Above The Treeline with Andy Young

Built for Distance: How USAA Engineered Digital Access Long Before “Digital Transformation” Became a Strategy

Episode 25 of Above the Treeline features Andy Keller, a 42-year veteran of USAA Insurance who began his career in 1984 as part of a government-sponsored IT co-op program and retired as a Technical Architect Lead. Over four decades, Keller worked across core claims systems, document composition, image capture, e-delivery, cloud migration, and enterprise modernization initiatives. With renewed conflict in the Middle East and American service members once again deployed into harm’s way, it feels appropriate to pause and acknowledge the families who carry that weight. USAA was built to serve them. As a non-veteran member of USAA, my connection is through family. My father served in the Marine Corps. My wife’s father served in the Army. Like many members, our relationship to USAA is generational. It is rooted not only in financial products, but in service. Because long before “digital transformation” became an industry strategy deck, USAA was solving a practical problem: how do you serve members who may be anywhere in the world, often far from home, often in unstable environments, and still ensure continuity of their financial lives? That question shaped architecture. It shaped communications. And, in this episode Andy Keller makes clear, it pushed USAA toward digital access decades before much of the broader customer communications industry began to move. From COBOL to Cloud Keller entered USAA at a time when customer communications were inseparable from mainframe logic. COBOL, PL/I, assembler, JCL. Xerox MetaCode driving print streams. AFP conversion. Automated document factories. Inserters. Postal optimization. Paper was not a channel choice. It was infrastructure. One of his early assignments involved what would later become a precursor to digital document rendering: capturing output, overlaying data, managing fonts via XY coordinates, and enabling internal service representatives to view member documents electronically. That work predated widespread internet adoption. The architectural seeds of digital were present long before the market language caught up. Digital as Operational Necessity USAA’s founding constraint serving military families who could be deployed anywhere in the world shaped its communications strategy long before “digital transformation” became an industry phrase. Keller was part of the team that helped implement USAA’s early electronic delivery capabilities. By the early 2000s, the organization was delivering policies and statements through web and mobile platforms. Adoption was slow and steady—approximately three percent per year over two decades, until digital became the behavioral norm. Today, digital adoption exceeds 70 percent. More importantly, the cultural posture has shifted. Paper is no longer presumed. It is optional. The Regulatory Gate Keller describes the most significant early barrier not as technical, but legal. Compliance teams interpreted statutory language such as “written notice” as inherently requiring physical mail. Only when regulatory clarity explicitly permitted electronic delivery did institutional momentum accelerate. This is a recurring pattern across regulated industries. Technology capability precedes regulatory comfort. The constraint is interpretation, not innovation. The Seven-Foot Stack One memory Keller shared is instructive: a member once stacked every piece of USAA mail received over time. The pile stood roughly seven and a half feet tall. That visual reframes the direct mail debate. From the sender’s perspective, each piece fulfilled an obligation or represented opportunity. From the recipient’s perspective, it accumulated as volume. As waste. As digital access matured, paper increasingly became triage sorted over a recycling bin, with only urgency determining survival. The authority of the printed artifact erodes when redundancy became visible. Charging for Paper USAA experimented for years with incentives to encourage electronic adoption. The inflection point came when paper statements carried a modest monthly fee and digital adoption jumped materially from 3–4% to 7% or more. The lesson is uncomfortable but clear: cost shifts behavior faster than encouragement. As institutions approach 80 percent digital participation, similar economic signals will likely become even more common. Obligation vs. Opportunity Keller frames the internal divide as obligation versus opportunity. Operational communications such policies, disclosures, statements are compliance bound. Marketing communications pursue growth and brand reinforcement. Historically, these streams operated in parallel stacks. Different systems. Different governance. Different incentives. The unresolved challenge is integration: how to fragment content dynamically for experience optimization while maintaining regulator-approved language structures that were designed for fixed layouts and immutable pagination. This becomes not a print-versus-digital debate, but an orchestration problem. The Postal Dimension Keller also served for decades in local public