Summary

The People – Talent Attraction team builds the capabilities, culture, and clarity Guidewire needs for continued growth. We partner globally to strengthen talent engines, improve candidate and employee experiences, expand inclusive leadership pipelines, and use technology, data, and automation to work smarter. Our environment is collaborative, curious, accountable, and focused on continuous improvement, with a strong emphasis on AI fluency and scalable hiring practices.

This role leads confidential, high-impact searches for senior leaders who will help Guidewire transform how the world’s property and casualty insurers do business. You will shape executive hiring strategy, advise senior stakeholders, and build trusted relationships with exceptional passive talent across technology and SaaS markets. Your work will strengthen leadership capability, support Guidewire’s growth, and contribute to a consistent, high-quality candidate experience.

Job Description

What you’ll do

• Lead end-to-end executive searches for VP, Director, Head of Engineering, Product, Sales, and other senior leadership roles, translating business priorities into clear search strategies and measurable outcomes.
• Partner with executives, hiring managers, Human Resources Business Partners, and business leaders to define leadership requirements, assess organizational needs, and align hiring decisions with Guidewire’s growth plans.
• Build talent maps, competitor intelligence, and sustained pipelines across SaaS, cloud, cybersecurity, artificial intelligence, machine learning, and technology-product organizations.
• Identify and engage passive candidates through executive search partners, professional networks, referrals, LinkedIn Recruiter, and industry relationships while maintaining discretion and confidentiality.
• Assess leadership capability, strategic thinking, team-building, product-led growth experience, SaaS understanding, and alignment with Guidewire’s collaborative and purpose-driven culture.
• Manage complex interview processes, influence selection decisions, and coordinate compensation benchmarking, equity or long-term incentive considerations, and offer negotiations with the appropriate teams.
• Deliver a personalized, high-touch executive candidate experience and provide leaders with market insights on talent availability, competitor movement, diversity, compensation, and hiring trends.
• Track and communicate executive hiring metrics, including time to fill, pipeline conversion, offer acceptance, source effectiveness, and hiring outcomes, using data to improve recruitment strategy and execution.
• At Guidewire, we foster a culture of curiosity, innovation, and responsible use of AI—empowering our teams to continuously leverage emerging technologies and data-driven insights to enhance productivity and outcomes.

What you’ll bring

Required

• Significant experience leading executive search and senior leadership hiring in a technology, SaaS, cloud, cybersecurity, or comparable product-company environment.
• Minimum 15 years of experience into Recruitment (Min. 10 years into Executive Hiring)
• Demonstrated ability to engage passive candidates and build trusted relationships with senior leaders and executive-level talent.
• Strong stakeholder-management and advisory skills, with the judgment and confidence to influence hiring decisions at senior levels.
• Experience developing talent maps, market intelligence, competitor insights, and proactive leadership pipelines.
• Skilled leadership assessment capabilities, including evaluation of strategic thinking, organizational leadership, team development, business impact, and cultural contribution.
• Experience partnering on executive compensation benchmarking and negotiating complex offers involving incentives, equity, or long-term rewards.
• Excellent communication, organization, discretion, and prioritization skills, with the ability to manage multiple confidential searches and deliver timely outcomes.
• 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.

Preferred

• Degree preferred or equivalent professional experience.
• Experience recruiting leaders for global organizations or across multiple international markets.
• Familiarity with property and casualty insurance, InsurTech, cloud platforms, artificial intelligence, machine learning, cybersecurity, or enterprise software.
• Experience using applicant tracking systems, talent-intelligence tools, executive-search analytics, and structured assessment approaches.
• Experience advancing inclusive leadership hiring through broad sourcing strategies and consistent, job-related evaluation practices.

Your Impact

We believe in clarity and setting you up for success. In your first six months, you will establish trusted partnerships with senior stakeholders, understand Guidewire’s leadership priorities, create targeted talent maps for critical functions, and build or strengthen executive pipelines across priority technology markets. You will introduce clear search strategies, provide actionable market intelligence, improve pipeline and source reporting, and help deliver an efficient, confidential candidate experience. Your work will support scalable growth, stronger leadership capability, and the continued evolution of Guidewire as a cloud and AI platform committed to customer success.

What’s in it for you

The people we employ give their all, and in return, we offer flexibility wherever we can, such as:

• Flexible work environment
• Health and Wellness benefits
• Paid time off programs including volunteer time off
• Market-competitive pay and incentive programs
• Continual development and internal career growth opportunities

Guidewire combines digital, core, analytics, and AI to deliver its platform as a cloud service and is committed to customer success. You will join a culture grounded in determination, collaboration, continuous improvement, and bravery, where people are encouraged to learn, contribute, and grow together.

Guidewire embraces a culture of in-person interviews for all applicants and onsite orientation for all new hires.

Guidewire is committed to providing an inclusive, respectful, and accessible hiring experience. Employment decisions are based on role-related qualifications, business needs, and organizational requirements. We welcome varied perspectives and do not make assumptions about candidates based on personal characteristics or background.

About Guidewire

Guidewire is the platform P&C insurers trust to engage, innovate, and grow efficiently. We combine digital, core, analytics, and AI to deliver our platform as a cloud service. More than 540+ insurers in 40 countries, from new ventures to the largest and most complex in the world, run on Guidewire.

As a partner to our customers, we continually evolve to enable their success. We are proud of our unparalleled implementation track record with 1600+ successful projects, supported by the largest R&D team and partner ecosystem in the industry. Our Marketplace provides hundreds of applications that accelerate integration, localization, and innovation.

For more information, please visit www.guidewire.com and follow us on Twitter: @Guidewire_PandC.

Guidewire Software, Inc. is proud to be an equal opportunity and affirmative action employer. We are committed to an inclusive workplace, and believe that a diversity of perspectives, abilities, and cultures is a key to our success. Qualified applicants will receive consideration without regard to race, color, ancestry, religion, sex, national origin, citizenship, marital status, age, sexual orientation, gender identity, gender expression, veteran status, or disability. All offers are contingent upon passing a criminal history and other background checks where it's applicable to the position.

Guidewire is proud to be a disability inclusive employer. We are committed to providing individualized accommodations and support to candidates for any part of our hiring process. If you think you may need disability-related accommodations, please email EmployAbility at [email protected], our disability partner, or schedule a call with an EmployAbility expert (calendar booking slot) for a confidential conversation.