Director, Digital Acquisition

Jobtailor; Webster (MA); On-site; USD 150,000 - 190,000; Full time

Job summary

Jobtailor in Massachusetts is seeking a senior funnel optimization leader to own and transform the acquisition funnel across leads, quotes, and bind conversion. You will define a strategy, drive AI-driven insights, and collaborate with product, pricing, IT, and analytics to accelerate growth.

The role emphasizes AI/ML applications, experimentation, dashboards, and performance reporting. You will lead cross-functional teams, optimize the digital quote experience, and ensure ROI through

Qualifications

• 7+ years of experience in insurance, digital acquisition, or funnel optimization.
• Experience optimizing end-to-end customer acquisition journeys.
• Experience leveraging AI, predictive analytics, or automation tools.
• Strong understanding of insurance quoting processes and underwriting.
• Deep experience with A/B testing and data-driven optimization.
• Familiarity with AI/ML applications in marketing or conversion optimization.
• Strategic thinker who can translate vision into execution.
• Ability to influence cross-functional stakeholders.
• Strong analytical, problem-solving, and communication skills.

Responsibilities

• Own & Transform the Acquisition Funnel.
• Lead end-to-end acquisition funnel, including leads, quote experience, and bind conversion.
• Define and execute a funnel optimization strategy aligned with growth and profitability objectives.
• Leverage AI-driven insights and predictive analytics to uncover new conversion opportunities.
• Establish and manage KPIs, performance metrics, and optimization frameworks.
• Design and continuously improve a best-in-class digital quote experience.
• Identify friction points and streamline the customer journey across touchpoints.
• Use AI-powered personalization to tailor quote pathways and enhance user engagement.
• Lead A/B testing and experimentation programs to continuously improve performance.
• Utilize AI tools to accelerate testing cycles and predict outcomes.
• Champion the adoption of AI and machine learning solutions to enhance targeting, personalization, and funnel performance.
• Collaborate across Product, Pricing, IT, State Management, and Data & Analytics.
• Own and evolve the fraud prevention strategy across leads and quotes.
• Develop and manage dashboards, reporting tools, and performance insights.

Skills

Analytical thinking

Problem solving

Communication

Cross-functional collaboration

Strategic thinking

Leadership

Job description

Responsibilities

• Own & Transform the Acquisition Funnel
• Lead the end-to-end acquisition funnel, including leads, quote experience, and bind conversion
• Define and execute a funnel optimization strategy aligned with growth and profitability objectives
• Leverage AI-driven insights and predictive analytics to uncover new conversion opportunities
• Establish and manage KPIs, performance metrics, and optimization frameworks
• Design and continuously improve a best-in‑class digital quote experience
• Identify friction points and streamline the customer journey across touchpoints
• Use AI-powered personalization to tailor quote pathways and enhance user engagement
• Lead A/B testing and experimentation programs to continuously improve performance
• Utilize AI tools to accelerate testing cycles and predict outcomes
• Champion the adoption of AI and machine learning solutions to enhance targeting, personalization, and funnel performance
• Collaborate across Product, Pricing, IT, State Management, and Data & Analytics
• Own and evolve the fraud prevention strategy across leads and quotes
• Develop and manage dashboards, reporting tools, and performance insights

Requirements

• 7+ years of experience in insurance, digital acquisition, or funnel optimization
• Demonstrated success optimizing end-to-end customer acquisition journeys
• Experience leveraging AI, predictive analytics, or automation tools in a business context
• Strong understanding of insurance quoting processes and underwriting principles
• Deep experience with A/B testing, experimentation frameworks, and data-driven optimization
• Familiarity with AI/ML applications in marketing, digital experience, or conversion optimization
• Strategic thinker with the ability to translate vision into execution
• Proven ability to influence and align cross-functional stakeholders
• Strong analytical, problem-solving, and communication skills