CIO Leadership Live: From Paper Checks to AI – How Deluxe Is Reinventing Itself as a Digital Payments Company
Host: Lucas Marion (Computerworld Magazine)
Guest: Yogurt Jayapakasam (Chief Technology and Digital Officer, Deluxe)
Date: March 5, 2026
Setting: CIO100 Symposium and Awards Show
Episode Overview
This episode features Yogurt Jayapakasam, Chief Technology and Digital Officer at Deluxe, discussing the company’s transformation from a legacy check-printing firm into a technology-driven payments and data solutions company. The conversation explores how Deluxe is leveraging AI, building a digital-first culture, transforming its data approach, and upskilling employees across all levels. Jayapakasam shares candid insights on the opportunities, challenges, and strategies behind Deluxe's journey into digital payments and AI-driven services.
Key Discussion Points & Insights
Deluxe’s Transformation from Checks to Tech
- Historical Shift: Deluxe’s core business was once physical check printing. Under new leadership since 2018, Deluxe clarified its strategy to pivot towards payments and data-driven technology solutions.
- Revenue Mix: As of the interview, half of Deluxe’s $2B annual revenue comes from traditional print; the other $1B is from merchant services, B2B payments, and marketing solutions post-massive technology transformation.
- Quote: “We want to pivot to becoming a payments and data company where technology becomes the product and services that we sell and not the physical paper checks…” — Yogurt Jayapakasam [01:33]
Role of AI in Deluxe’s Evolution
- AI as a ‘Force Multiplier’: Jayapakasam sees the AI revolution as the culmination of prior transformative tech waves (agile, cloud, big data).
- Quote: “I see AI's revolution now is culmination of capitalizing all the technology transformation that already took place and now they are all converging with AI.” — Yogurt Jayapakasam [02:59]
- Application Focus: Initially, AI improved cost optimization, customer support, and employee experience, but the ultimate goal is to “fundamentally reimagine everything we do inside business” [03:37].
Building a Digital-First Culture
- People Over Tech: Jayapakasam emphasizes that people and culture are more critical than technology itself in transformation.
- Quote: “Technology is the smart smaller part in my opinion. It is mostly people and culture.” — Yogurt Jayapakasam [04:19]
- Leveraging Company Roots: Deluxe’s strengths in customer commitment, service, and trust are harnessed and repositioned as drivers of digital transformation.
- Memorable Moment: Jayapakasam describes how challenging projects became easier due to employees’ deep-rooted commitment to customers [04:44].
Data, AI, and Analytics at Scale
- Platform Approach: Consolidation of siloed data into centralized platforms like Delectra Data enables company-wide visibility and actionable insights.
- Generative AI in Data Mapping: Use of large language models (LLMs) replaced months of expert manual data mapping, dramatically accelerating data consolidation [07:18].
- Quote: “With the invention of generative AI and large language model, we were able to use large language models to help us to do the same mapping that rather would have required subject matter experts... and months of their time...” — Yogurt Jayapakasam [07:36]
- Three Lenses for AI Application:
- AI for technology (e.g., software development)
- AI for operations (e.g., closing finances, automating exceptions)
- AI for customers (e.g., personalized services, payments automation)
AI at the Core of Product Innovation
- Deluxe AI Platform ("DAX"): Internal AI platform with custom wrappers and business rules on public LLMs; platform is tailored per business unit for customer service and automation.
- Quote: “We have one chatbot, but it has the intelligence and awareness of every different business unit.” — Yogurt Jayapakasam [10:44]
- Generative AI in Receivables (R360 Plus): Used for automating cash application, invoice extraction, and streamlining payments—a process previously performed by analysts in hours/weeks now reduced to real time.
AI Architecture & Safeguards
- Hybrid AI Deployment: Combines public cloud LLMs with Deluxe’s own “trust layer” to ensure sensitive data remain protected. Utilizes Retrieval Augmented Generation (RAG) for secure, context-aware AI [12:14–12:54].
- Risk-Based Approach: Started AI use in low-risk, internal areas before expanding to customer-facing applications.
