Director Of Media

About The Role

DMS is seeking a strategic, data-driven Director of Media to own paid media strategy and execution for our insurance lead generation business. This leader will drive full-funnel media strategy, performance optimization, media buying, partner management  and budget allocation to deliver scalable, compliant and profitable lead acquisition at scale.

The ideal candidate brings deep expertise in high-volume performance marketing, hands-on experience in regulated industries (insurance strongly preferred), and a proven track record of scaling customer acquisition while maintaining strong unit economics - CPL, CAC, LTV and ROAS. You understand P&C insurance lead gen economics including quote rate, bind rate and carrier partner standards, and you know how to optimize all the way through the funnel, not just the top product capabilities.

Why Join DMS?

DMS is in an exciting phase of growth and transformation within its insurance vertical. As the Director of Media, you will have meaningful authority and visibility, owning the full media function, shaping channel strategy and operating as a key partner to the GM and executive leadership team.

This is a high-impact opportunity to build and optimize a performance marketing engine in one of the most analytically rigorous verticals in digital media. If you are energized by connecting media performance to real business outcomes, this role is built for you.

Compensation Overview: The anticipated annual base salary range for this position is $185,000–$195,000. In addition, this role is eligible for up to 20% annual incentive compensation based on individual and business performance. Actual compensation may vary based on work experience, education and skill level.

Job Type: Full-Time, Salary, Exempt

Location: US Remote (AL,AZ,CA,CO,CT,DC,FL,GA,ID,IL,IN,MA,MD,MI,MO,NC,NH,NJ,NV,NY,OH,PA,RI,TN,TX,UT,VA,WA,WI)

Key Responsibilities:

Strategic Leadership

• Own end-to-end paid media strategy across all digital channels for the P&C insurance vertical
• Develop scalable acquisition strategies to grow high-intent P&C insurance leads profitably
• Set performance targets aligned with revenue, margin and growth goals in partnership with the GM
• Partner with executive leadership on annual and quarterly forecasting and media budget planning
• Leverage data-driven insights and customer research to continuously refine messaging and measure business impact
• Serve as the internal authority on paid media for P&C — educating stakeholders, advocating for investment and connecting media strategy to business outcomes

• Own and optimize performance across all paid channels, including:
• Paid Search — Google Ads, Microsoft/Bing Ads
• Paid Social — Meta, TikTok, LinkedIn, Pinterest
• Programmatic & Display — DSPs, RTB, audience targeting at scale
• Native Advertising — Taboola, Outbrain and similar platforms
• Affiliate & Lead Aggregator Partnerships — including insurance marketplaces (e.g., EverQuote, MediaAlpha, Assurance IQ ecosystem)
• Email & CRM-driven acquisition programs
• Evaluate and test emerging channels to diversify acquisition and reduce platform concentration risk
• Manage channel mix strategy with a clear view of diminishing returns and incremental opportunity

Performance & Optimization

• Drive continuous improvement of CPL, CPA, ROAS, quote rate, bind rate and lead quality metrics
• Implement rigorous A/B testing frameworks across creative, landing pages, audience targeting and offer structures
• Optimize toward qualified, bindable leads — not just volume
• Partner with analytics and BI teams on attribution modeling, incrementality testing and media mix modeling
• Build and maintain dashboards and reporting cadences that connect media activity to downstream revenue outcomes

Compliance & Regulatory Management

• Ensure all media buying practices adhere to TCPA, CAN-SPAM and state-by-state P&C insurance advertising regulations
• Implement consent capture and data handling workflows compliant with CCPA and applicable privacy laws
• Partner with Legal and Compliance to vet new channels, creative and targeting approaches before launch
• Maintain platform account health standards across all ad networks to protect business continuity
• Stay current on regulatory changes affecting insurance lead generation and performance marketing

Lead Quality & Revenue Alignment

• Collaborate with Sales, Carrier Partnerships and Operations to ensure leads meet underwriting and conversion standards
• Own the feedback loop between media buying and downstream performance — quote rate, bind rate, policy revenue and LTV
• Optimize campaigns based on close rate and long-term customer value, not just top-funnel cost metrics
• Partner with carriers and distribution partners on lead quality standards and volume commitments
• Build reporting that connects media investment to policy bind economics and margin contribution