office, including as mayor of a small Texas municipality. That dual exposure of enterprise architecture and public governance shaped his view of institutional inertia. The Postal Service, constitutionally embedded, is not obsolete. But its operating assumptions were built for a correspondence era. Return mail volume such as checks mailed back to billers was the first major collapse. Electronic bill presentment and payment removed a foundational volume from the postal stream. The next shift is subtler: as transactional communications become digitally default, physical mail concentrates into parcels, logistics, and selective high-value touchpoints. AI: Accelerator, Not Apocalypse From Keller’s technical perspective, AI is less existential than evolutionary. Its most immediate value lies in interrogating legacy systems, extracting business rules embedded in decades-old code, and accelerating modernization cycles that historically stalled under technical debt. Insurance products often contain state-specific logic encoded in languages whose original authors have long retired. AI’s opportunity is institutional memory recovery. The risk is governance complacency. Garbage in, garbage out still applies. AI does not absolve accountability. The Default Is Moving Andy Keller’s career arc from mainframe-based document factories to cloud-based digital orchestration mirrors the broader shift underway across regulated industries. Paper began as infrastructure.Digital began as an accommodation.Digital is now becoming the default. The decisive transition is not channel substitution. It is authority migration. It is gravity pulling the center of customer communications to a new place. When the mobile interface becomes the starting point of the customer relationship, gravity shifts upstream into data, orchestration logic, compliance architecture, and AI-assisted intelligence layers. USAA was built to serve members at a distance.A century later, that distance remains, and connecting matters more than ever. Notice Special thanks to Andy for his time and insights. It should be stated that Andy’s opinion’s are his own and do not reflect the position or views of USAA Insurance. Get full access to TreelinePress at treelinepress.substack.com/subscribe [https://treelinepress.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Accessibility as a Service Isn’t Just for People. It’s for Agents, Too!

When I sat down with Ernie Crawford, President and CEO of Crawford Technologies, I wasn’t expecting such a personal story to launch our discussion on digital accessibility. But it was his mother’s declining vision and a stack of unreadable investment statements that ultimately helped shape a technology platform now used by some of the world’s largest banks, healthcare companies, and service providers. In this first in-person, audio podcast episode 22 of Above the Treeline, Ernie and I unpack what “Accessibility as a Service” really means today. It’s no longer just about meeting ADA or WCAG requirements. It’s about automation, real-time delivery, customer experience, and increasingly, machine readability in an AI-driven world. Crawford Technologies deserves real credit for helping lead the accessibility conversation across the CCM industry. Long before it became a regulatory flashpoint or an RFP requirement, Ernie and his team were building the tools, platforms, and education that helped make digital accessibility a strategic priority. Now celebrating its 30th anniversary [https://crawfordtech.com/press-release/30-years-of-innovation-growth-and-customer-centric-excellence/?utm_content=366931300&utm_medium=social&utm_source=linkedin&hss_channel=lcp-679786], CrawfordTech has established itself as a trusted partner to over 2,000 organizations on six continents, consistently earning top marks for innovation, service, and customer satisfaction That longevity is paying off: the company reported record revenues in 2025 [https://crawfordtech.com/press-release/record-revenues-and-strategic-growth-in-2025/], with a 41% year-over-year increase in accessibility services and 47% growth in European markets. A significant share of that momentum is being driven by expanding adoption of AccessibilityNow Translate and increased demand for scalable, cloud-based SaaS delivery models More than a technology story, it’s also a story of sustained leadership. CrawfordTech marked its anniversary with a reaffirmed commitment to solving complex customer communication challenges delivering innovation with a human touch. Key Takeaways Accessibility goes beyond complianceAccessibility is no longer just a legal checkbox. It improves SEO, supports machine agents, and strengthens CX. As Ernie put it, “The approach we take is to make it both accessible and usable” Large print is not just a font changeIt’s full recomposition. Following Clear Print standards, Crawford reduces the bloat while maintaining readability typically 2.5x expansion in the number of printed pages instead of 9x. The next frontier: multilanguage PDFsOne PDF, multiple layers, multiple languages selectable by screen reader or viewer. Crawford is working with industry experts like Duff Johnson and PDF