Technology Upskilling & Enablement Leader

Overview

Responsible for designing and executing a future-focused learning strategy that enables the upskilling and reskilling of the technology workforce. This role partners across technical domains to align learning initiatives with evolving technical capabilities, drive leadership development, and embed a culture of continuous learning that supports innovation, agility, and digital transformation.

You will: (Key Responsibilities)

Learning Strategy & Alignment

• Develop and implement training initiatives that improve talent management and emerging technical proficiencies (e.g., Engineering, Cloud, DevOps, Data, AI, Agentic AI).
• Research and assess external learning environment to launch learning platforms, tools, and vendor partnerships as part of a multi-modal training experience.
• Perform assessments of skills gaps in various technical areas and propose focused training programs to address proficiency gaps.
• Present executive level strategic roadmaps, as well as conduct/facilitate learning sessions across diverse audiences.
• Establish KPIs and report on training effectiveness and business impact.

Leadership Training & Manager Enablement

• Design and deliver leadership development programs tailored to support the business and technology operating model.
• Establish best practices for managers to champion technical upskilling and talent development within agile and product-centric teams.
• Partner with HR, engineering, and product leaders to embed learning into performance management, career progression, and technical competency frameworks; ensure leadership programs and other applicable areas align to enterprise approach.

Culture of Continuous Learning

• Lead initiatives that promote a growth mindset, technical curiosity, and innovation across engineering and IT teams.
• Drive engagement through learning campaigns, recognition programs, and storytelling that highlight learning success and impact.
• Monitor and report on learning adoption, engagement, and business impact using data-driven insights and feedback loops.

Governance & Stakeholder Engagement

• Define governance models for learning program delivery, vendor management, and effectiveness measurement.
• Collaborate with technology leaders, HR, and external partners to ensure learning initiatives are relevant, scalable, and future-ready.
• Learning programs are aligned to workforce planning and future technology skill needs.

You have: (Qualifications)

• Bachelor’s degree in Organizational Development, Education, Human Resources, or a related field; technical background or experience in IT/engineering preferred.
• 7+ years of experience in learning and development, with a focus on technology or digital organizations.
• Proven experience designing and implementing learning strategies for technical audiences.
• Experience with product management, cloud, data, DevOps, AI, or software engineering learning programs is highly desirable.
• Strategic execution: ability to successfully build targeted learning programs across platforms (e.g., Pluralsight, Coursera, Udemy, Degreed) and technical certification programs (e.g., AWS, Azure, Google Cloud, Kubernetes).
• Data analysis: practiced in analyzing learning data and translate insights into actionable improvements.
• Proficiency in current learning methods like hands-on labs, simulations, and AI driven
• Strategic thinking: ability to translate technology trends into learning priorities.
• Strong stakeholder management and influencing skills across technical and non-technical audiences.
• Excellent communication and facilitation skills, especially with engineering and IT leaders.
• Change leadership and ability to foster a learning culture within fast-paced, agile environments.
• Collaborative approach with a passion for developing technical talent and innovation.

Salary Range:

$116,350.00 - $191,155.00

The salary range reflected above is a good faith estimate of base pay for the primary location of the position. The salary for this position ultimately will be determined based on the education, experience, knowledge, and abilities of the successful candidate. In addition to salary, this role may also be eligible for annual, sales, or other incentive compensation.

Our Promise

At Guardian, you’ll have the support and flexibility to achieve your professional and personal goals. Through skill-building, leadership development and philanthropic opportunities, we provide opportunities to build communities and grow your career, surrounded by diverse colleagues with high ethical standards.

Inspire Well-Being

As part of Guardian’s Purpose – to inspire well-being – we are committed to offering contemporary, supportive, flexible, and inclusive benefits and resources to our colleagues. Explore our company benefits at www.guardianlife.com/careers/corporate/benefits. Benefits apply to full-time eligible employees. Interns are not eligible for most Company benefits._

Equal Employment Opportunity

Guardian is an equal opportunity employer. All qualified applicants will be considered for employment without regard to age, race, color, creed, religion, sex, affectional or sexual orientation, national origin, ancestry, marital status, disability, military or veteran status, or any other classification protected by applicable law.

Accommodations

Guardian is committed to providing access, equal opportunity and reasonable accommodation for individuals with disabilities in employment, its services, programs, and activities. Guardian also provides reasonable accommodations to qualified job applicants (and employees) to accommodate the individual's known limitations related to pregnancy, childbirth, or related medical conditions, unless doing so would create an undue hardship. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact applicant_accommodation@glic.com.

Current Guardian Colleagues: Please apply through the internal Jobs Hub in Workday.