Law with Backbone: Björn Holeschak’s Stand for Digital Dignity

The Most Influential People in Legal Services to Watch in 2025

Some people are simply wired differently, driven by a deeper purpose that shapes their entire journey. Björn Holeschak, Head of Legal & Compliance at Eye-Able®, is one such individual whose path to leadership in legal and compliance began long before entering the corporate world. He forged his foundational grit as a soldier and IT operator, mastering high-pressure IT security with an unwavering “mission first” attitude. This discipline was profoundly balanced by a childhood rooted in integrity and a warm, humanistic worldview. That clear moral compass stayed with him, guiding his transition to civilian life and into law, where he sought to bridge legal obligations with technological realities. This quest led him to his calling: accessibility, a domain where his tech smarts, legal expertise, and heartfelt belief in equal opportunity perfectly converge. For Björn, digital access is a fundamental human right, and making it a reality is the powerful force driving him today. Learn more about Eye-Able®’s vision for digital inclusion and how it shapes their mission.

Promoting Inclusion Through Legal Fortification

This seasoned executive believes digital inclusion is far more than a moral imperative. It’s one of the biggest untapped business opportunities around. With exciting tech like augmented reality and virtual intelligence, we now have the power to craft digital spaces that truly empower everyone, regardless of their abilities, to thrive on their own terms. This deeply aligns with Eye-Able®’s core mission, and Björn’s legal approach reinforces it at every step. “I see my role as a connector,” he explains, “Translating legal frameworks and compliance requirements into secure, scalable solutions that clients and society can trust.” By ensuring a crystal-clear legal footing from day one, they smooth out problems, minimize risks, and accelerate the adoption of vital accessibility tools. Crucially, they open countless doors to learning, groundbreaking ideas, and global engagement. Each obstacle they remove unlocks vast human potential, economically, socially, and intellectually. To Björn, contributing structure, direct communication, and sharp legal expertise means he’s truly making an impact.

The Global Accessibility Maze

When asked about the unique hurdles he faces in ensuring accessibility software meets global standards, Björn immediately points to the complex web of international regulations. Digital accessibility is a growing global need, but the rules vary significantly, considering the EU’s Accessibility Act versus the ADA in the U.S., as well as unique standards in the UK, Italy, and the Netherlands. Making sure everything fits across these locations needs a super adaptable compliance plan.

Additionally, there’s the fact that “accessibility” itself isn’t always clearly defined in the law. Many rules talk about “reasonable accommodations” or “equal access” without saying exactly what that means in actual code. This legal uncertainties require thoughtful interpretation – and present a chance for responsible leadership.

Data protection is another big hindrance, especially when accessibility tools handle user info or link up with assistive tech. They’ve got to meet GDPR, CCPA, and other privacy laws, all while keeping things easy to use.

Finally, how people see accessibility changes from one market to another; in some places, it’s just a box to tick. In others, it’s a must-have strategy. Björn’s job is to support both perspectives: enabling enterprise trust while promoting systemic digital equity.

The Innovation-Regulation Sweet Spot

Balancing innovation with regulatory obligations in a rapidly evolving legal-tech environment is seldom as clean-cut as it sounds. Yet, Björn doesn’t see innovation and regulation as opposites. To him, they are co-dependent. He’s convinced that well-structured compliance can ignite creativity. The secret is embedding legal thinking early in the product development process, rather than tacking it on at the end.

At Eye-Able®, where legal tech meets accessibility solutions, Björn’s essential role is to guarantee that the company’s expansion remains legally sound. This means crafting supportive frameworks, not roadblocks.

He works closely with product and engineering teams, distilling complex legal mandates into clear parameters, identifying what is required, what is optional, and where we can safely push boundaries.

Anticipating changes is equally important. Hence, Björn actively monitors new laws, policy changes, and emerging standards across the spectrum from cutting-edge AI to crucial ESG principles. The objective is more than just following the rules. It is about predicting what’s next and adjusting their strategy proactively. This enables faster progress, smarter offerings, and a distinct advantage for Eye-Able®’s clients. As Björn states, “Real innovation isn’t just about what you build; it’s about what you anticipate, enable, and make trustworthy over time.”

