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D'Alessandro & Associates Inc.

Bridging Business & Technology

Technology Executive  ·  Product Leader  ·  Strategic Consultant

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The Bridge Between
Vision and Execution

With over two decades bridging business and technology, I've built a comprehensive understanding of both vendor and client needs across multiple sectors. From founding CTO to trusted strategic advisor, I transform complex technical challenges into business opportunities.

My strong communication, collaboration, and organizational skills have consistently earned the trust of colleagues, clients, and leadership teams across FinTech, wealth management, and enterprise technology.

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Years Experience
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Annual Marketplace Volume
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Industries Served

Core Competencies

Product & Program Management

Full lifecycle ownership from concept to deployment. Multi-year roadmaps, stakeholder alignment, and delivery excellence at enterprise scale.

IT Leadership & Architecture

High availability, low latency systems design. Engineering leadership with long-term technical vision and a focus on scalable, secure infrastructure.

Cybersecurity & Risk

Security-first methodology covering penetration testing, incident response, awareness training, and organizational cyber posture improvement.

FinTech & Trading Systems

Deep expertise in RFQ trading models, FIX protocol, pre/post trade flows, and Canada's fixed-income marketplace at multi-trillion dollar scale.

Data Platforms & Distribution

Enterprise data management, real-time price and trade data platforms, FIX-based aggregation and multi-source distribution architectures.

Business Strategy & Consulting

Cross-functional advisory spanning vendor management, BCP, operational efficiency, and strategic alignment of technology with business objectives.

Career Journey

2023 — Present

General Consulting

Technology & Cybersecurity Advisor

Strategic technology and cybersecurity advisory across organizations. Vendor agreement reviews, cyber posture improvement, BCP development, and technology platform assessments.

Prior

RBC Wealth Management

Technology Transitions Lead

Led large-scale technology transitions across thousands of users, ensuring continuity, adoption, and alignment across enterprise platforms.

Prior

CT Securities

Platform Architect

Designed and managed one of the first web-based transaction platforms with built-in compliance features — an early innovator in digital financial infrastructure.

Prior

Brokercom

Product Developer

Pioneered a communication portal between wealth management advisors and clients — an early innovator in advisor-client digital engagement.

Academic Foundation

Bachelor of Electrical Engineering Technology
Toronto Metropolitan University
(Ryerson Polytechnical Institute)
Toronto, Ontario

Interests & Passions

Motorcycles
Classic Cars
Antiques & Thrifting
Country Living
Renovation & Landscaping

Let's Connect

Open to permanent and consulting roles. Let's discuss how I can bring immediate and long-term value to your organization.