Director / Sr Director

Markel • Boston, MA

1d

About The Position

If you’re looking for a place where you can make a meaningful difference, you’ve found it. The work we do at Markel gives people the confidence to move forward and seize opportunities, and you’ll find your fit amongst our global community of optimists and problem-solvers. We’re always pushing each other to go further because we believe that when we realize our potential, we can help others reach theirs. Join us and play your part in something special!
Role Overview We are seeking a high-impact, hybrid Product, Program & Delivery Leader to lead an accelerated, high-visibility initiative with a startup mentality. This role is designed for a builder and operator—someone who thrives in ambiguity, moves quickly from idea to execution, and can own outcomes end-to-end. Reporting direct to the Managing Director, Product Solutions & Services, this leader will act as the single-accountable owner for product vision, program and project execution, delivery outcomes, and business alignment—driving speed to market on new insurance products while also owning overall AI product oversight. The role ensures solutions are desirable, feasible, scalable, and delivered with speed, quality, and disciplined execution. This role intentionally blends responsibilities typically split across Product Management, Program & Project Management, Business Analysis, and Agile Delivery leadership, drawing on internal role models and delivery expectations across Product Solutions & Services. Dir / Sr Dir, Product & Delivery Lead – Special Projects Delivery & AI - US & Bermuda

Requirements

• 10+ years experience with P&C / Specialty Insurance required
• Proven experience operating across product management, program/project management, and delivery leadership responsibilities.
• Demonstrated success leading complex, cross-functional programs in fast-paced, change-heavy environments.
• Strong execution discipline: planning, dependency management, risk mitigation, and delivery tracking.
• Strong product instincts: customer focus, value prioritization, and outcome-driven decision-making.
• Hands-on delivery leadership experience using Agile, hybrid, or iterative delivery models.
• Demonstrated experience delivering viable AI-enabled products and data-driven solutions, with the ability to provide informed product oversight (not necessarily hands-on model development).
• Exceptional communication, facilitation, and executive-level stakeholder management skills.
• US Work Authorization
• US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future.

Responsibilities

• Own the problem statement, product vision, success metrics, and delivery outcomes, translating business goals into a clear, executable roadmap and integrated delivery plan.
• Define and prioritize features, capabilities, and experiments based on value, risk, dependencies, and learning velocity.
• Act as the primary decision-maker for scope, sequencing, and trade-offs to maximize business impact.
• Own program and project execution end-to-end: intake, discovery, planning, execution, release, and value realization.
• Develop and manage integrated delivery plans, milestones, dependencies, and critical paths across multiple workstreams.
• Actively manage risks, issues, assumptions, and dependencies (RAID), escalating and resolving proactively.
• Coordinate cross-functional teams (engineering, data, architecture, business, vendors) and actively remove blockers.
• Operate with a startup mindset—lightweight but disciplined governance, rapid iteration, bias to action, and continuous learning.
• Balance speed, quality, and control while managing stakeholder expectations and delivery commitments.
• Serve as the bridge between business and technology, deeply understanding workflows, pain points, and opportunities.
• Translate business needs into clear epics, user stories, acceptance criteria, and delivery-ready requirements.
• Facilitate working sessions, steering forums, and executive updates to drive alignment, decisions, and shared ownership.
• Provide product-level oversight for AI-enabled capabilities, ensuring alignment to business value, usability, and operational readiness.
• Partner with data, engineering, risk, and governance teams to ensure responsible AI practices, transparency, and risk awareness.
• Identify opportunities where AI can accelerate outcomes, automate work, or improve decision-making—without over-engineering or unnecessary complexity.
• Acts as a single accountable owner for product, program, and delivery outcomes—not a handoff coordinator.
• Operates comfortably in ambiguity while imposing clarity through structure, plans, and priorities.
• Uses agile, lean, and traditional delivery practices pragmatically—focused on outcomes, not ceremony.
• Communicates clearly and frequently with executives, sponsors, and delivery teams.

Benefits

• We offer competitive benefit programs that help meet our diverse and changing environment as well as support our employees’ needs at all stages of life.
• All full-time employees have the option to select from multiple health, dental and vision insurance plan options and optional life, disability, and AD&D insurance.
• We also offer a 401(k) with employer match contributions, an Employee Stock Purchase Plan, PTO, corporate holidays and floating holidays, parental leave.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed