[Hiring] Director Digital Customer Acquisition @Progressive Casualty Insurance Company

Role Description

As a director of digital customer acquisition, you'll change how people shop for property insurance in our direct digital journeys. You'll lead the team responsible for our online property quote-to-purchase experience, with accountability for:

• Digital customer acquisition
• Conversion
• Revenue growth

You'll use customer behavior, experimentation, market trends, and competitive insights to shape a differentiated product vision and strategy that fuels growth. Working with business, technology, design, and data partners, you'll turn that strategy into a clear roadmap and lead your team in defining, testing, and scaling technology-enabled experiences. As a leader, you'll champion continuous in-market learning and a product mindset focused on reusable, scalable capabilities.

Location: You'll work remotely, and travel based on business needs.

Qualifications

• A minimum of 13 years of related professional work experience (e.g., definition and delivery of products through digital, voice, and agent channel experiences) and at least 5 years of leadership experience (e.g., directly managing or mentoring).
• {OR} Bachelor's degree or higher and a minimum of 10 years of related professional work experience (e.g., definition and delivery of products through digital, voice, and agent channel experiences) and at least 5 years of leadership experience (e.g., directly managing or mentoring).

Requirements

• Insurance or financial services experience
• Experience building and developing high-performing product teams in discovery and delivery, leading through leaders, and operating as a player-coach
• Experience leading digital customer acquisition portfolios, applying agentic AI to customer or agent experiences, and/or owning agent-led sales experiences
• A track record of building business cases, making investment trade-offs, and delivering measurable revenue and conversion results, plus experience shaping technology capabilities and platform integrations with engineering partners
• A proven test-and-learn approach that uses experiments and data to decide what to scale, plus experience managing SaaS platforms, vendors, and/or carrier partners

Benefits

• 401(k) with dollar-for-dollar company match up to 6%
• Medical, dental & vision, including free preventative care
• Wellness & mental health programs
• Health care flexible spending accounts, health savings accounts, & life insurance
• Paid time off, including volunteer time off
• Paid & unpaid sick leave where applicable, as well as short & long-term disability
• Parental & family leave; military leave & pay
• Diverse, inclusive & welcoming culture with Employee Resource Groups
• Career development & tuition assistance

Energage recognizes Progressive as a 2026 Top Workplace for: Innovation, Purposes & Values, Work-Life Flexibility, Compensation & Benefits, and Leadership.

Company Description

Equal Opportunity Employer

Applicants must be authorized to work for any employer in the U.S. without the need or potential need, of current or future sponsorship for employment. Progressive does not hire candidates with (e.g., F-1 CPT, OPT, or STEM OPT, H-1B, O-1, E-3, TN) statuses for this role.

For ideas about how you might be able to protect yourself from job scams, visit our scam-awareness page at https://careers.progressive.com/pages/how-we-hire-faq-job-scams/

We'll consider qualified applicants with arrest and conviction records. Note that federal law may prohibit individuals with certain felony convictions from working in the insurance industry unless they have obtained the required regulatory authorization.

#LI-Remote

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.