Director, Digital Growth Strategy; Hybrid - Webster or Boston

Summary

The Director, Digital Growth Strategy is a strategic, data-driven leader responsible for driving scalable, profitable customer acquisition across paid and targeted digital marketing channels. This role owns end-to-end performance marketing— from channel strategy and media optimization to experimentation, AI-enabled insights, and growth scaling. You will play a critical role in accelerating growth by combining analytical rigor, creative innovation, and strong leadership capabilities.

This position is ideal for someone passionate about leveraging AI to enhance decision‑making, personalization, and marketing efficiency within a competitive and regulated insurance environment.

• Develop and execute a comprehensive, data‑driven growth marketing strategy aligned with business and revenue goals
• Identify and prioritize high‑impact opportunities to scale profitable growth across acquisition channels
• Integrate AI‑driven insights and predictive analytics to improve targeting and conversion outcomes
• Own and optimize the full marketing funnel—from awareness through conversion

• Oversee all paid media channels, including paid search, paid social, display, programmatic, affiliate, and emerging platforms
• Leverage AI‑based tools and automation (e.g., bid optimization, audience modeling, budget allocation) to maximize performance
• Manage agency partners and/or internal teams, ensuring accountability for results, innovation, and ROI
• Continuously optimize media spend using data, attribution models, and AI‑driven recommendations

• Improve key acquisition metrics, including CAC, conversion rates, and LTV/CAC ratio
• Utilize advanced analytics and AI‑powered segmentation to enhance targeting and personalization
• Partner with Analytics and Product teams to implement enhanced tracking, predictive modeling, and marketing intelligence capabilities

• Lead a structured experimentation roadmap across creative, messaging, audience, and landing pages
• Incorporate AI tools to accelerate testing cycles (e.g., automated creative testing, dynamic content generation, performance prediction)
• Build scalable frameworks to turn test results into repeatable growth strategies
• Foster a strong test‑and‑learn culture supported by data and machine‑learning insights

• Partner with creative teams to develop high‑performing, data‑informed ad creatives
• Use AI‑driven tools to generate, test, and optimize creative assets and messaging at scale
• Drive cross‑channel personalization strategies to improve engagement and conversion

• Identify, validate, and scale high‑performing campaigns while maintaining profitability targets
• Apply AI‑enabled forecasting and scenario modeling to inform investment decisions and growth planning
• Balance aggressive growth goals with disciplined financial management and ROI accountability

• Lead, mentor, and develop a high‑performing growth marketing team
• Act as a thought leader in AI adoption, driving best practices and upskilling across the organization
• Collaborate with Product, IT, Data, Compliance, and Finance teams to implement AI capabilities responsibly
• Ensure all marketing activities comply with insurance industry regulations

• 7+ years of experience in digital, growth, or performance marketing
• Proven success scaling customer acquisition through paid media and targeted marketing channels
• Demonstrated experience leveraging AI, automation, or advanced analytics to improve marketing performance
• Strong expertise with performance marketing platforms (e.g., Google Ads, Meta, programmatic platforms)
• Experience designing and executing A/B testing and experimentation frameworks
• Background in the insurance industry or another highly regulated environment
• Leadership experience, including team management or strong cross‑functional influence

• Experience with AI‑powered marketing tools (e.g., predictive analytics,…