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Director, Planning & Analysis - Investments, Data,

Job in Boston, Suffolk County, Massachusetts, 02298, USA
Listing for: Liberty Mutual Insurance
Full Time position
Listed on 2026-10-12
Job specializations:
  • IT/Tech
    AI Business & Operations
Salary/Wage Range or Industry Benchmark: 180000 - 240000 USD Yearly USD 180000.00 240000.00 YEAR
Job Description & How to Apply Below
Position: Director, Planning & Analysis - Investments, Data, & Experience
Description

NOTE:
This role will have a hybrid work arrangement (2x/week in office). The preferred office location is Boston, MA.

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 —…
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