Get to Know Signal Diligence

Signal Diligence is led by Jason Wolfe, a veteran Software Engineer and technology executive with nearly 30 years of industry experience across fintech, SaaS, marketplaces, and high-growth digital platforms.

Jason wrote his first program at age 10 on an 8086, launching a lifelong career defined by curiosity, exploration, and deep technical mastery. That early exposure to bulletin boards and open systems matured into a disciplined engineering career spanning enterprise environments, hyper-growth startups, and complex legacy modernizations.

Over three decades, Jason has worked across large-scale architectures and mission-critical codebases-from early work with HP and Gateway, through dozens of startups, through building and integrating products at CFAC and DealerAI, and into technical assimilation and modernization efforts with organizations such as Upwork, Snap, and Siemens.

Today, Jason is a VP of Engineering for global fintech unicorn SumUp, where he was promoted from Staff Engineer and now oversees all US systems.

Pre-Acquisition Technical Diligence Expertise

Jason has led pre-acquisition technical due diligence and post-acquisition integration planning for transactions ranging from $50M to $350M+.

His work has directly:

• Identified material technical risks early
• Exposed hidden operational and architectural liabilities
• Prevented overvaluation
• Saved acquirers millions in integration and restructuring costs
• Provided clear, investment-grade recommendations and integration roadmaps

He is known for delivering blunt, accurate, and actionable assessments that cut through narrative and get to the truth of a company's technical position.

Industry Specialties

• Fintech & Payments
• SaaS Platforms
• Marketplaces & Network-Effect Businesses
• High-Scale Distributed Systems
• Legacy Modernization & Technical Recovery

What Differentiates Signal Diligence

Hands-on engineering + executive leadership
Jason brings a rare combination of deep systems knowledge and executive-level judgment. He can read the code, interrogate the architecture, assess the team, and model the business impact.

Deep experience with both legacy and modern systems
His career spans monolithic architectures, microservices, distributed data systems, modernization efforts, and the unique complexities of older codebases that often underpin acquisition targets.

Investment-grade clarity
Stakeholders consistently cite Jason for his ability to deliver clear, unvarnished truth. No fluff. No jargon. Just accurate insight, quantified risk, and actionable strategy.