Head of New Business & Enablement

Job Summary

Head of New Business Experience & Enablement is responsible for defining, owning, and evolving the end-to-end new business experience for Westfield’s independent agents. This role drives the strategy, design, and continuous improvement of how new business is submitted, quoted, underwritten, and bound - across all digital and traditional channels.

Acting as the business owner for this experience, this individual will balance deep understanding of underwriting, product, pricing, operations, distribution, and marketing with design thinking and behavioral economics principles to deliver a uniquely simple and differentiated agent experience.

The Experience Owner will partner closely with IT product teams to define the roadmap, prioritize enhancements, and ensure investments in platforms like Westfield’s proprietary online rating and underwriting system drive measurable improvement in ease of doing business. This includes leveraging AI and third-party data to reduce keystrokes, accelerate quotes, and improve data quality - while maintaining underwriting integrity and profitability.

• Own the vision and strategy for the new business experience across digital, comparative rater, traditional and non-traditional submission channels.
• Align business strategy, agent needs, and technology capabilities to deliver a frictionless, intuitive quoting and underwriting experience.
• Serve as the voice of the business and advocate for the agent in all capability decisions.
• Identify, prioritize, and sequence initiatives that drive measurable improvements in agent satisfaction, conversion rates, and operational efficiency.

• Lead redesign of Westfield’s proprietary online rating and underwriting platform to simplify workflows, reduce data entry, and improve quote accuracy.
• Partner with IT and data science to implement AI-enabled automation, including document ingestion, data extraction, and pre-filled quote generation.
• Champion the use of behavioral economics and UX design principles to guide desired user behaviors and improve agent decision-making.
• Leverage third-party and internal data sources to supplement submissions, reducing manual input and improving underwriting precision.

• Collaborate with Underwriting, Product, Pricing, Sales, Marketing, and Operations to ensure a unified experience that reflects the totality of the Westfield Small Business value proposition.
• Partner with Distribution and Field teams to Gather agent insights, translate them into actionable requirements, and measure outcomes.
• Work with IT Product Owners and Scrum teams To ensure backlog prioritization reflects business impact and customer value.
• Define and track experience KPIs (e.g., ease of doing business, submission-to-quote speed, quote-to-bind ratio, agent NPS).

• Lead assessment of the comparative rater and aggregator landscape, defining Westfield’s participation strategy and competitive positioning.
• Continuously scan the market for emerging technologies, platforms, and data partnerships that can enhance the agent experience and support profitable growth.

• Serve as a change champion, driving adoption of new tools and behaviors among internal teams and distribution partners.
• Communicate the vision, progress, and impact of experience improvements across the organization and to executive leadership.
• Represent the new business experience domain in cross-enterprise initiatives, ensuring alignment to Westfield small business strategy.

• 7+ years of experience in small commercial insurance, with a strong understanding of underwriting, product development, pricing, and distribution.
• Proved track record of leading experience transformation or digital enablement initiatives within insurance or financial services.
• Bachelor’s degree In business, marketing, economics, or related field (MBA or advanced degree preferred).
• Familiarity with agile product delivery and ability to partner effectively with IT product owners and delivery teams.
• Working knowledge of AI/automation applications and data-driven…