Insurance In Bermuda Jobs in Virginia (NOW HIRING)

This is a 6 month contract-to-hire and needs to meet Client full-time conversion policies. Those dependent on a work permit sponsor now or anytime in the future (ie H1B, OPT, CPT, etc) do not meet Client requirements for this opening.

**MUST BE HYBRID in Richmond, VA

**MUST BE W2; No Corp-to-Corp**

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

This team is responsible for developing our client's 3-5 year technology and capability roadmap across our US and Bermuda insurance businesses. We operate at the intersection of business strategy, technology, and transformation, ensuring that investments are aligned to growth, profitability, and operational efficiency goals.

As a Strategy Associate, you will play a key role in supporting enterprise-wide strategic initiatives combining the structured problem solving of a management consultant, the coordination and execution rigor of a project manager, and the curiosity and analytical depth of a research analyst.

This is a high-visibility role that interacts directly with senior business and technology leaders and contributes to critical decisions on investment priorities, transformation sequencing, and capability development.

What You ll Do

• Support Business Strategy Discovery by planning and coordinating sessions with business, technology and other key stakeholders
• 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
• 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.
• 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
• Collaborate with business, technology and finance stakeholders to develop business cases/CBAs and support financial analyses of technology investments
• Translate findings into concise, business-friendly recommendations and develop clear, executive-ready PowerPoint presentations
• Assist in building and maintaining multi-year technology and capability roadmaps, consolidating views across business units ,and surfacing cross-functional dependencies

Experience

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

Core Skills

• Strong Communication & Storytelling
• Ability to synthesize complex ideas into clear, structured narratives
• Experience developing executive-level presentations
• Project Management & Organization
• Strong ability to manage multiple priorities, timelines, and stakeholders
• Detail-oriented with a proactive, follow-through mindset
• Analytical & Financial Acumen
• Ability to structure problems and analyze data to generate insights
• Familiarity with business cases, ROI, and financial modeling
• Research & Structured Thinking
• Ability to conduct market research and translate findings into actionable insights
• Insurance Knowledge
• Understanding of insurance value chain (underwriting, pricing, claims, etc.) preferred
• Specialty or commercial lines experience is a plus