Senior Project Manager, Professional Services

Summary

As a Project Manager/Senior Project Manager, you'll guide complex Guidewire platform implementations from start to finish-making sure they're delivered on time, within budget, and exceed quality expectations. You'll take full ownership of fixed-price and outcome-based engagements, driving rigorous scope management, financial discipline, and commercial accountability throughout the delivery lifecycle. You'll represent both the client's needs and our internal delivery standards, keeping things running smoothly and ensuring our services bring real, measurable value.

You will coordinate across teams, build strong client relationships, and work closely with senior leaders to deliver on project success and customer satisfaction. You'll bring structured implementation experience-drawing on ERP-style delivery disciplines and sound financial management-to ensure large-scale Guidewire deployments are governed and executed to the highest standard.

Job Description

Key Responsibilities

Communication and Stakeholder Engagement

• Strong communication skills, with an ability to effectively engage with stakeholders at all levels, including regular status reporting and expectation management

• Comfortable presenting project updates and discussing project performance with stakeholders at all levels-including transparent reporting on scope status, financial health, EVM indicators, and milestone billing progress

• Communicate proactively when scope, schedule, or budget assumptions are at risk, facilitating timely decisions and formal change control resolution

• Ability to manage global teams and work with multiple partners or vendors to deliver value

• Build and maintain trusted relationships with client executives, programme sponsors, and delivery teams throughout the engagement lifecycle

Scope Management

• Establish a baseline project scope at engagement outset, ensuring all deliverables, exclusions, and assumptions are formally documented, agreed, and signed off by relevant client stakeholders

• Own and enforce the project's change control process end-to-end-evaluating all change requests for scope, schedule, cost, and commercial impact before recommending approval or rejection

• Maintain a comprehensive Change Control Log, ensuring all changes are assessed, approved through appropriate governance channels, and reflected in updated project baselines

• Partner with Solution Architects and Technical Leads to assess the implementation impact of proposed changes, ensuring effort and cost implications are accurately captured before commitments are made

• Proactively identify and manage scope creep risks-educating client teams on contractual boundaries and the cost of change-to protect both the project's commercial position and the client relationship

• Ensure that all scope changes on fixed-price engagements are commercially rebaselined where required, with updated SOW addenda or Change Orders issued and signed before additional work commences

Financial Management and Reporting

• Own project financial performance end-to-end-tracking budgets, forecasting costs, and managing margin across fixed-price and outcome-based engagements

• Apply Earned Value Management (EVM) methodology rigorously across the project lifecycle, tracking and reporting Planned Value (PV), Earned Value (EV), and Actual Cost (AC) at the workstream and project level

• Produce and present regular EVM performance reports, including Schedule Variance (SV), Cost Variance (CV), Schedule Performance Index (SPI), and Cost Performance Index (CPI)-using these metrics to drive early intervention when performance deviates from baseline

• Maintain and update Estimate-at-Completion (EAC) and Estimate-to-Complete (ETC) forecasts regularly, incorporating actual performance data and risk-adjusted projections to give senior leadership reliable financial visibility

• Design and manage milestone-based billing schedules aligned to contractual terms-defining clear, measurable acceptance criteria for each billing milestone upfront and ensuring delivery evidence is documented and ready to support timely invoicing

• Proactively manage billing milestone achievement, coordinating with client stakeholders to secure formal sign-off and with Finance teams to ensure invoices are raised accurately and without delay

• Identify and escalate financial risks early-including margin erosion, cost overruns, and billing delays-and develop mitigation plans to protect project and portfolio financial health

• Collaborate with Engagement Managers and Finance teams on revenue recognition, project profitability reporting, and period-end financial close activities

Project Delivery and Customer Experience

• Develop and maintain project plans, schedules, and budgets structured around fixed-price or outcome-based commercial models, adjusting plans proactively to protect margin and contractual commitments

• Lead delivery across the full Guidewire implementation lifecycle-including Fit-Gap Analysis, Solution Design, Configuration, System Integration Testing, UAT, and Go-Live Cutover-applying ERP-style phase-gate governance to manage quality and risk

• Define clear project scope and objectives at engagement outset, preventing scope creep through robust change control and aligned stakeholder expectations

• Serve as the primary contact for day-to-day client communication, proactively managing issues, decisions, and risks to maintain delivery momentum

Operational Excellence and Governance

• Apply consistent project frameworks and improve delivery methods over time, incorporating lessons from Guidewire and broader ERP implementation best practices

