Senior Director, Talent Management and Development

Guidewire Software

4d•$205,000 - $307,000

About The Position

The Global People & Operations Team at Guidewire scales, shapes, and strengthens the company by building the capabilities, culture, and clarity needed for our future. We focus on technology-enabled, globally scalable people practices that elevate employee experience, accelerate growth, and embed AI and automation into how we work. As a team, we prize accountability, transparency, and impact, guided by values of courage, curiosity, and commitment. This Senior Director role leads the architecture of Guidewire’s enterprise talent system so our workforce can execute today and as we scale and increase complexity. You will design and integrate the core systems that define performance, grow leaders, plan future workforce needs, and build readiness for critical roles. You’ll be a key strategic partner in an AI-first, cloud-based insurance technology company, ensuring talent is a differentiator in how we transform the P&C insurance industry for our customers worldwide. The role will lead a team of talent development specialists and experts globally.

Requirements

Demonstrated ability to embrace AI and apply it to your current role as well as data-driven insights to drive innovation, productivity, and continuous improvement.
Extensive experience (typically 12+ years) in talent management, leadership development, and/or organizational development, with significant time spent leading enterprise talent strategies in complex, global organizations.
Proven track record designing and operationalizing integrated talent systems (performance, succession, leadership development, assessment) that measurably improve capability, leader effectiveness, and business outcomes.
Deep expertise in modern performance management, including calibration, differentiation, and enabling leaders to hold clear, fair, and growth-oriented performance and accountability conversations at scale.
Experience building succession and readiness strategies for critical roles, including use of robust assessment tools, potential frameworks, and data to identify risk and inform decisions.
Demonstrated ability to design and scale leadership development and capability-building programs that drive observable behavior change, with emphasis on business acumen, industry fluency, and comfort with AI-powered tools.
Strong, pragmatic stakeholder management skills with senior executives; able to translate strategy into clear talent implications, influence decisions, and drive cross-functional execution across Global People, business leaders, and Talent Attraction.
Comfort working in a high-change, growth-oriented, technology-driven environment, balancing structure with agility and continuously improving practices based on feedback and data.

Nice To Haves

Experience in a global technology, SaaS, or enterprise software company, ideally with exposure to the insurance or financial services sectors.
Prior leadership of talent or leadership development functions that support AI and automation adoption or large-scale digital and operating model transformations.
Advanced degree in Organizational Psychology, HR, Business, or a related field, or equivalent experience.
Familiarity with skills frameworks, job architecture, and career pathways, and how they connect to performance, development, workforce planning, and employee experience.

Responsibilities

Architect and own Guidewire’s enterprise talent strategy, integrating performance management, leadership development, succession, assessment, and workforce planning into a coherent, data-informed system that scales globally.
Define and continuously refine clear, role-specific performance expectations and success profiles that align to Guidewire’s strategy, AI-first operating model, and Global People FY26 priorities around capability, readiness, and scale.
Establish and embed disciplined performance management practices, including calibration, performance differentiation, and defined talent strategy, in close partnership with Senior People Business Partners and People leaders globally.
Lead enterprise talent management, including building visibility into leadership bench strength, defining readiness and potential against future business needs, and surfacing talent and leadership risks early through robust assessment and succession approaches.
Design and scale leadership and critical capabilities development (for example, business acumen, P&C industry depth, AI fluency) that are tightly connected to performance, succession, hiring standards, and the Global People skills framework.
Partner with Talent Acquisition, People Operations, and regional People leaders to build scalable talent engines in growth markets, improve quality of hire, and reduce downstream performance and readiness risk.
Use workforce, engagement, and readiness data as leading indicators to support VPMOM methods, guide talent investments, and ensure the talent system remains a business enabler as Guidewire advances its AI-powered cloud platform for P&C insurers.
Strong leadership and organizational skills to manage a global team of people. This role requires clear communication across time zones, setting priorities, and ensuring work stays aligned with team and company goals. The leader will provide guidance, regular feedback, and support to help team members succeed while maintaining accountability and collaboration. Success in this role requires good communication, problem-solving, cultural awareness, and the ability to keep a remote team engaged and productive.