Senior Director, Digital Experience & AI

Location: On-site in Chicago, Illinois, United States

Salary: $235,620–$318,780 base compensation per year

Company

hirify.global is a global fintech company providing insurance, reinsurance, payroll, benefits, cybersecurity, mortgage, and related business solutions.

What you will do

• Define and execute the enterprise digital experience vision, strategy, and roadmap across digital channels.
• Own the web ecosystem, digital platforms, governance, performance, personalization, conversion optimization, and customer journey initiatives.
• Lead AI transformation across Marketing by developing AI-powered tools, workflows, use cases, enablement programs, and governance practices.
• Direct enterprise SEO and AEO strategy, including content optimization, structured data, organic growth measurement, and AI-driven discoverability.
• Use analytics, customer insights, and performance metrics to improve engagement, conversion, customer acquisition, operational efficiency, and revenue growth.
• Build and lead the Digital Experience organization, including recruiting, talent development, operating models, vendor partnerships, and cross-functional collaboration.

Requirements

• 15+ years of experience in digital experience, digital strategy, customer experience, digital product, or digital marketing leadership.
• Proven experience building and scaling enterprise digital programs, high-performing teams, digital platforms, and large-scale website transformations.
• Strong knowledge of SEO, content optimization, structured data, AI-driven search environments, AI technologies, and large language models.
• Experience using analytics, data, and customer insights for strategic decision-making.
• Ability to influence executive stakeholders and lead cross-functional initiatives across Product, Engineering, Data, Revenue, Technology, Legal, and Compliance.
• Comfort with an on-site presence in Chicago is required to support collaboration, team leadership, and cross-functional partnership.

Nice to have

• Experience in fintech, financial services, insurance, or other complex regulated industries.

Culture & Benefits

• Medical, dental, vision, life, and disability insurance.
• Paid time off, holidays, sick time, maternity and paternity leave, and an Employee Assistance Program.
• 401(k) with immediate vesting, HSA and FSA options, commuter benefits, and employee discounts.
• Fertility benefits, wellness resources, Calm app subscription, legal plan options, and pet insurance.
• Work culture centered on leadership, accountability, collaboration, innovation, experimentation, and continuous learning.