Technical Program Manager- Implementation Lead

Canada - Toronto, Remote

Product Strategy/Full time/Remote

Our Product Strategy organization build and run Guidewire’s secure, scalable, AI‑enabled cloud platform that transforms how P&C insurers operate worldwide.

You’ll join a collaborative, outcomes‑driven team that blends product, engineering, cloud operations, and data to deliver reliable, high‑value solutions. We work in a global, hybrid environment, combining deep insurance and cloud expertise with a culture of curiosity, inclusion, and continuous improvement.

As a Technical Program Manager – Implementation Lead, you will own end‑to‑end delivery of complex, multi‑team initiatives that embed AI, GenAI, and cloud platform capabilities into customer deployments and internal platforms. You will connect product strategy to execution, aligning engineering, operations, security, and client stakeholders to improve reliability, security, and gross margin while accelerating adoption of innovations like the Agentic AI Platform and new pricing and underwriting solutions. This role is ideal for someone who thrives in distributed, high‑velocity environments, is comfortable in technical detail, and is energized by driving measurable outcomes across AI, cloud, and data‑driven programs.

What you’ll do

Lead client facing, end‑to‑end planning and execution of complex, multi‑team technical programs across platform, cloud operations, product engineering, data, and security to support PDO’s goals in reliability, security, and gross margin improvement. Partner with engineering, product management, design, QA, business stakeholders, and infrastructure teams to define scope, problem statements, success metrics, and delivery milestones for initiatives such as GenAI “lifts,” cloud reliability improvements, and new platform capabilities. Develop, maintain, and continuously refine integrated program plans—including timelines, dependency maps, risk registers, and release plans—to ensure programs land on time, within scope, and with clearly defined business outcomes. Manage cross‑functional dependencies, proactively identify and remove blockers, and escalate risks with data‑driven options so teams can move quickly while maintaining quality, compliance, and customer trust. Facilitate agile ceremonies, technical deep dives, architecture and design discussions, and regular program syncs that align teams around priorities, trade‑offs, and delivery commitments across loosely coupled domains. Implement and evolve program governance, reporting cadences, and operational best practices that improve transparency, decision‑making, and execution efficiency across PDO and partner organizations. Define and own program‑level KPIs (e.g., reliability, incident metrics, development velocity, technical debt reduction, cloud and data platform adoption, infrastructure stability), track variances, and drive course‑corrections based on data and continuous feedback. Ensure technical readiness for production releases—including security posture, scalability, performance, disaster recovery dependencies, and operational health—aligned with Guidewire’s security and compliance standards. Collaborate with leadership to drive change management, refine processes, and align programs with Guidewire’s broader vision to embed AI and GenAI across products and operations, including initiatives like the Agentic AI Platform and cloud adoption accelerators. Influence platform and tooling direction by identifying opportunities to streamline developer workflows, improve operational efficiency, and better support AI, cloud, and data platform adoption across PDO and other teams. Manage relationships with clients, including contract and SLA considerations, to ensure external dependencies support program outcomes and service reliability. Act as the “glue” that connects high‑velocity, distributed teams, ensuring alignment with Guidewire’s mission to transform how P&C insurers operate through a secure, scalable, AI‑enabled cloud platform. 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.

Required Skills & Experience

5-7+ years of total professional experience, including 2+ years in technical program management driving complex, multi‑team software initiatives, preferably in cloud, infrastructure, or platform environments. Strong understanding of the software development lifecycle and agile or hybrid delivery models, with the ability to work effectively with engineering, product, operations, and security teams. Solid grasp of modern software architecture, cloud systems (e.g., distributed, multi‑tenant SaaS), and platform engineering concepts such as reliability, observability, and scalability. Proven track record of designing and running metrics‑driven programs: defining KPIs, building dashboards or reporting mechanisms, and using data to guide decisions, communicate impact, and improve program performance. Hands‑on experience with engineering planning and tracking tools (e.g., JIRA, Aha!, Confluence, Google Sheets) to manage backlogs, dependencies, and status reporting at scale. Exceptional stakeholder management and communication skills, including the ability to simplify complex technical topics for executives and non‑technical partners, and to drive alignment among diverse viewpoints. Proficiency with change management principles and techniques—able to guide teams through new processes, tools, and ways of working while minimizing disruption and resistance. 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 Skills & Experience

Experience leading programs related to cloud operations, platform reliability, AI/ML or GenAI features, or large‑scale data platforms. Background in or exposure to P&C insurance or other highly regulated industries, particularly in cloud or SaaS environments. Experience with vendor management, including understanding of SLAs, contract implications, and how external partners fit into critical program paths. Prior experience in organizations undergoing significant cloud, AI, or data platform transformation, especially where operational excellence and innovation must be balanced.

The Canadian CAD base salary range for this full-time position is $98,000 - $123,000. Your base pay will depend on your experience, skills, education, training, and location among other factors. All full-time positions or part-time roles working 30 hours or more a week at Guidewire are eligible for benefits that support their health and well-being including health, dental, and vision insurance, paid time off, and a company sponsored retirement plan. In addition, some roles may be eligible for the annual company bonus plan, commissions, and/or long term incentive awards which are contingent on a variety of factors including, but not limited to, company and employee performance.

Interested in this position?

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 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.