Association to make this both usable and testable across platforms. TreelinePress is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Accessibility isn’t just for the disabled, it’s for the agents, too. In a future where machines read and act on our content, proper tagging and structure will define how organizations deliver value, stay compliant, and compete. If you’re a service provider and not already offering accessibility, it might be time to start. This is just a slice of what Ernie and I covered—from the flaws in composition engines to the realities of batch versus real-time remediation. It’s a must-listen for anyone in the customer communications, print service, or compliance tech space. Sneak Peak: Industry Summit, April 8–9 in Orlando Crawford Technologies and Madison Advisors [https://crawfordtech.com/industry-summit-2026/] are teaming up for an expanded edition of last year’s successful industry roundtable. Expect deep dives on regulatory shifts, document tech strategy, and AI’s growing role in content accessibility. Hear why he believe it is this years must-attend CCM event. Final Thoughts The world of customer communications is evolving—and accessibility is no longer optional. As Ernie shared, whether it’s responding to regulatory pressure, delivering a better customer experience, or enabling AI-driven document intelligence, accessibility is now table stakes. Service providers and enterprise tech teams have a real opportunity here—not just to comply, but to compete. Interested in having your company featured on Above the Treeline? We’re always looking for sharp perspectives and innovative voices shaping the global future of customer experience, communications, compliance, and AI-related technology. If you’ve got a story worth telling, let’s talk. Reach out to info@treelinepress.com, connect with me directly on LinkedIn. Get full access to TreelinePress at treelinepress.substack.com/subscribe [https://treelinepress.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Rethinking the Document of Record: Is PDF the Only Option?

I recently had a great conversation with Duff Johnson from the PDF Association. Duff has spent his career advocating for PDF, and for good reason. PDF has been one of the most important and enduring standards in enterprise communications. I’ve personally spent more than 30 years working with PDF and Adobe Acrobat, going back to the early days when simply being able to preserve layout digitally was transformational. So this conversation with Alan Berger is not about whether PDF is good or bad. It’s about asking a different question. Is the document of record inseparable from the page, or are there now compliant alternatives that better align with how customers and systems interact today? ==================================== For decades, regulated customer communications have followed a familiar pattern. A document is created, delivered and archived.A checkmark for compliance. That model made sense in a paper-first world where proof of delivery was the primary objective. Proof that something was sent. Proof that it was printed. Proof that it could be retrieved years later if needed. But the world around those communications is changing. In my recent Above the Treeline podcast conversation with Alan Berger, CEO of InfoSlips North America, we kept returning to the same realization. The industry is not being held back by technology. It is being held back by a mindset that still treats communications as the end of the process rather than part of an ongoing relationship. A conversation. This is not a debate about whether PDFs are good or bad. PDFs remain an important and reliable workhorse across regulated industries. The issue is more subtle and more consequential. The problem emerges when page-based, document-centric thinking becomes the ceiling for digital progress. When the page became the experience Most regulated communications today are still shaped by their print origins. The same file that once drove a printer is now delivered through a portal or an email notification. From an operational perspective, very little has changed. Only the transport mechanism is different. From a compliance standpoint, the requirement may be satisfied, but from a customer standpoint, the experience often feels disconnected from everything else. Customers engage with organizations through mobile apps, websites, alerts, and messaging channels that are responsive and contextual. When a statement, policy notice, or regulatory disclosure arrives as a static artifact, the contrast is immediate. In my conversation with Alan, he described how regulated communications are often viewed as a sunk cost. Something the business has to do, not something it can learn from, improve, or design around customer understanding. As a result, these communications frequently sit outside digital transformation programs, outside customer experience strategies, and outside AI roadmaps. What regulation actually requires One of the most persistent myths in this industry is that regulation mandates a specific format. In reality, most regulations focus on outcomes, not file types. They emphasize immutability, audit