Resume

Charles Weiss

Product and Technology Executive | CTO | VP Engineering | VP Product Development

Montreal, Quebec

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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

2023 - Present

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

2021 - 2023

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

2016 - 2021

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

2007 - 2016

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.