From an early successful career in music to writing speeches for a US senator, David Oskandy’s broad experience and multiple skillsets prepared him well for the technological disruption that CDW helps its customers to navigate with full-stack technology prowess. His agility in leading people, solving problems, and building initiatives across wide-ranging disciplines launched an in-house legal career that spans an array of legal areas and industries at such high-profile players as Arthur Andersen, Honeywell, Wrigley, and Avanade—the joint venture of Microsoft and Accenture. At Avanade, he received the “Transatlantic General Counsel of the Year” award from the 2019 Transatlantic Legal Awards committee.
The current deputy general counsel for international, M&A, and strategic initiatives at CDW has served as an advisor to his executive coworkers, spotting future opportunities and building them into innovative, market-leading approaches. He leaned into robotic automation and AI in the legal sector years before the movement caught hold. Drawing on the shape of his own career trajectory, he stresses the need for lawyers to embrace change, and he spawns reinvention for continuous improvement using design-led thinking and the latest technology platforms to enable instant collaboration across a variety of dimensions.
Oskandy embodies his philosophy, stating, “Continuous growth is fundamental to a fulfilling career, and that mindset is very important to attracting, retaining, and growing the kind of dynamic talent that enables business growth.”
A Reputation for Innovation While Emphasizing Humanity
Driving tech innovation in the legal sphere while also prioritizing human communication are not inherently contradictory aspirations; however, it does take a special mindset, technical mastery, and a deep understanding of the human element to effectively navigate both simultaneously. Yet, amidst this intricate balance, he maneuvers through both realms with finesse and foresight, integrating cutting-edge technological solutions while fostering open dialogue and meaningful engagement. With this unique perspective, he’s been driving global M&A and creating revenue growth everywhere the attorney has landed.
At Avanade, Oskandy helped reposition the company by creating new capabilities and offerings, an evolution that increased revenue three-fold. He built the global M&A function at Arthur Andersen and would later help Wrigley reach its $5 billion growth objective.
Since assuming his present role in 2021, Oskandy harnesses the power of the legal team to build initiatives across departments, cultures, and geographies to develop new opportunities for CDW. He initiated a comprehensive transformation within the international legal team, reshaping its reporting line, vision, mission, principles, methodology, and matrix.
This strategic overhaul laid the groundwork for a cohesive and agile approach to navigating the complexities of international law with precision and effectiveness. Further, he spearheaded the implementation of AI technology and offshore resources for M&A due diligence, boosting deal efficiency and speed while empowering transformative M&A strategies. Moreover, he fostered a dynamic organizational culture characterized by a relentless pursuit of creativity, continuous learning, and problem-solving, instilling a sense of value and empowerment for pioneering approaches and inspiring the team to challenge itself to continuously evolve at pace with emerging technologies.
“David is the kind of legal executive that every business would love to have, with a keen focus on identifying, mitigating, and managing risks, while effectively driving incremental business value,” says Kristofer Swanson, vice president and forensic services practice leader at Charles River Associates. “He is particularly skilled at navigating the knotty jurisdictional and ethical issues associated with doing business internationally. And somehow, he also finds the time to give back concurrently to the community in meaningful and substantive ways.”
The Art of Being Future Ready
The key in driving technological innovation for decades, Oskandy explains, is redefining what it means to be a lawyer. “A successful twenty-first century lawyer must be forward-looking and agile, reshaping the legal function to be a value generator while working across borders in multicultural teams to enable business objectives. They excel at crafting innovative solutions, and value collaborative input to inform their decisions,” Oskandy says. “This is the kind of future-ready profile we must maintain if we want to continue to push the boundaries of what is possible.”
Oskandy brings his growth mindset to his work in the public sphere and in the corporate world, serving as a role model for future leaders. He serves on the Development Committee for JA Worldwide, whose aim is to build organizational, entrepreneurial, and financial literacy skills for youth. He also serves on Northwestern’s Alumni Admission Council; has served as a member of the board of trustees and a gala host committee member for the University of Chicago’s Court Theatre; and has been a guest lecturer for the University of Chicago’s Law School.
His work all comes back to the lawyer’s desire to continue growing. The musician, speech writer, and world-class global legal leader with one eye always on the future clearly values the opportunities he has had in complex international organizations that have led him to CDW. He splits time between Chicago and Mexico City with his bicultural, bilingual family and says that the exhilaration of leading people, solving problems, and building initiatives across geographic, cultural, and professional boundaries continues to inspire his legal career.
Sirisha Gummaregula, COO of QuisLex Inc, emphasizes how Oskandy’s pursuit for innovation inspires others. “David is a remarkable combination of razor-sharp intellect with great humility and compassion,” she says. “He’s superb lawyer with superior analytical skills who knows intuitively where his teams need to get to and helps them get there! He’s an inspiring leader with a strong understanding and love for technology, innovation, and change.”
If you walk away with one lesson from Oskandy, it could be to pursue M&A perfection or it could be the importance of learning the complexities of driving technological innovation from the legal chair with a global mindset. But more broadly, it’s that change can be an incredible experience as well as an opportunity for growth and transformation. Seek it out and embrace what comes next.
Expertise Spotlight
CRA’s Forensic Services Practice helps companies and their counsel independently respond to allegations of fraud, cybercrime, misconduct, and non-compliance, often in moments of crisis. These allegations span a broad range of matters, such as accounting irregularities, money laundering, cyber-crime, False Claims Act violations, ABAC/FCPA, #MeToo, healthcare fraud and abuse, Ponzi schemes, and trade secret thefts.
The practice is particularly sought out to assist with complex investigations, requiring deep industry knowledge and multiple technical competencies, and the experience to navigate thorny jurisdictional and ethical issues, comply with challenging reporting and disclosure obligations, and testify on both liability and damages. From a geographic perspective, its assignments have extended to Asia, Africa, Europe, Australia, the Middle East, North America, and South America.
The practice has been recognized by the National Law Journal for being one of the top three forensic accounting providers in America, and by Global Investigations Review as one of the leading investigative consultancies from around the world for handling sophisticated cross-border, government-driven, and internal investigations.
Operating from ten countries around the world, CRA’s clients over the past two years included 97 percent of the AmLaw 100 law firms and 81 percent of the Fortune 100 companies.