readiness, authentication, retention, and accessibility. They do not require information to be delivered as a page-based document, just that they are “written communications” or “in writing.” This distinction matters. From a UK perspective, the direction of travel is becoming clearer through the FCA’s Consumer Duty framework and the more recent PS25/13 policy statement. [https://open.substack.com/pub/treelinepress/p/from-fireandforget-to-proofandperformance?r=58dlew&utm_campaign=post&utm_medium=web] Together, they indicate a shift away from fire-and-forget communications toward proof and performance. The regulator is no longer focused solely on whether information was sent. Increasingly, firms are expected to demonstrate that communications support customer understanding and appropriate outcomes. Electronic delivery becomes the default not because digital is convenient, but because digital enables evidence. Evidence enables testing. Testing enables improvement. Digital delivery is not digital experience Many organizations believe they have modernized because they reduced print volumes or moved customers to online portals. But placing a PDF behind a login screen does not create a digital experience. It simply relocates a legacy artifact. For customers, especially on mobile devices, long documents can feel more like images than information. They are difficult to navigate, difficult to interpret, and disconnected from the moment the customer is trying to resolve. Most communications were built to optimize production and distribution, not comprehension and interaction. TreelinePress is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. Strategic distance and why leaders are pulling ahead This issue becomes even clearer when viewed alongside broader global banking transformation. In its research on how retail banks build strategic distance, McKinsey & Co [https://www.mckinsey.com/industries/financial-services/our-insights/how-retail-banks-build-strategic-distance?] describes how leading institutions are separating themselves from competitors through digital capabilities that reshape customer experience, not just operational efficiency. The consistent message is that differentiation no longer comes from products alone. It comes from how effectively organizations design and connect customer journeys. Digital leaders do not modernize one part of the experience while leaving others frozen in time. Rethinking the document of record The document of record still matters. Immutability still matters. Auditability still matters. What changes is how the customer interacts with that information. Instead of freezing experience at the moment of composition, communications can be structured in ways that allow them to adapt across devices, support accessibility by default, and present information in context. The record remains intact, but the experience becomes dynamic. This distinction becomes even more important as AI and agent-driven experiences begin to shape how people interact with information. Agents do not read pages. They work with structure, context, and meaning. From documents to understanding At its core, this is not a file format discussion. It is a purpose discussion. Is the goal simply to deliver information, or is it to ensure understanding? When communications are designed around understanding, they can reduce confusion, lower call center demand, improve satisfaction, and strengthen trust. When they are designed solely around output, they quietly introduce friction at exactly the wrong moment. The traditional model of produce, send, archive is not wrong. It is just no longer enough. Andy’s Thoughts The future of regulated communications will not be defined by whether something is paper or digital, PDF or not PDF. It will be defined by whether the communication helps someone understand what matters to them at the moment they need it. Compliance will always matter. Records will always matter. But selecting a channel and checking a box is no longer the finish line. The organizations that pull ahead will be the ones willing to look beyond the page. That shift is already underway. Get full access to TreelinePress at treelinepress.substack.com/subscribe [https://treelinepress.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Ahead of Its Time: A Conversation with Annemarie Pucher

One of the more fascinating conversations I’ve had in a long time didn’t start with AI, agents, or customer experience buzzwords. It started with a LinkedIn post about preserving intellectual knowledge. That article, “The Vanishing Wisdom: The Knowledge Tapped Between Two Ears,” [https://www.linkedin.com/pulse/vanishing-wisdom-knowledge-tapped-between-two-ears-annemarie-pucher-fvoze/?trackingId=%2BW2qEtcrTpKejZfykJ9IWQ%3D%3D] https://www.linkedin.com/pulse/vanishing-wisdom-knowledge-tapped-between-two-ears-annemarie-pucher-fvoze/?trackingId=%2BW2qEtcrTpKejZfykJ9IWQ%3D%3Dwas written by Annemarie Pucher, CEO of ISIS Papyrus Group, and it immediately got my attention. Not because it was provocative, but because it articulated something I’ve watched enterprises struggle with for years, and have experienced firsthand when experts with decades of