Senior Director, Technology Delivery & Strategy

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.

The Senior Director Technology Delivery & Strategy serves as a senior member of Everlakes 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 Everlakes 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 Everlakes technology strategy technology investment decisions and organizational priorities.

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.

Bachelors 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.

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