- Guardrails and Committees:
- “Compliance by Design” in every AI use case
- Executive-level AI committee monitoring use, safeguards, and legal/privacy obligations
- Regular reviews with a client advisory board, ensuring transparency and consent from top customers around data and AI use [13:49–15:50].
Talent, Upskilling & Organizational Design
- Diamond-Shaped Organizations: AI may shift company structures—fewer entry-level roles, broader mid-level, and small executive tiers. The focus must be on upskilling the existing workforce [16:21–17:10].
- Quote: “Entry level career folks are going to require more soft skills and business domain expertise as quickly as possible. But the mid career folks are going to require upskilling with the AI technology.” — Yogurt Jayapakasam [18:21]
- Collaborative Training: HR and tech work together to deliver upskilling programs that bridge technical as well as domain and soft skills across career stages.
- Critical Soft Skills Identified:
- Ability to ask and reframe questions
- Critical thinking and challenging assumptions
- Deeply “falling in love with the problem” rather than the solution [19:26–20:40]
Executive Training & AI in Leadership
- Three-by-Three Upskilling Matrix: Training programs aligned to three AI proficiency levels (beginner, intermediate, advanced) for entry, mid, and executive tiers.
- AI for Executive Strategy: Leaders should leverage AI not just for operations but to shape strategy—replacing lengthy, expensive consultant projects with rapid AI-generated research and insights.
- Memorable Moment: Jayapakasam describes using AI (like ChatGPT, Perplexity) to draft a strategic research paper for executives in under two hours—“None of us were able to poke holes with the report that AI produced” [22:55].
The Human Element & Change Management
- Balance Between Growth and People: The biggest leadership challenge is to drive business growth through technology while bringing people along for the journey—accountability, empathy, and responsible AI adoption [23:39].
- Quote: “How are we going to balance between driving business growth and bringing our people along in the journey? And that in my opinion is the biggest challenge.” — Yogurt Jayapakasam [23:47]
Notable Quotes & Memorable Moments (w/ Timestamps)
- “We want to pivot to becoming a payments and data company where technology becomes the product and services that we sell and not the physical paper checks that we used to produce.” — Yogurt Jayapakasam [01:33]
- “AI's revolution now is culmination of capitalizing all the technology transformation that already took place and now they are all converging with AI.” — Yogurt Jayapakasam [02:59]
- “Technology is the smart smaller part in my opinion. It is mostly people and culture.” — Yogurt Jayapakasam [04:19]
- “With the invention of generative AI and large language model, we were able to use large language models to help us to do the same mapping that rather would have required subject matter experts... and months of their time...” — Yogurt Jayapakasam [07:36]
- “We have one chatbot, but it has the intelligence and awareness of every different business unit.” — Yogurt Jayapakasam [10:44]
- “Entry level career folks are going to require more soft skills and business domain expertise as quickly as possible. But the mid career folks are going to require upskilling with the AI technology.” — Yogurt Jayapakasam [18:21]
- "How are we going to balance between driving business growth and bringing our people along in the journey? And that in my opinion is the biggest challenge.” — Yogurt Jayapakasam [23:47]
Key Segment Timestamps
- Transformation overview: [00:34]–[02:50]
- AI as force multiplier: [02:50]–[03:51]
- Digital-first culture: [03:51]–[05:58]
- Data strategy & AI: [05:58]–[09:40]
- AI for customer offerings: [09:58]–[12:03]
- AI architecture & security: [12:07]–[15:50]
- Upskilling & talent strategy: [16:02]–[21:21]
- Executive AI training: [21:21]–[23:39]
- Closing thoughts: [23:39]–[24:36]
Summary
This episode offers a comprehensive look at Deluxe’s multi-year transformation from a print-focused manufacturing firm into a tech-forward, AI-driven payments and data company. Yogurt Jayapakasam candidly shares how Deluxe built its strategy on people and culture, leveraged AI to accelerate innovation, and adopted rigorous governance for data and ethics. Key takeaways include the importance of soft skills in a digital era, structured upskilling across organizational layers, the fusion of HR and tech in change management, and using AI as a leapfrog—not just optimization—opportunity. This candid conversation is rich in practical insights for any executive leading or considering a major digital transformation.