Product Leader
John Cornelius McCaskill
Transforming complex products, platforms, and customer experiences.
Product leader with 10+ years leading digital transformation across enterprise platforms, customer experiences, data, AI, and automation. I turn complex systems and customer problems into scalable products that improve growth, efficiency, reliability, and customer outcomes.
Core Strengths
What I Do
I lead complex digital and platform transformations, turning fragmented systems, customer friction, and operational constraints into scalable products that drive measurable business outcomes.
Digital Product Transformation
Modernized customer-facing digital experiences across web and mobile, simplifying complex journeys and connecting product improvements to growth, retention, and operational performance.
Enterprise Platforms & Modernization
Led modernization of complex enterprise platforms, connecting legacy systems, APIs, data, and digital experiences while establishing scalable foundations for future growth.
Customer Experience & Growth
Used behavioral data, analytics, and customer insight to identify friction, redesign journeys, personalize experiences, and improve conversion, engagement, and customer outcomes.
AI, Data & Automation
Applied AI, real-time data, analytics, and automation to improve reliability, detect operational issues, eliminate manual work, and enable faster, better-informed decisions.
Product Leadership & Operating Systems
Built the structures that help product organizations perform strategy, roadmaps, prioritization, metrics, governance, team development, and cross-functional execution.
Experience Highlights
Selected Experience
Highlights from product leadership roles across banking, lending, enterprise customer communications, and digital products.
Enterprise Platform Transformation
Led modernization of an enterprise platform, introducing AI capabilities, real-time data integration, and operational visibility across 100+ million annual customer interactions.
Digital Experience & Growth Transformation
Led transformation across mobile, web, servicing, and customer engagement, connecting customer experience, data, personalization, and automation to measurable growth and operational outcomes.
Product & Platform Transformation
Led four product areas while establishing product operating practices, performance measurement, customer journey disciplines, and the foundation for legacy modernization.
Building a 0→1 Customer Platform
Built and launched a customer loyalty platform from concept to market.
Career Journey
Professional Experience
Over the past decade, I've led product transformations across complex enterprise environments, modernizing platforms, improving customer experiences, building product organizations, and connecting technology investments to measurable business outcomes.
VP, Product
Citizens Bank • 2025 – 2026
- Led product strategy and modernization for an enterprise customer engagement ecosystem delivering 378MM+ customer messages annually aligning platform investments with customer experience, operational performance, and enterprise priorities.
- Mapped a fragmented ecosystem of platforms, integrations, data flows, and ownership to establish architectural visibility and identify reliability and modernization opportunities.
- Introduced AI-enabled monitoring and anomaly detection to surface missing feeds, duplicate activity, and delivery failures earlier, shifting teams from reactive incident discovery toward proactive platform management.
- Advanced real-time data integration and event-driven capabilities to enable faster, more relevant customer interactions across digital channels.
- Led cross-functional execution across Engineering, Architecture, Data, Marketing, Operations, Risk, and executive stakeholders while guiding product managers across interconnected initiatives.
Senior Manager, Digital Product Management
Sallie Mae • 2022 – 2025
- Led digital transformation across mobile, web, servicing, and customer engagement, using behavioral analytics and customer insight to identify friction and prioritize high-impact improvements.
- Redesigned the mobile payment journey from 7 steps to 3, simplifying repayment to Pay → Select Amount → Confirm and contributing to improvement in the app's rating from 3.2 to 4.5.
- Built analytics into the mobile experience and used behavioral signals to redesign delinquent servicing, reducing inbound calls by 50% while recovering approximately $2M in delinquent payments.
- Led modernization of SallieMae.com onto Adobe Experience Manager, establishing reusable content architecture, governance, analytics integration, and scalable digital publishing capabilities.
- Integrated Salesforce and Zeta to connect customer data, behavioral signals, personalization, and event-driven engagement, generating $1.7MM in annual savings while eliminating significant manual engineering work.
- Replaced batch-oriented application follow-up with event-driven automation that contacted customers within 15–30 minutes of abandonment, achieving a 25% recovery rate and approximately $590K–$780K in incremental funded loan volume.
Senior Digital Product Manager
Nelnet • 2021 – 2022
- Led four product areas spanning web/mobile, APIs & integrations, data analytics, and core platform infrastructure while helping establish a stronger product management discipline across the organization.
- Built foundational product operating practices across strategy, roadmapping, discovery, requirements, prioritization, refinement, success criteria, and delivery while coaching PMs and Product Owners on consistent execution.
- Introduced customer journey mapping and story mapping to help teams understand end-to-end user behavior, identify friction, and connect product development to customer problems rather than feature requests.
- Created a Power BI performance framework spanning 40+ teams, providing visibility into work in progress, throughput, lead time, defects, and system performance to replace intuition-driven delivery with measurable operating signals.
- Led discovery and requirements for legacy modernization, mapping systems, dependencies, data, integrations, and technical constraints to establish the foundation for migration toward a modern digital architecture.
- Developed an automated content-governance capability that identified inactive enterprise documentation for archival and deletion, reducing manual administration and projecting approximately $200K in annual savings.
Founder & Director, Product
Rewardance • 2016 – 2020
- Founded and led development of a 0 → 1 customer loyalty platform, taking the product from problem discovery and concept through strategy, design, development, launch, and market adoption.
- Built personalized engagement and loyalty capabilities that increased customer lifetime value by 30%, using customer behavior and performance data to guide product decisions.
- Owned the full product lifecycle across customer discovery, prioritization, UX, technology, go-to-market, measurement, and iteration while balancing customer needs with commercial viability.
- Built firsthand understanding of product economics and entrepreneurship by making decisions across product, customer acquisition, operations, technology, and business strategy rather than optimizing a single product function.
Leadership Philosophy
How I Lead
My approach to product leadership is grounded in clarity, measurable outcomes, customer empathy, and cross-functional alignment.
Start with the Customer
Great products begin with a deep understanding of customer problems, not assumptions.
Measure Outcomes
Success isn't measured by features shipped. It's measured by customer and business impact.
Simplify Complexity
The best products hide complexity and create intuitive experiences for customers and internal teams.
Lead Through Alignment
Product leaders succeed by bringing engineering, design, operations, and business partners together.
Never Stop Learning
Every launch creates new insights. The best teams continuously learn, adapt, and improve.
Credentials
Education & Certifications
Continuous learning has been a constant throughout my career, combining formal education with agile and product leadership certifications.
Master of Business Administration
Information Technology Management
Western Governors University
Professional Scrum Product Owner II
PSPO II
SAFe Agile Product Manager
APM
SAFe Product Owner / Product Manager
POPM
Crystal Training
Advanced Product Management