Personal Values That Guide in Complexity

When the path gets murky, a leader’s personal values quietly light the way through complex legal and ethical dilemmas. They infuse decisions, which often carry immense weight, with integrity and a human touch. What about Björn? Does he have any such code that he won’t compromise on? Yes, his line in the sand is clear. He affirms that integrity isn’t merely a rule he adheres to; it’s fundamentally who he is. He adds, “I was raised with a family motto: ‘Vivere – pugnare – caritate’ – Live, fight, help.”

These three words remain Björn’s constant guide to living with dignity, recognizing everyone’s inherent worth. To fight for one’s values, because principles only matter when tested. To help others, because the true measure of leadership lies in service.

This fundamental ethos is deeply intertwined with Björn’s role. The opening line of the German constitution states unequivocally: “Die Würde des Menschen ist unantastbar. – Human dignity is inviolable.” This isn’t just a law, but a sacred commitment that encompasses everyone. As a legal and compliance leader, he feels a profound obligation to embody that ideal in every decision, particularly when legal nuances are ambiguous or business demands are intense.

Björn approaches complex scenarios guided by three core values. First is clarity, because decisions demand a clear direction. Second is courage, as doing what’s right often requires a solitary stand. Third is compassion, because legal systems are crafted for people, not the other way around. He considers, “When we defend dignity, we strengthen society. And we grow ourselves.”

The Moment He Chose His Style

Two hard-hitting lessons set the tone for Björn’s leadership journey. First, in the military, he witnessed his Sergeant Major shielding his team from reprimand. To the Captain, he said, “If you have an issue with my team, take it up with me.” Instead of shifting the blame, the Sergeant Major took responsibility for a late arrival. That show of backbone taught Björn what authentic leadership looks like: accountability, taking the hit, protecting your people, and owning the outcome. Years later, sitting across the table from global legal teams who didn’t understand the tech, Björn found his purpose again. His frustration as a Data Protection Officer, repeatedly explaining technical concepts to lawyers, solidified his resolve to be a competent and clear communicator who bridges law and technology, earning respect through substance, not showmanship.

These moments taught Björn that legal leadership is about standing up for people, for clarity, and for a commitment to do better together.

The Art of Seamless Integration of Legal, Tech, and Executive Team

At Eye-Able®, Björn’s secret to fostering deep collaboration among legal, technical, and executive teams is simple. It lies in bridging gaps before they become bottlenecks. He acts as a “translator,” fluent in their different “languages.” He brings everyone together by focusing on a common goal of building products that are accessible, secure, and ready to grow. Grounded by his three core values of clarity, courage, and compassion, he turns legal input into action, gives teams the confidence to innovate, and creates space for joint problem-solving by listening and understanding. Drawing on his dual expertise in IT and law, he rejects silos and ensures legal is embedded early, not tacked on later. Björn feels that’s how collaboration becomes a part of company culture.

Most Proud Achievement in Legal Career

His greatest accomplishment in his legal career is the rock-solid legal and compliance framework he helped create at Eye-Able® for digital accessibility. The veteran is quick to say this structural base does much more than fulfill formalities. It’s about making accessibility a core part of every company function, from how products are designed to how customers are served and how the business is run internally. This includes progressive preparation for regulations like the European Accessibility Act and Germany’s BFSG. What truly fills Björn with pride, however, are Eye-Able®’s values. The fact that over 20% of their employees live with disabilities indicates that equity is more than just a talking point at Eye-Able®. “We don’t theorize inclusion,” Björn remarks, “We live it.” That authenticity sets the company apart. Clients don’t just get accessible solutions, but they gain a partner grounded in real-world experience. For Björn, that’s the legacy he wants to build: inclusion that scales because it’s built on truth, not tokenism.

Staying Ahead of the Curve

“In accessibility, waiting isn’t an option,” Björn demonstrates, “Leading is part of the job.”

