Director/Sr. Director, Product & Delivery Lead – Special Projects Delivery & AI

What part will you play? 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.

What You’ll Do:

Product & Value Ownership

• 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.

Program & Accelerated Delivery Leadership

• 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.

Business Analysis & Stakeholder Partnership

• 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.

AI Product Oversight & Responsible Enablement

• 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.

How You’ll Work

• 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.

Required Experience & Capabilities:

• 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.

What Sets This Role Apart

• True end-to-end ownership: one leader accountable for vision, program execution, and delivery.
• Startup mindset inside the enterprise: speed, experimentation, and empowered decision-making—paired with delivery discipline.
• AI-aware product and program leadership: shaping how emerging capabilities are applied responsibly and effectively.
• Opportunity to establish delivery patterns and ways of working that can scale beyond the initial initiative.

Success Looks Like

• A clearly articulated product vision supported by a credible, executable delivery plan.
• On-time delivery of high-value capabilities with strong adoption and measurable outcomes.
• Risks and dependencies actively managed with no surprises.
• Stakeholders aligned, informed, and confident in progress and direction.
• AI capabilities that are purposeful, trusted, and embedded into real workflows.

This role intentionally spans multiple traditional roles to accelerate delivery, reduce handoffs, and maximize accountability—aligned to how modern product, program, and delivery organizations operate today.

#LI-SY

#LI-Hybrid

US Work Authorization

US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future.

Pay information:

The base salary offered for the successful candidate will be based on compensable factors such as job-relevant education, job-relevant experience, training, licensure, demonstrated competencies, geographic location, and other factors. The salary for the position is $189k-$260k with a 55% bonus potential.