Resume
Charles Weiss
Product and Technology Executive | CTO | VP Engineering | VP Product Development
Executive Profile
Product and technology executive with 25+ years of experience building, scaling, and modernizing online platforms across payments, billing, acquisition, conversion, retention, and high-volume SaaS systems. Proven record leading product development, engineering, architecture, and delivery organizations through growth, transformation, and platform evolution. Known for combining strategic product vision, deep technical fluency, data-informed decision making, and disciplined execution to turn complex opportunities into measurable business outcomes.
Executive Strengths
- Product and Technology Strategy
- Engineering Leadership
- Platform Modernization
- AI-Enabled Delivery
- Payments and Billing Systems
- SaaS Platforms
- Cloud and Infrastructure Optimization
- Progressive Delivery
- Data-Informed Product Development
- Organizational Transformation
- Compliance and Security Enablement
- Executive Stakeholder Alignment
Experience
Vice President of Product Development / Vice President of Engineering
Revaly, formerly FlexPay
Lead product development, engineering, architecture, and delivery for a fintech platform focused on payment performance, approval optimization, and recovery. Own the operating model connecting product strategy, technical execution, platform reliability, and measurable business outcomes.
- Built Revaly's Trust Network from concept to launch, creating a secure data exchange between financial institutions, fraud detection platforms, orchestrators, and merchants that reduced false fraud declines by 115 bps.
- Introduced Upfront Approval Optimization, expanding Revaly's value proposition earlier in the payment lifecycle by preventing false declines before recovery and increasing approvals by 50 bps.
- Rebuilt Product Development into an AI-enabled execution organization, making AI usage a standard operating expectation and increasing product engineering throughput by 400%.
- Unified Product and Engineering under a full-lifecycle operating model spanning planning, delivery, operations, measurement, and product sunset.
- Increased transaction approval performance by 2 percentage points through product KPIs, strategic roadmaps, and prioritization of high-impact initiatives.
- Accelerated release frequency from bi-monthly releases to multiple deployments per day by restructuring teams into domain-focused squads and implementing DORA, SPACE, and developer experience metrics.
- Reduced legal and compliance review time by 75% through automation of redlining, documentation, and review workflows.
- Strengthened regulatory, funding, and partner posture through leadership of SRED, IRAP, and Microsoft Unicorn Program initiatives.
Senior Director of Product Development
MavTek Inc
Led product development and engineering execution across multiple product domains for a high-scale online platform business. Directed 13 teams and 55 software engineers while aligning technology delivery with business strategy, growth, reliability, and cost efficiency.
- Led 13 teams and 55 software engineers across multiple product domains, improving alignment between engineering execution and business outcomes.
- Increased North Star metrics by 20% year-over-year by aligning roadmap execution with strategic growth priorities.
- Drove a 25% lift in organic search traffic through technical SEO, platform performance improvements, and cross-functional prioritization.
- Reduced infrastructure costs by 60% through architectural streamlining, tooling consolidation, and cloud optimization.
- Elevated DORA metrics to Elite levels by introducing Progressive Delivery practices and improving release discipline.
- Strengthened delivery visibility and operational accountability across product, engineering, and executive stakeholders.
Director of Technology
4th Whale Marketing
Served as the senior technology leader for a high-volume digital media and marketing platform business. Owned technology strategy, engineering leadership, platform architecture, delivery practices, and acquisition integration.
- Contributed to 15% year-over-year revenue growth by shaping and executing company technology strategy.
- Scaled the engineering organization from inception to 20 high-performing developers.
- Consolidated and integrated multiple high-traffic website acquisitions into a cohesive portfolio generating 30M+ daily sessions.
- Improved mobile performance, contributing to a 20% increase in organic search traffic.
- Led platform architecture, delivery processes, and technical operations across a complex portfolio of high-volume web properties.
Lead Software Engineer
Ex-Situ Marketing
Led software delivery, cloud migration, observability, and conversion optimization for subscription-based online platforms.
- Migrated infrastructure to AWS and implemented observability practices, achieving 99.99% uptime.
- Established data-driven product practices that increased advertising and product CTR by 20%.
- Improved conversion rates by 15% through enhanced tracking, analytics, and optimization.
- Implemented CI/CD pipelines that reduced developer feedback loops and accelerated release cycles.
- Built and operated high-volume subscription, payment, CMS, and online media platforms.
Earlier Career
Held progressive software engineering, DevOps, founder, and technical roles across web platforms, subscription billing, payment gateways, CMS systems, e-commerce, automation, data collection, and high-traffic media systems. Earlier experience includes Starmedia Communications, Fetch the Web Inc., Belmont Web Services, and IBM.