Senior Director, Technology Delivery & Strategy

Who We Are

Everlake is a leading life insurance company headquartered in Northbrook, IL, with offices in Chicago, IL, and Lincoln, NE. If you have a passion for the insurance business, value working in a dynamic team environment, and are ready to roll up your sleeves to help us achieve best-in-class results, this may be the role for you. At Everlake, you will find the dynamics of a small entrepreneurial organization and the strength of a larger corporation rolled into one. We think big and evolve quickly, backed by a collaborative mindset and a solid financial foundation.

Position Summary

The Senior Director, Technology Delivery & Strategy serves as a senior member of Everlake's Technology leadership team and acts as a strategic advisor and operational partner to the Chief Technology Officer. This role is responsible for driving delivery, execution, planning, governance, operational effectiveness, and portfolio oversight across the Technology organization. The position provides leadership and accountability for ensuring technology initiatives, operational priorities, and strategic objectives are executed effectively and aligned with business goals. 

The successful candidate will oversee technology portfolio management, delivery governance, resource planning, organizational effectiveness, budgeting, and performance reporting. Working closely with technology leaders and business stakeholders, the Senior Director will establish and continuously evolve the processes, operating rhythms, governance frameworks, and performance standards necessary to support efficient execution and transparent decision-making. The role is accountable for ensuring that technology investments, priorities, and resources remain aligned with Everlake's strategic objectives while supporting the continued maturation of the Technology function. 

This position requires a highly effective leader with strong business acumen, operational discipline, and the ability to drive results in a fast-paced environment. The individual must be capable of balancing long-term strategic planning with day-to-day execution while proactively identifying risks, resolving delivery challenges, and improving organizational effectiveness. The successful candidate will be expected to influence outcomes across multiple technology disciplines and business functions while fostering accountability, collaboration, and execution excellence.

The Senior Director, Technology Delivery & Strategy reports directly to the Chief Technology Officer and leads the Project Management, Delivery Management, and Technology Coordination functions. The role partners extensively with Technology leadership, Finance, Risk, Information Security, and business stakeholders to support execution of Everlake's technology strategy, technology investment decisions, and organizational priorities.

Key Responsibilities

• Lead portfolio delivery governance across the Technology organization, ensuring initiatives are prioritized, sequenced, managed, and delivered in alignment with business and technology objectives.

• Provide leadership for Project Management, Delivery Management, and Technology Coordination teams, establishing clear accountability, performance expectations, and execution standards.

• Partner with the CTO and Technology leadership team to develop and execute strategic plans, annual roadmaps, operating objectives, and organizational priorities.

• Establish and continuously improve the Technology operating model, including planning processes, governance forums, delivery standards, performance management, and organizational effectiveness measures.

• Establish and maintain delivery governance processes, portfolio management practices, reporting standards, and operating cadences that support effective decision-making and transparency.

• Drive resource planning and capacity management activities across the Technology organization to ensure alignment between strategic priorities and available resources.

• Identify delivery risks, operational challenges, and execution gaps, and develop mitigation strategies that support successful outcomes.

• Define, monitor, and enhance technology delivery performance metrics, operational effectiveness measures, and organizational productivity indicators.

• Lead continuous improvement initiatives focused on delivery effectiveness, operational efficiency, process optimization, and organizational scalability.

• Partner with Finance to develop and manage the Technology budget, including planning, forecasting, variance reporting, vendor expenditures, and financial governance.

• Drive technology financial management practices, including cloud cost management, vendor oversight, software licensing optimization, and technology investment accountability.

• Develop executive reporting, portfolio dashboards, management updates, Board materials, and strategic communications that communicate progress, risks, priorities, and business outcomes.

• Present technology portfolio performance, investment recommendations, resource requirements, and execution risks to senior leadership and key stakeholders

• Partner with business leaders to ensure technology investments and initiatives support enterprise strategic objectives and deliver measurable value.

• Advise the CTO on operating model improvements, organizational effectiveness, workforce planning, vendor strategy, and execution performance.

• Lead special projects and strategic initiatives as assigned by the Chief Technology Officer.

Qualifications

• Bachelor's degree in Information Technology, Business Administration, Engineering, Finance, or a related field; advanced degree preferred.

• Typically 12 or more years of progressive experience in technology delivery, portfolio management, technology operations, program management, consulting, or related leadership roles.

• Demonstrated experience leading complex technology portfolios, enterprise transformation programs, or large-scale operational initiatives.

• Proven success leading cross-functional teams and driving execution across multiple functions and stakeholder groups.

• Strong understanding of technology delivery methodologies, portfolio governance practices, operational management, financial management, and strategic planning.

• Experience developing and managing budgets, forecasts, financial reporting, vendor relationships, and technology investment planning.

• Demonstrated ability to build executive-level reporting, operational dashboards, and performance metrics that support informed decision-making.

• Strong analytical, organizational, problem-solving, and decision-making skills.

• Excellent communication, presentation, influence, and stakeholder management capabilities, including experience working with executive leadership teams.

• Proven ability to balance strategic priorities with operational execution while driving accountability across teams.

• Experience working within financial services, insurance, or other regulated industries is preferred.

• Familiarity with cloud technologies, technology operations, software development lifecycles, and enterprise technology organizations is preferred.

Benefits

• Medical, dental and vision benefits

•401-k plan

• Incentive Programs (Annual & Long Term)

• Flexible paid time off plan

• Hybrid work environment

• Paid holidays

• Tuition assistance