knowledge and judgment retire or walk out the door. What followed was a wide-ranging conversation that made one thing very clear. Papyrus Software hasn’t been chasing where the CCM market says it’s going. They’ve been quietly building for where enterprises eventually have to go. Before “Agents” Had a Name Papyrus came out of the same origins as many long-standing CCM vendors in the late 1980s: mainframes, printers, Xerox 9700s, and direct-to-output architectures. But instead of staying anchored to output, they moved early into something most of the market resisted at the time: process. A document without a process, as Annemarie put it bluntly, is worth nothing. By the early 2000s, Papyrus was already closing the loop between inbound and outbound communications, integrating data capture, classification, and automation while most organizations insisted those worlds should stay separate. Then came a detail that feels almost surreal in hindsight. In 2008, Papyrus patented what they called a user-trained agent. At the time, nobody really knew what to do with agents. The industry didn’t have language for it. There was no category to put it in. Today, everyone is talking about agents. The Enterprise as a Living System I really love the way Annemarie describes the enterprise. Not as a stack or a collection of tools, but as a living system. More like a doctor diagnosing a patient than an architect assembling components. Documents, data, and processes aren’t separate domains in this view. They are indicators. Evidence of decisions. Traces of how work actually gets done, including all the exceptions, workarounds, and human judgment that never make it into formal documentation. TreelinePress is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber. This perspective matters because it reframes the problem enterprises are trying to solve today as they rush to feed LLMs and AI systems. The issue isn’t just automation. It’s visibility. It’s understanding why decisions are made, not just what happened. That’s also where knowledge loss becomes painfully real. When experienced people leave, the rules don’t just disappear from systems. They disappear from context. From memory. From the space between two ears. Why This Matters Right Now It’s impossible to have this conversation in 2026 without talking about AI. But what made this discussion different with Annemarie was how grounded it was. AI doesn’t fail because models aren’t powerful enough. It fails because enterprises lack context. Without shared language, visible rules, and clear process intent, intelligence becomes guesswork. Papyrus’ focus on adaptive processes, business language, and ontology isn’t academic. It’s foundational. AI needs something to reason over. It needs enterprises that can describe themselves clearly and consistently. In that sense, Papyrus wasn’t early to AI. They were early to what AI actually needs in order to work effectively. Andy’s Take You often hear about AI as if it is something you can bolt on at the end of an outdated process. A magic bullet that will make all things possible. This conversation made the opposite case. Intelligence starts with understanding how work actually gets done. It starts with capturing judgment, exceptions, and intent while that knowledge still exists. AI doesn’t replace that work. It depends on it. Too many transformation efforts fail because enterprises try to automate what they don’t truly understand. They digitize outputs without addressing the processes and decisions underneath. Then they wonder why AI projects struggle to deliver meaningful results. Papyrus’ story is a reminder that real progress often looks boring before it looks brilliant. It doesn’t announce itself with buzzwords. It shows up quietly, years ahead of demand, waiting for the rest of the market to catch up. Get full access to TreelinePress at treelinepress.substack.com/subscribe [https://treelinepress.substack.com/subscribe?utm_medium=podcast&utm_campaign=CTA_4]

Stop Dragging Prints Past Into the Future

There’s something appropriate about opening 2026 with a conversation recorded at the very end of 2025. One year closing, another opening and where you stop debating tactics and start asking more fundamental questions. Not what should we improve, but what are we actually holding onto that no longer works. That was very much the spirit of this conversation with Ray Stasieczko, host of End of the Day with Ray [https://www.youtube.com/results?search_query=end+of+the+day+with+ray] on YouTube. I originally reached out to Ray with a fairly specific question: Why should print service providers be paying attention to what’s happening with the big OEMs? That question lasted about five minutes. From there, the discussion expanded quickly into end-user behavior, declining print volumes, AI hype versus data reality, parcels versus mailboxes, and why 2026 may be the year the industry finally runs out of room to postpone hard decisions. What surprised me most wasn’t disagreement. It was how often Ray and I, despite coming from different vantage points, landed in the same place. Different Lenses, the Same Conclusion Ray and I don’t approach the industry