Director Digital Monetization Jobs (NOW HIRING)

Our client is a highly respected organization with a diversified investment portfolio across real estate, media, customer experience, and infrastructure sectors. Headquartered in San Juan, Puerto Rico, and with operations throughout the United States and Latin America, the company has built a strong reputation for driving value creation, strategic growth, and long-term investment success. Its achievements are supported by a talented, innovative, and highly engaged workforce committed to excellence.

As part of its ongoing growth strategy and digital transformation initiatives, the organization is seeking a Director, Digital Solutions & Technology Development. This executive leadership role will be responsible for driving the company's digital innovation agenda, advancing technology capabilities, and leading the development of scalable digital solutions that enhance business performance, customer engagement, and long-term competitive advantage.

Responsible for leading the strategy, development, optimization, and performance of the Company’s consumer-facing digital product ecosystem. This role is accountable for the digital subscription infrastructure, product platform roadmap, application experience, e-commerce monetization capabilities, audio and video product experience, and data-driven personalization strategy. The position connects audience behavior, product innovation, subscription growth, digital monetization, user experience, and business strategy to drive revenue growth, user engagement, retention, and long-term customer value.

The position works closely with the Commercial, Marketing, Editorial, Data, Product, Technology, Operations, and Executive Leadership teams to ensure that digital initiatives are aligned with strategic priorities and overall business objectives.

• Lead the strategy, configuration, and optimization of the Piano platform to support digital subscriptions, premium paywalls, user gating, and subscriber lifecycle management.
• Own the subscription product roadmap to increase conversion, retention, engagement, renewal performance, and customer lifetime value.
• Develop monetization strategies for ad‑free tiers, premium content bundles, partner subscriptions, newsletters, digital offers, and audience revenue opportunities.
• Oversee the performance and continuous improvement of consumer‑facing digital products, including websites, mobile apps, newsletters, audio, video, and OTT/Smart TV experiences.
• Prioritize product enhancements, user experience improvements, feature releases, and platform initiatives based on audience needs, business impact, and revenue potential.
• Lead the optimization of digital commerce experiences, including subscription purchases, checkout flows, payment journeys, promotional offers, and transaction conversion.
• Identify opportunities to reduce funnel friction through simplified checkout, digital wallets, alternative payment methods, and improved billing experiences.
• Monitor audience behavior, product performance, subscription metrics, churn indicators, engagement trends, and revenue data to identify risks and growth opportunities.
• Lead the strategy for personalization, recommendation systems, audience intelligence, and AI‑enabled product experiences.
• Identify AI and automation use cases that improve content discovery, metadata tagging, transcription, translation, audience segmentation, and workflow efficiency.
• Translate audience, product, subscription, and revenue insights into actionable recommendations for Product, Editorial, Marketing, Commercial, and Executive Leadership.
• Build and manage the digital product and monetization roadmap across subscriptions, platforms, apps, e-commerce, audio, video, data, and AI‑enabled experiences.
• Align cross‑functional stakeholders around priorities, timelines, ownership, success metrics, and launch readiness for major digital product initiatives.
• Manage external vendors and strategic partners related to subscription platforms, product tools, media solutions, commerce capabilities, analytics, and digital monetization.
• Present product performance, monetization opportunities, risks, progress, and recommendations to executive leadership.
• Stay current on trends in digital media, subscriptions, audience monetization, personalization, AI, streaming, mobile apps, and digital commerce.
• Comply fully and consistently with the Company's standards, policies, and procedures and the local and federal laws applicable to our industry, business, and employment practices.
• May perform other duties and responsibilities as assigned, in accordance with the education and experience requirements contained in this document.

• Bachelor's degree in Business Administration, Marketing, Digital Media, Product Management, Communications, Data Analytics, Technology Management, Innovation, or a related field. Master’s degree in Business Administration, Digital Strategy, Product Management, Innovation, Marketing, Data Analytics, or a related field preferred.
• 8+ years of progressive experience in digital product strategy, subscription products, digital monetization, media platforms, e-commerce, audience development, product management, digital transformation, or related fields. 5+ years of leadership experience managing cross‑functional digital initiatives, product portfolios, monetization programs, subscription growth initiatives, or digital business transformation efforts.
• Experience in media, publishing, streaming, subscriptions, digital commerce, audience revenue, or consumer digital products strongly preferred.
• Experience with subscription management platforms such as Piano or similar digital subscription, paywall, or customer lifecycle platforms.
• Strong digital product management capabilities, including roadmap development, prioritization, user experience optimization, stakeholder alignment, and performance measurement.
• Understanding of digital media business models, including subscriptions, advertising, branded content, premium content, newsletters, podcasts, video, OTT, e‑commerce, and partner monetization.
• Ability to connect audience behavior, product performance, content strategy, and revenue opportunities into actionable business recommendations.
• Experience improving digital checkout flows, subscription conversion funnels, payment journeys, billing experiences, and customer retention processes.