AI & Technology Enablement

• Champion AI tool adoption for accelerated campaign optimization, creative testing, and audience modeling
• Leverage AI-powered bidding and automation tools to improve efficiency across paid channels
• Use predictive analytics and machine learning tools for lead quality scoring and media mix optimization
• Explore AI applications for creative generation, landing page personalization and incrementality measurement
• Enable the broader marketing team to adopt AI tools effectively through best practices and knowledge sharing
• Stay current on emerging AI/ML capabilities relevant to performance marketing and insurance vertical dynamics

Vendor & Partner Management

• Manage relationships with media platforms, agencies, DSPs, data providers and affiliate partners
• Evaluate and maintain the MarTech stack — attribution platforms, CRM integrations, ad tech and analytics tools
• Optimize vendor spend and ensure all partners are held to clear performance SLAs

Team Leadership & Development

• Lead, mentor, and grow a team of performance marketing individual contributors and team leads
• Foster a culture of analytical rigor, accountability and continuous optimization
• Establish clear KPIs, OKRs and performance expectations for the media team
• Collaborate cross-functionally with Product, Sales, Analytics and Customer Success to deliver cohesive end-to-end performance
• Build team capabilities in emerging areas including programmatic, AI-assisted optimization and compliance-aware buying

Required Qualifications:

Experience

• 7+ years in performance marketing, paid media or digital acquisition roles
• 3+ years in a media leadership position managing teams and significant media budgets ($5M+ annually)
• Proven track record scaling customer acquisition in regulated or compliance-sensitive industries (insurance, fintech or healthcare strongly preferred)
• Deep hands-on experience across paid search and at least two additional paid channels (social, programmatic, native or affiliate)
• Direct experience with P&C insurance lead generation, insurance aggregator ecosystems or similar performance lead gen businesses preferred
• Experience managing full-funnel optimization from CPL through bind rate or equivalent downstream revenue metric
  

 Technical & Platform Skills 

• Paid Search: Google Ads, Microsoft Advertising — campaign architecture, bidding strategy, Quality Score optimization
• Paid Social: Meta Ads Manager, TikTok Ads, LinkedIn Campaign Manager
• Programmatic: DSP experience (DV360, The Trade Desk, or equivalent)
• Attribution & Measurement: Northbeam, Rockerbox, Triple Whale, Google Analytics or equivalent multi-touch attribution tools
• Analytics & BI: Strong SQL fluency or comfort working with analysts; Tableau, Looker or similar BI tools
• CRM & Marketing Automation: Salesforce, HubSpot or equivalent
• Lead Management: Experience with lead distribution platforms, ping-post systems or lead marketplace operations

Leadership & Soft Skills

• Strong communication skills with the ability to translate media performance into business and financial language for executive audiences
• Proven ability to influence cross-functional stakeholders and drive alignment across sales, ops, product and analytics
• Analytical mindset with a bias toward data-driven decision-making and structured experimentation
• Comfort operating in a PE-backed, metrics-driven environment with high accountability to business outcomes
• Experience managing and developing high-performance marketing teams

Preferred Qualifications:

• Direct P&C insurance experience - auto, home, renters or commercial lines lead generation
• Familiarity with carrier partner economics, underwriting standards and insurance distribution models
• Experience working within or alongside insurance aggregator platforms (EverQuote, MediaAlpha, GoHealth or similar)
• Working knowledge of TCPA compliance, insurance advertising regulations, and state-level compliance requirements
• Experience with FinOps or media budget optimization practices in high-spend environments
• Active user of AI-assisted marketing tools for bidding automation, creative testing or predictive analytics
• Background in CRO, landing page optimization and funnel experimentation
• Experience building or scaling a media function from early-stage through significant growth
  

Benefits Available To Eligible Employees Include The Following:

• Medical, dental, vision insurance
• Wellness and mental health benefits
• Tax-Advantaged healthcare accounts
• Financial and income protection benefits (life insurance, short-term disability, 401(k)
• Paid time off (PTO), holidays and sick time off
• Remote worker assistance for wellness and home office

Candidates will be considered in totality of their skills and experience versus strict interpretation of “requirements.”

About DMS

Digital Media Solutions is a performance-driven digital marketing company that connects consumers and brands through data, technology and proprietary media platforms. Our systems power high-volume consumer acquisition across multiple verticals, processing large-scale traffic and real-time decisioning in dynamic market environments.