the same way. He tracks the business of print: OEM strategy, dealer economics, capital structures, and where hardware-centric models start to strain. I focus on print volumes and the broader migration of customer communications away from paper and into digital, interactive environments. Yet despite those differences, we kept circling back to a shared realization: The industry doesn’t have a value problem. It has a volume problem. That distinction matters more than most people want to admit. Value arguments are emotional. Volume is structural. Volume determines: * Whether presses stay busy * Whether service contracts make sense * Whether consumables scale * Whether labor models hold * Whether capital investments can be justified “The industry keeps talking about how valuable print is. The ecosystem doesn’t run on value, it runs on volume.” As volume declines, even gradually, the entire economic model starts to destabilize. And no amount of optimism changes that math. The End User Isn’t in the Mailbox Anymore One of the most revealing moments in the conversation came when we stopped talking about equipment entirely and started talking about behavior. Ray asked a question that felt almost too simple: “Who the hell wants to go to their mailbox?” That question cuts through a lot of industry noise. People don’t avoid information.They avoid friction. The modern end user expects communications to show up: * Where they already are * When it’s relevant * In a format that’s easy to act on That reality is why parcels and packages came up so quickly in the conversation, not as logistics, but as attention moments. A package gets opened immediately. Mail gets sorted, stacked, ignored or thrown in the bin. From there, the discussion moved naturally away from printed inserts and toward something much more telling: “It’s not even going to be a printed material in the box. It’s going to be a QR code in the box.” That single shift reframes how we should think about direct mail, advertising, and transactional communications. The opportunity isn’t about printing better. It’s about meeting the customer at the moment they’re already engaged. Stop Dragging the Past Into the Future A recurring frustration throughout the conversation was how much energy the industry spends trying to preserve familiar models instead of designing new ones. Ray was direct about it: “Everybody’s trying to drag outdated processes into the future instead of figuring out how to disrupt themselves.” That mindset shows up everywhere: * Digitizing legacy workflows instead of replacing them * Using AI to automate bad processes * Treating incremental change as transformation The industry has become very good at selling reassurance to itself. But reassurance doesn’t change customer behavior. And it doesn’t reverse declining volumes. AI Isn’t the Strategy, Data Is No year-end conversation would be complete without AI coming up, but this one avoided the usual hype entirely. Ray’s position was clear: AI is not the problem, and it’s not the solution either. “AI is just going to take your data and digest it. If your data’s screwed up, AI is irrelevant.” The real issue isn’t intelligence, it’s discipline. AI doesn’t fix broken data.It exposes it.It accelerates whatever foundation already exists. For companies hoping AI will magically rescue outdated systems or unclear strategies, that’s a dangerous assumption. Why 2026 Is Different When I asked Ray what he sees coming next, his answer wasn’t about features or formats. It was about financial pressure. “We’re going to see the money look at this industry in a whole different way.” In Ray’s view, 2026 is when patience runs out. That means: * OEM shakeups become unavoidable * Some industrial print players exit altogether * Capital markets stop accepting “long-term transition” narratives * Boards and private equity demand clarity, not comfort Incrementalism won’t survive that scrutiny. “You can’t be dragging the past into the future.” A Personal Note Before closing, I want to acknowledge that Ray is one of those who encouraged me to just do it, and start a podcast. Not to wait until it was perfect. (Which is video is not!)Not to over-engineer it.Just to start having the conversations. (The best part!) That advice stuck. These podcasts may not be polished or beautiful, but they contain something far more important: real experience, honest perspective, and conversations the industry often avoids. For that encouragement, and for consistently saying the quiet part out loud, I’m grateful and look forward to many future conversations with Ray. Final Thought This conversation with Ray wasn’t about being negative on print. It was about being honest about where communications are going and whether the industry is willing to follow them. Communications are not disappearing. They’re relocating. Finding a new home in a digital eco-system. 2026 will reward the companies that understand that difference and challenge those that keep defending the output instead of the outcome. Listen to the full podcast to hear where Ray and I align and what he believes is coming next for OEMs in 2026. 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