Staying ahead in accessibility and data protection involves more than just monitoring. It necessitates actively influencing future regulations. At Eye-Able®, they closely track new legislation, such as the European Accessibility Act. They also identify regulatory gaps, evaluate current frameworks, and contribute to standardization efforts, including collaboration with organizations such as the Deutsches Blindeninstitutstiftung.

Internally, a “legal finding” initiative ensures every team member contributes to ongoing discussions, assessments, and strategic actions across product development, risk management, and policy, ensuring their compliance approach remains proactive.

Advice to Legal Professionals Moving into Tech and Compliance

Björn urges legal professionals eyeing tech and compliance roles to step out of their comfort zone. Rather than fearing technology, they must grasp the fundamentals and speak the language of those who build. Over time, Björn has come to realize that structure isn’t red tape. It is what gives innovation room to move. Therefore, he advises aspirants to make their guidance precise. He points out, “Compliance is about designing how to say ‘yes.'”

This industry leader endorses a mindset built on curiosity. In a space where laws shift rapidly, success depends on staying informed, testing assumptions, and challenging edge cases. But technical fluency alone isn’t enough. Real compliance work calls for grit. Therefore, he advises aspiring professionals to take responsibility, stand firm when it counts, and never be afraid to roll up their sleeves.

At Eye-Able®, this mindset is embedded in their institutional reflexes, from monthly legal reviews to day-to-day decisions. It helps them to stay sharp. When the pressure’s on, the legal team doesn’t retreat behind jargon. They lead with integrity, unshakable valor that doesn’t shout, and a kind of solicitude that never feels performative. These things keep them grounded.

The Evolving Role of Legal in Purpose-Driven Companies

Björn notices legal teams in purpose-driven companies evolving from risk-averse gatekeepers into forward-thinking enablers. He feels that the legal system must move beyond traditional approaches. Instead of reacting to problems, it must now help translate values into policy, ambition into process, and ethical goals into operating standards. At Eye-Able®, this means working side by side with product teams, aligning ESG goals with real-world compliance, and shaping standards in emerging areas such as accessibility and AI. To Björn, “Legal isn’t at the end of the process. It’s lighting the way forward.”

The Service of Shaping Mindsets

This seasoned executive measures his legacy by service (caritate in Latin) pulsating at its core. He aspires to leave an impact that goes beyond counting cold contracts or rigid policies. His true victory lies in a seismic shift in perception, where ‘legal’ is no longer a wall but a diligent force for trust and radical inclusion.

Much of his philosophy comes from outside the legal realm, particularly the world of endurance sports. Björn has competed in marathons, ultramarathons, and 24-hour races across Europe, experiences that have instilled discipline, patience, and resilience. “You learn to endure, to embrace discomfort, and to keep moving when it would be easier to stop.” That ideology shapes how he leads.

At Eye-Able®, he is not just focused on building strong legal frameworks. Björn is equally invested in cultivating a mindset within his team grounded in trust, responsibility, and quiet leadership. If that culture takes root and blossoms beyond him, he considers himself to have done his part.

He knows the day will come when he must step aside. “But when that day comes,” Björn reflects, “I want to know I’ve passed the baton to people who are better prepared and more grounded than I was when I started.” Like any well-run relay, the goal is not to finish alone, but to ensure the next stretch begins on stronger footing. That to him is the legacy: “to prepare, and to leave something better behind than what we found.”

The Pillars of Influence in Modern Legal Service

For Björn, actual influence in today’s tangled legal service has little to do with status or visibility. Nor does it reside in lofty titles or being the loudest voice in the room. Then what holds weight?

It’s a truth etched in sweat and grit that some of his sharpest lessons on influence were developed on the grueling tracks of European endurance races. These epic challenges helped shape his inner core. “True strength means staying the course,” he asserts, “pushing forward with discipline and focus, even when no one is watching.” That understated tenacity dictates how he operates with resolute integrity, day in and day out, in moments that rarely grab public gaze but build an unbreakable foundation of credibility.

For Björn, leadership is about empowering others to do the right thing, not through coercion, but through a powerful example. He builds legal structures that withstand immense pressure and equips others to do the same. He views his influence not as an endpoint, but as preparation for the next generation of legal professionals ready to pick up where he leaves off.