• Establish phase-gate review structures and go/no-go criteria for key delivery milestones, ensuring quality and readiness before phase progression

• Set up clear governance structures-including project dashboards, weekly status reporting, financial reporting packs, escalation paths, and steering committee cadences-for full transparency at all levels

• Define and enforce formal change control processes that protect fixed-price commercial positions while maintaining constructive client relationships

• Contribute to the development of delivery standards, financial templates, and scope management frameworks that can be reused across the Professional Services practice

Cross-Functional Collaboration

• Work seamlessly with Delivery Engineering, Product, Sales, Finance, and external teams to align delivery and customer outcomes

• Partner with Solution Architects and Technical Leads to maintain alignment between implementation scope, delivery effort, and commercial baselines

• Coordinate SI partners, third-party vendors, and client IT teams in complex multi-party delivery environments-managing interdependencies and shared accountability

• Support handoffs between phases or teams to ensure continuity, financial accuracy, and scope integrity

KPIs & Success Metrics

• Project On-time & On-budget Delivery - Projects delivered within agreed timelines and budget envelopes

• Fixed-Price Margin Performance - Delivery within approved cost envelopes; EAC within tolerance of baseline at each reporting cycle

• EVM Performance - CPI and SPI maintained within agreed thresholds; variances identified and actioned early

• Billing Milestone Achievement - Milestones completed, accepted, and invoiced on schedule with zero billing delays attributable to incomplete delivery documentation

• Scope Governance - All scope changes processed through formal change control; zero uncontrolled scope additions

• Customer Satisfaction - Positive stakeholder feedback and confidence in delivery and financial transparency

Key Skills & Experience

• Strong expertise in managing schedules, scope, and quality across complex enterprise software projects, including fixed-price and outcome-based commercial structures

• Demonstrated ownership of scope management end-to-end-including scope baselining, change control, and commercial re-baselining on fixed-price engagements

• Proven experience applying Earned Value Management (EVM) methodology-producing EV-based financial reports including CV, SV, CPI, SPI, EAC, and ETC for senior stakeholder consumption

• Experience designing and managing milestone-based billing schedules, including the definition of acceptance criteria, delivery evidence management, and invoicing coordination

• Demonstrated experience leading structured implementation lifecycle delivery (Fit-Gap, Design, Configure, Test, Cutover) on Guidewire or comparable ERP/enterprise platforms

• Clear and confident communicator-comfortable presenting financial performance, scope status, and delivery health to both client and internal stakeholders at all levels

• Proactive risk manager and problem solver under pressure, with the ability to protect commercial positions while maintaining client trust

• Financially savvy-able to manage budgets, apply EVM disciplines, produce accurate forecasts, and support revenue recognition and period-end close activities

• Skilled in setting up governance structures, including phase-gate controls, steering committees, financial dashboards, and change control frameworks

• Familiarity with delivery platforms and tools like Jira, Confluence, MS Project, Asana, and Power BI

• Basic understanding of the insurance industry and regional trends

• Ability to travel up to 50% of the time

Preferred Skills & Experience

• 5 - 10+ years of hands-on project or program delivery experience in software or professional services, with demonstrated experience on Guidewire or large-scale ERP implementations (e.g. SAP, Oracle, Majesco, Duck Creek)

• Proven track record delivering fixed-price or outcome-based contracts to time, budget, and quality-with demonstrable experience protecting margin through scope and financial discipline

• PMP, PRINCE2, or other formal project management certifications; EVM-specific training or certification (e.g. PMI-SP, EVP) is highly regarded

• Strong working knowledge of financial management concepts, including Earned Value, revenue recognition principles, and project profitability reporting

• Experience designing milestone billing frameworks and managing the full billing lifecycle from milestone definition through to invoice and cash collection

• Experience with SaaS or cloud-based delivery models

• Background in highly regulated sectors, insurance, or financial services

• Exposure to pre-sales activities, including SOW development, fixed-price proposal construction, and outcome-based commercial modelling

• Experience with remote or multi-region project coordination

• Previous success in mentoring or developing junior project management staff

• Skilled at identifying client retention and expansion opportunities during delivery

• Familiarity with Agile, hybrid, or waterfall methodologies as applied to large enterprise implementations

• Hands-on use of modern PM tools like Microsoft Project, Clarity, Smartsheet, Asana, or Power BI

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.