From Code to Product: How Deon Crasto Mastered Global Payments Tech
In this episode of Career Spotlight, we sit down with Deon Crasto, Principal Product Manager at Velocity Global, who shares his fascinating journey from software engineer to product management leader. With nearly a decade of experience spanning machine learning, healthcare tech, and global payments, Deon offers unique insights into navigating career transitions in the tech industry. His deep expertise in data science and AI has positioned him as a thought leader in the fintech space.
During our conversation, Deon reveals how his analytical background in data science shaped his approach to payment solutions and fraud detection. His career path includes impactful roles at OnDeck Capital, Livongo (acquired by Teladoc), and Checkr, where he developed innovative solutions for highly regulated industries. His work at OnDeck Capital revolutionized small business lending through machine learning algorithms, while at Livongo, he helped transform healthcare technology during a major acquisition. Now based in London, Deon brings a global perspective to product management and cross-border payment systems.
Deon shares candid insights about scaling products internationally and the challenges of building payment solutions that work across different regulatory frameworks. His experience leading teams through major organizational changes, including acquisitions and market expansions, provides valuable lessons for technology professionals looking to advance their careers in product management or fintech.
Key Discussion Points:
- Transitioning from software engineering to product management
- Building self-learning fraud detection models
- Managing product development in highly regulated industries
- Adapting to company acquisitions and organizational changes
- Balancing innovation with ethical AI implementation
- Navigating global payment systems and compliance
- Leading cross-functional teams and stakeholder management
- Career opportunities in financial technology
- Impact of AI on payment solutions
- Working across international markets
- Product management career progression paths
- Emerging trends in fintech and AI
Subscribe to Career Spotlight for weekly insights from technology leaders and transformation experts. Visit softwareoasis.com/subscribe to receive our bi-weekly newsletter featuring job opportunities and career resources.
During our conversation, Deon reveals how his analytical background in data science shaped his approach to payment solutions and fraud detection. His career path includes impactful roles at OnDeck Capital, Livongo (acquired by Teladoc), and Checkr, where he developed innovative solutions for highly regulated industries. His work at OnDeck Capital revolutionized small business lending through machine learning algorithms, while at Livongo, he helped transform healthcare technology during a major acquisition. Now based in London, Deon brings a global perspective to product management and cross-border payment systems.
Deon shares candid insights about scaling products internationally and the challenges of building payment solutions that work across different regulatory frameworks. His experience leading teams through major organizational changes, including acquisitions and market expansions, provides valuable lessons for technology professionals looking to advance their careers in product management or fintech.
Key Discussion Points:
- Transitioning from software engineering to product management
- Building self-learning fraud detection models
- Managing product development in highly regulated industries
- Adapting to company acquisitions and organizational changes
- Balancing innovation with ethical AI implementation
- Navigating global payment systems and compliance
- Leading cross-functional teams and stakeholder management
- Career opportunities in financial technology
- Impact of AI on payment solutions
- Working across international markets
- Product management career progression paths
- Emerging trends in fintech and AI
Subscribe to Career Spotlight for weekly insights from technology leaders and transformation experts. Visit softwareoasis.com/subscribe to receive our bi-weekly newsletter featuring job opportunities and career resources.
Creators and Guests

Host
Michael Bernzweig
Michael Bernzweig is a tech entrepreneur and podcast host. He founded Software Oasis in 1998, pioneering software distribution. Now, he connects businesses with top tech consultants and hosts the Software Spotlight, Career Spotlight, and Consulting Spotlight podcasts, providing valuable insights to professionals.

Guest
Deon Crasto
Deon Crasto is a fintech expert specializing in global payments, cross-border distribution, and AI integration in financial technology. With experience at companies like OnDeck, Livongo, Checkr, and Velocity Global, he focuses on transforming industries through real-time payment systems and regulatory compliance. His multicultural background and expertise in both startup and enterprise environments shape his perspective on financial innovation.
