Preet Saini
Verified Expert in Project Management
Project Manager
Madison, WI, United States
Toptal member since March 12, 2021
Preet is a certified project manager and senior scrum master with 18+ years leading enterprise cloud transformation, platform modernization, and regulated technology delivery. She led a $117 million/year global cloud transformation and a Guidewire PolicyCenter modernization across multicountry teams, turning complex needs into structured execution. She's skilled in Agile and SAFe at scale, delivery leadership, stakeholder alignment, and program governance, clarifying high-stakes initiatives.
Project Highlights
Expertise
- Agile Product Management
- Azure
- Feature Backlog Prioritization
- IT Projects
- Project Management
- Project Planning & Execution
- Software Implementation
- Technical Project Management
Work Experience
Senior Delivery Lead | Project Manager - Guidewire PolicyCenter Transformation
AXA XL
- Was accountable for end-to-end delivery governance of a multi-year Guidewire PolicyCenter transformation spanning two workstreams and four Agile teams across Wholesale and Environmental Commercial Lines (P&C).
- Directed delivery execution across Product, Rating, Assembly, Forms, Integration, and Release teams, coordinating Primary & Excess Casualty, Energy, Auto, GL, Umbrella, and Workers Comp product lines.
- Oversaw SAFe/PI-based planning and phased release execution, migrating products onto a unified Guidewire PolicyCenter platform with zero unplanned production outages during migration windows.
- Served as primary delivery owner and escalation point for the SI partner, managing prioritization decisions, dependency resolution, delivery commitments, and risk mitigation across active workstreams.
- Facilitated cross-ART collaboration and release coordination with RTEs and Product Management, ensuring consistent delivery of business outcomes, backlog refinement, program-level transparency, and adherence to SAFe best practices.
- Established cross-functional delivery governance forums, surfacing risks and blockers early and driving clear ownership across business stakeholders, SI partners, and technology teams.
- Planned and facilitated PI sessions, collaborating with cross-functional teams to define objectives, resolve dependencies, prioritize backlog items, and ensure alignment with business strategy and incremental value delivery.
- Partnered with Solution Architecture to ensure PolicyCenter configuration and integrations met enterprise architecture, security, and SDLC standards.
- Maintained executive confidence through structured delivery reporting, PI-level risk dashboards, and proactive escalation as the single point of accountability for program health.
Delivery Lead | Senior Scrum Master - Cloud Transformation & Security Modernization
AXA XL
- Owned full program delivery governance for a $117 million-per-year global cloud transformation and a $19 million-per-year cybersecurity modernization initiative within AXA XL Platform & Automation.
- Led strategy and delivery of a strategic internal developer platform, building global Azure, AWS, and GCP environments to standardize tooling worldwide, delivering MVP baseline in 11 months.
- Owned and prioritized backlog, translating strategic objectives into features, maintaining clear communication with stakeholders, and aligning cross-functional teams to ensure consistent delivery of business value across cloud initiatives.
- Directed strategic internal developer platform (IDP) initiative, building global Azure, AWS, and GCP environments, delivering MVP baseline in 11 months, coordinating internal teams and third-party vendors to enable developer productivity worldwide.
- Directed cloud migration execution across engineering, DevOps, testing, security, and DBA teams spanning the US, UK, France, and India, managing cross-regional dependencies and escalations.
- Enforced enterprise cloud-native modernization policies, including the elimination of virtual machines across non-legacy environments, reducing infrastructure complexity and security exposure.
- Orchestrated quarterly big room planning events and global hackathons across a multi-country org, aligning program roadmaps with real-time prototyping and PI objectives.
- Transitioned delivered solutions into BAU, collaborating with change management and operations to define release cadences, distribute release notes, and implement incident and escalation processes for stable production operations.
- Managed a portfolio of vendor and SI partner relationships, overseeing contract alignment, delivery accountability, and performance governance throughout execution.
Senior Scrum Master
CUNA Mutual Group
- Identified, prioritized, and reduced technical debt based on business impact priority and filters for decision making. Set up the process to prioritize the investments based on filters and discoveries, and allocate funding based on an MVF approach.
- Transitioned Waterfall teams to Agile methodology to deliver fast value to customers.
- Led reporting and performance management team to equip clients with powerful visualization tools that deliver insights across their business and put them in control of their data.
- Provided support to a business portfolio focusing on a multi-year technical debt reduction program with an annual budget of more than $15 million.
- Owned the release management lifecycle, including scheduling, coordinating, and managing releases across the IT for multiple applications.
- Helped teams learn and adopt the Agile Lifecycle Management (ALM) platform along with Lean and Agile practices and principles. This included face-to-face, on-site, and remote consulting and training activities.
Agile Project Manager
CUNA Mutual Group
- Developed the data management architecture for a fully hosted system on Microsoft Azure.
- Coached the team on Agile methodology and best practices and ensured adherence to the Agile methodology to deliver rapid product development and maximum business value.
- Drove the development of metrics at the team, a team of teams, and portfolio levels to support continuous improvement at those levels.
