Sr. Director, IT Delivery Lead

Markel•Richmond, VA

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! The Senior Director is responsible for all aspects of the division’s information technology strategy and associated systems. This includes the direct management of dedicated delivery resources as well as oversight of all aspects of technology support and operations pertaining to the division business functions. This role drives overall technology strategy and directs the planning and implementation of technology related business solutions in support of business application in order to improve cost effectiveness, service quality, and business development. Job Description Summary: We are seeking a dynamic and experienced leader to head our Core Digital, WC & Small Commercial Insurance Solutions delivery department. This Senior Director ensures the technology landscape of a Fortune 500 insurance company remains robust, secure, efficient, and compliant within a highly regulated industry. This role will oversee the delivery and operations of Digital, Underwriting, Rating and other critical insurance solutions that support our growing Programs and Solutions business division, specifically Workers Compensation and Small Commercial. This leader is critical to enabling the scale, speed, and reliability required to support the continued growth of Markel’s Programs and Solutions business, ensuring underwriting and digital platforms evolve in step with business strategy. The ideal candidate delivers measurable improvements in platform stability, delivery excellence and total cost of ownership while leading large-scale underwriting and digital transformations.

Requirements

15+ years of progressive experience leading enterprise scale technology delivery and operations, including accountability for security, controls, and regulatory compliance; preferably in the insurance industry.
Proven leadership experience managing multi-disciplinary teams with a mix of vendor partners and internal resources with a focus on culture, talent development, and succession planning.
Strong knowledge and proven track record utilizing a wide range of technologies (SaaS, Private Cloud, On-Prem) to drive business results in a cost-effective way.
Deep understanding of technology delivery processes, tools and techniques across the entire lifecycle.
Ability to evaluate and challenge vendor or engineering estimates based on execution experience, with a track record of making sound trade-off decisions balancing quality, cost, and timeline.
Strong knowledge of Governance, Risk, and Compliance frameworks (e.g., COBIT, SOX).
Solid understanding of complete insurance lifecycle for both admitted and non-admitted product offerings
Excellent strategic thinking, planning, and communication skills.
Deep knowledge of the line of business with the ability to develop and leverage business and/or vendor partnerships, consult on business priorities, and optimize value through solution identification aligned with business objectives.
Proven ability to develop and implement technology roadmaps and operational strategies.
Strong collaboration skills with the ability to work across multiple teams and geographies.
Proven track record establishing, managing, and communicating large technology budgets that incorporate software, infrastructure, and labor costs.
US Work Authorization US Work Authorization required. Markel does not provide visa sponsorship for this position, now or in the future.

Nice To Haves

Experience working in regulated industries (Insurance and/or Financial Services).
Familiarity with enterprise architecture frameworks and agile delivery methodologies.
Experience with large-scale, distributed systems and multi-cloud environments.
Strong project management and vendor management skills.

Responsibilities

Accountable for end‑to‑end delivery, operational performance, and lifecycle management of core Digital, Underwriting, and Rating platforms
Collaborate closely with Markel executives, business leadership, enterprise architecture, and other key stakeholders to align technology strategy and execution plans.
Partner with architecture and data teams to enable adoption of AI‑enabled capabilities within underwriting and digital platforms, aligned with governance and risk standards.
Define and execute a multi‑year technology roadmap for Core Digital platforms across U.S. and Bermuda divisions, aligning business priorities, architecture standards, and investment decisions.
Own underwriting transformation outcomes, including delivery predictability, quality, and business value, using clearly defined KPIs that are reviewed and reported regularly.
In collaboration with other technology delivery teams, drive modern engineering practices, including cloud‑native design, and DevSecOps to improve speed, quality, and resilience of core platforms.
Ensure ongoing compliance with governance, risk, and control requirements by embedding GRC practices into delivery and operations, with clear ownership and audit-ready evidence.
Build and sustain a high-performing team through active coaching, succession planning, and talent development across internal staff and vendor partners.
Foster a culture of continuous improvement, innovation, and operational excellence within the team(s).

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.

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