
• Ability to influence decisions and drive accountability across senior technology and business leaders.

Preferred Qualifications

• Experience within Life Insurance, Annuities, Reinsurance, Financial Services, or other highly regulated industries.
• Familiarity with modern software delivery practices, Agile methodologies, portfolio management frameworks, and enterprise technology governance.
• Experience implementing AI-enabled productivity, reporting, automation, or operational management capabilities.
• Knowledge of cloud financial management (FinOps), vendor management, and technology investment governance.

Leadership Characteristics
The successful candidate will be:

• Highly accountable and execution-oriented.
• Data-driven and decisive.
• Comfortable operating in ambiguity while creating clarity for others.
• A trusted advisor who can challenge constructively and influence effectively.
• Skilled at balancing strategic thinking with operational detail.
• Focused on outcomes rather than activity.
• Transparent, collaborative, and resilient.
• Capable of creating alignment across diverse stakeholders without creating unnecessary bureaucracy.

The Solomon Page Distinction

Our teams, comprised of subject matter experts, develop an interest in your preferences and goals and we act as an advisor for your career advancement. Solomon Page has an extensive network of established clients which allows us to present opportunities that are well-suited to your respective goals and needs – this specialized approach sets us apart in the industries we serve.

About Solomon Page

Founded in 1990, Solomon Page is a specialty niche provider of staffing and executive search solutions across a wide array of functions and industries. The success of Solomon Page reflects an organic growth strategy supported by a highly entrepreneurial culture. Acting as a strategic partner to our clients and candidates, we focus on providing customized solutions and building long-term relationships based on trust, respect, and the consistent delivery of excellent results. For more information and additional opportunities, visit: solomonpage.com and connect with us on Facebook, and LinkedIn.

Opportunity Awaits.

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