- Acted as a catalyst and champion for change to increase Agile adoption and improve the development team's productivity.
- Helped the development team and stakeholders understand and enable Scrum to improve the product development.
- Partnered with other scrum masters to improve the effectiveness of Scrum.
Project Manager
CUNA Mutual Group
- Led retirement planning services (RPS) portfolio, target operating platform (TOP), and defined contribution investment only (DCIO) solution for a merger and acquisition.
- Transferred CPI plans to a new platform and enhanced the DCIO product by adding fixed annuities on additional trading platforms that accept DTCC/NSCC standards.
- Led change management for the merger and acquisition and transfer of resources.
IT Project Manager
Freelance
- Delivered a tool that can manage workload and track and control core project management elements of scope, quality, time, and cost.
- Led the pilot to test the usability of a new tool. Analyzed the pilot outcomes and conducted further customization and testing to fix pain points.
- Created as-is and to-be process maps and conducted gap analysis.
- Communicated with the end users through numerous requirements gathering sessions for prioritizing and re-prioritizing system requirements for on-time delivery.
Project History
Cloud Transformation and Migration Program
Led a cloud transformation/migration program, building the cloud platform portal that enables the onboarding of applications on Azure cloud and provisions the application shell/skeleton in an automated way.
I led two teams in charge of creating a cloud platform portal and migrating applications to the cloud. I ensured that the platform was developed and deployed successfully to the cloud and that any issues identified during the deployment were addressed in a timely and efficient manner. My work also included coordinating with cross-functional teams such as product owners, architects, developers, testers, and operations to ensure the program’s smooth execution.
Guidewire Policy Center Transformation
- 90% — PI Predictability - Committed Features Delivered on Schedule
- 99% — PI Milestones Delivered on Time
- <5% — Escaped Defects per PI Release
Actuaries and underwriters were hesitant to adopt the new Guidewire system, heavily relying on Excel workflows, which caused resistance to change, inconsistent product configurations, delayed policy issuance, and increased operational risk across multiple P&C lines.
Collaborated with business stakeholders to prioritize critical features in the product backlog, conducted hands-on workshops, and facilitated tailored training to demonstrate Guidewire functionality. Leveraged PI Planning to align phased releases with business priorities, ensured smooth transition from legacy tools, built stakeholder confidence, and drove adoption across actuaries and underwriters while reinforcing standardized workflows, improving efficiency, and supporting enterprise compliance and governance standards.
Delivered 90% adoption of new workflows, cut Excel dependency by 70%, improved data accuracy, streamlined policy configuration/rating, and boosted stakeholder confidence while aligning with program objectives.
Tech Debt Reduction
Supported the business portfolio with a focus on a multi-year technical debt reduction program with an annual budget of more than $15 million.
Managed over eight different teams working on 35 high-priority features and releases. Set up product goals in the minimum viable feature (MVF) approach and operationalized the tech debt. Reformed the teams to start practicing Agile methodology, resulting in higher performance along with empirical control.
Reporting and Performance Management System
Launched a reporting and performance management system and acted as a scrum master on the project.
Equipped B2B clients with powerful visualization tools that deliver insights across their business and put them in control of their data, providing accurate pictures of their members, assets, and organization in real time.
Campaign Services Project
Launched the campaign services automated member engagement platform for B2B businesses.
Served as an Agile lead on campaign services project to enable partners to effectively support initiatives within their plan with reduced impact on their budget. Drove the development of metrics at the team, team of teams, and portfolio level to support continuous improvement at those levels.
Education
Master's Degree in Business Administration (MBA)
The University of Wisconsin–Whitewater - Whitewater, Wisconsin
Certifications
Professional Scrum Master Level II (PSM II)
Scrum.org
Professional Scrum Product Owner I (PSPO I)
Scrum.org
Project Management Professional (PMP)
Project Management Institute, Inc.
Skills
Tools
Microsoft Power BI, VersionOne, Azure Boards, Jira
Paradigms
Agile Product Management, Scrum, Agile, Kanban, Agile Project Management, DevOps, B2B, Lean, Change Management
Platforms
Azure
Other
IT Projects, Project Management, Backlog Management, Microsoft, Scrum Master, Scrum Coaching, Scrum Product Owner, Business Analysis, IT Operations Management (ITOM), Certified ScrumMaster (CSM), Agile Coaching, Project Management Professional (PMP), User Stories, Enterprise Project Management, Stakeholder Management, Software Implementation, Change Leadership, Project Planning & Execution, Product Owner, Feature Backlog Prioritization, Microsoft Teams, Fintech, PI Planning, Requirements, Scaled Agile Framework (SAFe), Technical Project Management, Enterprise Change Management (ECM), Leadership, Negotiation, Innovation, Process Improvement, Loans & Lending, P&C Insurance, Data Analytics, PSM-2, SAFe 4 Advanced Scrum Master, Release Train Engineer (RTE), Agile Release Train (ART), Vendor Management, Guidewire, Compliance, Training
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