Senior Director, Tech Learning Strategy & Delivery

Milwaukee, Wisconsin
Northwestern Mutual
About the Job:

As Senior Director, Technology Learning & Capability Transformation, you will define and lead the strategy for building a future-ready, digitally fluent, and continuously learning technology workforce. You’ll drive innovation in how technical and digital talent learn, grow, and evolve to meet changing business and technology priorities.

You’ll drive innovation in how our technology and digital teams learn, grow, and adapt-ensuring our workforce is future-ready and aligned with business goals. This role partners closely with senior technology, digital, HR, and business leaders to build a culture of continuous learning, technical excellence, and measurable impact.

You will focus on two key segments:

• Deeply technical digital talent: Empower tech and digital employees (engineers, developers, architects, data scientists, etc.) with advanced, personalized learning that accelerate mastery of emerging technologies and drive innovation.

  Deeply technical digital talent: Empower tech and digital employees (engineers, developers, architects, data scientists, etc.) with advanced, personalized learning that accelerate mastery of emerging technologies and drive innovation.

• Enterprise-Wide Digital Capability: Equip all employees-regardless of role or background-with foundational digital skills and mindsets, building a resilient, future-ready workforce that can adapt and thrive as technology transforms our business.

  Enterprise-Wide Digital Capability: Equip all employees-regardless of role or background-with foundational digital skills and mindsets, building a resilient, future-ready workforce that can adapt and thrive as technology transforms our business.

Learning Strategy & Innovation

• Develop and execute a forward-thinking tech and digital learning strategy that advances both deep technical expertise and broad digital fluency.
• Identify future skill needs and emerging trends (AI, cloud, cybersecurity, data science, software engineering) and translate them into actionable, scalable learning programs.
• Champion the adoption of innovative learning technologies (AI-driven personalization, simulations, gamification, mobile learning).

Capability Architecture & Future Skills

• Build a technology capability framework aligned with enterprise tech strategy and architecture priorities.
• Define pathways for emerging skill domains (AI, data engineering, cloud modernization, cybersecurity, DevOps).
• Partner with workforce strategy teams to connect learning to role design, performance, and internal mobility.
• Develop and maintain a “skills intelligence” dashboard to monitor readiness and guide investment decisions.

Learning Program Design & Delivery

• Design and deliver modular, AI-enabled learning journeys and academies that accelerate deep skill mastery and real-world application
• Embed learning in flow of work through tool integration, communities of practice, and project-based upskilling
• Create and deliver reskilling bootcamps to help employees transition into emerging digital roles and build critical new capabilities.
• Develop onboarding bootcamps for new digital teams, accelerating integration and productivity.
• Build and curate engaging content across modalities (e-learning, instructor-led, virtual, on-the-job).
• Partner with Enterprise Talent Design in the design & deployment of learning platforms and tools, ensuring accessibility and impact.

Stakeholder Partnership

• Collaborate with technology leaders, business unit heads, and HR partners to assess needs, align learning solutions, and drive adoption.
• Build strong relationships with internal SMEs and external vendors to source best-in-class content and certifications.
• Partner with Architecture, Engineering, and Data leadership to define critical technical skills and capabilities required to deliver the enterprise digital strategy.

Measurement & Continuous Improvement

• Establish KPIs and leverage analytics to measure learning effectiveness, engagement, and ROI.
• Leverage analytics, AI-based skills inference, and productivity metrics (e.g., engineering velocity, deployment frequency) to quantify capability uplift and business impact
• Use data and feedback to continuously improve programs and learning experiences.

Team Leadership

• Attract and Hire Top Talent: Develop and execute strategies to attract, recruit, and onboard high-caliber learning professionals with expertise in digital, technical, and instructional design. Build a diverse team that brings fresh perspectives and deep subject matter expertise.
• Talent Development & Retention: Foster a culture of continuous growth by providing clear career paths, mentorship, and professional development opportunities for team members. Identify and nurture high-potential talent within the team to ensure a strong leadership pipeline.
• Inspire and Motivate: Set a compelling vision for the team, inspiring innovation, collaboration, and a relentless focus on learner impact. Champion a culture of experimentation, knowledge sharing, and psychological safety.
• Performance Management: Establish clear goals, expectations, and feedback mechanisms to drive accountability and high performance. Regularly assess team capabilities and address skill gaps through targeted development.
• Inclusion & Belonging: Prioritize building an inclusive team culture that values diverse backgrounds, experiences, and viewpoints, ensuring all voices are heard and respected.

What Experience You’ll Bring:

• 10+ years in technical learning, capability transformation, or enterprise digital enablement leadership roles.
• Proven record establishing large-scale digital academies, learning ecosystems, or capability frameworks.
• Experience integrating AI, data analytics, or adaptive learning technologies into enterprise programs.
• Strong project management and change leadership skills.
• Experience with learning platforms, digital content, and data-driven program optimization.
• Excellent communication, stakeholder management, and influencing skills.
• Bachelor’s degree required; Master’s or advanced degree preferred.

Preferred Skills and Leadership

• Change Management – Advanced
• User-Centered Design Process – Advanced
• Program Management – Advanced
• Adult Learning – Expert
• Tech & Digital Acumen – Expert
• Learning Experience Design – Advanced

Compensation Range:

Pay Range – Start:

$123,480.00
Pay Range – End:

$229,320.00
Geographic Specific Pay Structure:

Structure 110:

$135,800.00 USD – $252,200.00 USD Structure 115:

$142,030.00 USD – $263,770.00 USD
We believe in fairness and transparency. It’s why we share the salary range for most of our roles. However, final salaries are based on a number of factors, including the skills and experience of the candidate; the current market; location of the candidate; and other factors uncovered in the hiring process. The standard pay structure is listed but if you’re living in California, New York City or other eligible location, geographic specific pay structures, compensation and benefits could be applicable, click here to learn more.

Grow your career with a best-in-class company that puts our clients’ interests at the center of all we do. Get started now!

Northwestern Mutual is an equal opportunity employer who welcomes and encourages diversity in the workforce. We are committed to creating and maintaining an environment in which each employee can contribute creative ideas, seek challenges, assume leadership and continue to focus on meeting and exceeding business and personal objectives.

Skills KPIs & Metrics (NM) – Expert, Analytical Thinking (NM) – Advanced, Strategic Vision & Planning (NM) – Expert, Cross Functional Partnering & Planning (NM) – Advanced, Performance Management & Reporting (NM) – Expert, Technical & Digital Acumen (NM) – Advanced, Documentation (NM) – Intermediate, Customer Centricity (NM) – Expert, Training Program Design (NM) – Advanced, Learning Management Systems (LMS) (NM) – Advanced, User-Centered Design Process (NM) – Advanced, Adult Learning (NM) – Advanced, Adaptive Communication (NM) – Advanced, Continuous Improvement (NM) – Expert, Vendor Management (NM) – Expert, Program Management (NM) – Advanced, HR Ethics (NM) – Expert, Stakeholder Relationship (NM) – Expert, Talent Development & Planning (NM) – Expert, Accountability (NM) – Expert, Learning Experience Design (NM) – Expert, Process Improvement (NM) – Advanced, Change Management (NM) – Advanced, Learning Agility & Critical Thinking (NM) – Advanced, Business Influence (NM) – Expert, Consulting (NM) – Expert

FIND YOUR FUTURE We’re excited about the potential people bring to Northwestern Mutual. You can grow your career here while enjoying first-class perks, benefits, and our commitment to a culture of belonging.

• Flexible work schedules
• Concierge service
• Comprehensive benefits
• Employee resource groups

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