Director, Planning & Analysis -… at Liberty Mutual · Boston

Description

The Director of Planning leads strategic portfolio planning, financial and workforce planning, executive reporting, and vendor and contract governance for LM Technology's Investments, Data, and Experience (IDE) organization. Reporting to the Senior Director, Strategy, Planning & Resiliency, the Director runs the recurring planning cycles, governance, and consolidated reporting that keep IDE's investments, talent, and objectives aligned to enterprise strategy and expected benefits.

The role proactively manages risks and opportunities across the portfolio, oversees IDE change enablement (communications, training, adoption, and stakeholder alignment), drives continuous improvement and communities of practice, and translates performance data into actionable executive insight.

AI is central to how this role operates, not an add-on. The Director is expected to be a hands-on champion of AI across planning, governance, and reporting — using AI to accelerate forecasting and scenario analysis, to convert large volumes of portfolio, financial, and vendor data into executive-ready insight, and to automate recurring planning and reporting workflows. The Director models AI-first ways of working for the IDE organization, identifies and scales high-value AI use cases, and ensures AI is applied responsibly and in line with enterprise data, security, and governance standards.

Success requires strong financial and operational acumen, executive-ready communication, disciplined governance, fluency in applying AI to business problems, and the ability to lead across a highly matrixed environment with minimal oversight.

Responsibilities Include:

Strategic Portfolio Management & Planning

• Lead recurring strategic planning cycles for IDE, ensuring alignment and execution against strategic goals and expected benefits.
• Drive proactive risk and opportunity assessment across the portfolio, surfacing and managing issues and emerging risks before they affect outcomes.
• Use AI-driven scenario modeling and portfolio optimization to test trade-offs, stress-test plans, and recommend the highest-value allocation of investment and capacity.
• Apply predictive analytics and AI to detect emerging risks and dependencies early by correlating signals across financial, delivery, and operational data that manual review would miss.

Financial & Workforce Planning

• Lead IDE's annual and long-range financial planning: budget development, forecasting, and ongoing management to plan.
• Use AI-assisted forecasting, variance analysis, and anomaly detection to improve forecast accuracy, flag budget drift earlier, and reduce manual cycle time.
• Talent Strategy & Development: lead workforce capacity planning, development, and succession planning (including onboarding/ramp and promotion planning), using AI to model capacity scenarios, identify skills gaps, and inform succession and hiring decisions.
• Culture & Engagement: foster collaboration and continuous improvement across the organization, including building AI literacy and confidence within the team.
• Change Enablement: Support organizational change through communications, training, adoption, and stakeholder engagement and alignment, using AI to tailor communications, generate training content, and measure adoption and sentiment.

Executive Reporting

• Performance measurement & key metrics: define KPIs, track performance, and report progress; maintain the consolidated IDE performance reporting.
• Use AI to automate KPI data consolidation, generate draft dashboards and summaries, and flag anomalies or off-track metrics for review.
• "Tell the Story": turn data into actionable insight — achievements, benefits to the business, emerging challenges, and strategic recommendations for leadership — using AI to synthesize large data sets into clear narrative and to accelerate drafting of executive-ready summaries, while the Director owns the judgment, framing, and recommendations.

Vendor & Contract Management

• Contractor Onboarding: coordinate onboarding of contractors and vendor resources into IDE.
• Consolidated Reporting: maintain a single view of contracts, renewals, obligations, and spend across IDE, using AI to extract and normalize key terms, obligations, and renewal dates from contract documents and to keep the consolidated view current.
• Vendor Relationship / Governance: manage vendor performance, risk, and governance across the vendor landscape, using AI-based analytics to score vendor risk and performance and to surface issues proactively.
• Procurement Liaison: coordinate sourcing, contracting, and renewal activity and identify opportunities for savings, using AI-driven spend analysis to detect consolidation, duplication, and negotiation opportunities.

Process Improvement & Collaboration

• Continuous improvement: drive ongoing improvement of planning, governance, and reporting processes, using AI to identify bottlenecks and automate repetitive, low-value workflows so the team can focus on analysis and decisions.
• Identify, prototype, and scale AI use cases across the planning, reporting, and governance value chain, and establish standards for responsible, governed AI use.
• Communities of Practice: establish and support communities of practice to share standards, tools, and best practices — including AI use cases, prompt libraries, and reusable AI-enabled templates.
• Feedback and adoption: gather feedback and drive consistent adoption of processes, standards, and AI tools.

GCS Planning Liaison

• Serve as IDE's GCS / Cyber liaison: coordinating cyber planning cycle requirements, response to findings, and remediation through project governance.
• Use AI to help triage findings, track remediation status, and correlate cyber data across the portfolio, in line with enterprise cyber and responsible-AI governance requirements.

AI-Enabled Ways of Working

• Act as the IDE role model for applying AI to real business problems, setting the expectation that planning, reporting, and governance work is AI-augmented by default.
• Continuously scan for, evaluate, and prioritize new AI capabilities that can improve speed, accuracy, and insight across the Director's remit.
• Ensure all AI use aligns with enterprise data privacy, security, and governance standards, keeping human judgment and accountability firmly in the loop for decisions and executive recommendations.

Qualifications

• Bachelor's degree in Business, Finance, Information Systems, or a related discipline; Master's degree preferred.
• 10+ years of experience in strategy, portfolio/financial/workforce planning, technology operations, or program management, with 5+ years in a leadership role.
• 10+ years of experience with portfolio risk & opportunity management and organizational change enablement (e.g., communications, training, adoption).
• Strong financial planning, budgeting, and forecasting experience within a technology organization, including managing to investment plan.
• Experience with vendor and contract governance, contractor onboarding, and procurement processes.
• Demonstrated experience applying AI tools to business problems — such as forecasting, scenario modeling, data synthesis, reporting automation, or workflow efficiency — with a track record of turning AI capabilities into measurable outcomes.
• Excellent written and verbal communication with the ability to translate detailed data into concise, decision-ready insight and narrative for executives.
• Strong proficiency with BI reporting tools (e.g., Power BI, Tableau, Domo), Microsoft Excel, PowerPoint, Teams, and SharePoint. Familiarity with AI-enabled productivity and analytics tools (e.g., Microsoft Copilot, Claude, or similar) is expected.
• Consistently demonstrates independent, critical thinking and sound judgment, proactively identifying issues, evaluating options, and taking appropriate action with minimal managerial direction.
• Effectively navigates ambiguity, prioritizes work, resolves issues, achieves desired outcomes, and makes timely and well-informed decisions aligned with organizational objectives.

Preferred Qualifications

• Experience supporting enterprise data, technology strategy, or enterprise transformation functions
• Experience building communities of practice and driving continuous improvement and adoption programs.
• Experience identifying, piloting, and scaling AI use cases across a team or function, and building AI literacy and adoption in others.
• Familiarity with responsible/governed AI practices, including data privacy, security, and keeping human judgment accountable for decisions.
• Familiarity with operational performance measurement, KPI frameworks, and executive storytelling.
• Experience working in a highly matrixed, global, product-focused organization.
• Strong judgment in handling sensitive financial, workforce, and vendor information.

Travel

25%