Technology Strategy Analyst

Location: Glen Allen, VA

Job Type: Full-Time

Target Salary Range*: $70,000 - $105,000

*This represents the potential salary range for this position depending on education level, years of experience and/or certifications in addition to other position specific requirements which may impact salary

The Technology Solutions Strategy & Planning team is seeking an analytical and motivated Technology Strategy Analyst with strong communication skills.

The Technology Solutions Strategy & Planning team is responsible for developing Markel’s 3–5 year technology and capability roadmap across its U.S. and Bermuda insurance businesses. The team operates at the intersection of business strategy, technology, and transformation, ensuring that investments are aligned to growth, profitability, and operational efficiency goals.

The Technology Strategy Analyst will support enterprise-wide strategic initiatives by combining structured problem solving, coordination and execution rigor, and analytical research. This is a high-visibility role that interacts directly with senior business and technology leaders and contributes to decisions on investment priorities, transformation sequencing, and capability development.

• Support business strategy discovery by planning and coordinating sessions with business, technology, and other key stakeholders.
• Support strategy development and decision-making by translating strategic priorities of business leaders into technology and capability needs.
• Post-strategy discovery sessions, summarize key outcomes, decisions, and next steps for stakeholder communications.

• Gather and analyze data on internal systems, capabilities, and processes across product lines to identify gaps and opportunities within the technology landscape supporting each business unit.
• Conduct market research and translate findings into actionable insights.
• Translate findings into concise, business-friendly recommendations.
• Develop clear, executive-ready PowerPoint presentations.

• Translate subsequent technology solutions due diligence activities into structured project plans, timelines, and deliverables.
• Track progress across workstreams and proactively follow up to ensure timely completion.
• Assist in building and maintaining multi-year technology and capability roadmaps.
• Consolidate roadmap views across business units and surface cross-functional dependencies.

• Collaborate with business, technology, and finance stakeholders to develop business cases and CBAs.
• Support financial analyses of technology investments.

• 2–5+ years of experience in one or more of the following:
  • Management consulting or strategy
  • Insurance, including carrier, broker, or advisory
  • Technology strategy, operations, or transformation
• Experience working across business and technology teams.

• Strong communication and storytelling skills.
• Ability to synthesize complex ideas into clear, structured narratives.
• Experience developing executive-level presentations.
• Strong project management and organizational skills.
• Strong ability to manage multiple priorities, timelines, and stakeholders.
• Detail-oriented with a proactive, follow-through mindset.
• Analytical and financial acumen.
• Ability to structure problems and analyze data to generate insights.
• Familiarity with business cases, ROI, and financial modeling.
• Research and structured thinking skills.
• Ability to conduct market research and translate findings into actionable insights.

• Understanding of the insurance value chain, including underwriting, pricing, claims, and related areas.
• Specialty or commercial lines experience.