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Chicago - Managing Director, Endpoint Technology and Workplace Experience

Winston & Strawn LLP
United States, Illinois, Chicago
35 West Wacker Drive (Show on map)
Dec 24, 2025

ABOUT US

For Business Professionals, Winston & Strawn presents an exciting opportunity to be a part of a leading global law firm. With our commitment to excellence, diversity, a collaborative work environment, and an emphasis on professional growth, Winston offers a platform for individuals seeking to advance their careers in a dynamic and rewarding environment. Winston is known for its collaborative and collegial culture. We believe teamwork is an essential component in providing high-quality legal services and we value the talents and skills of our entire business professional team.

POSITION SUMMARY:

The Managing Director, Endpoint Technology and Workplace Experience is a strategic leadership role responsible for shaping and delivering a modern, secure, and seamless digital workplace experience for the firm. This role oversees endpoint strategy, device lifecycle management, collaboration tools, and workplace experience initiatives to ensure productivity, security, and satisfaction across the enterprise. The ideal candidate combines technical expertise with a strong focus on employee experience and operational excellence. The Managing Director, Endpoint Technology and Workplace Experience will lead a team of engineers and technicians, manage vendor relationships, and drive innovation to support a modern, hybrid work environment.

The Managing Director, Endpoint Technology and Workplace Experience will report directly to the Chief Information Officer (CIO) and will work closely with firm executive leadership, IS and administrative leadership, and practice group leadership to identify opportunities, develop and implement strategic initiatives, and ensure the effective provisioning of and access to innovative technology solutions across the firm.

DUTIES AND RESPONSIBILITIES:

Endpoint Technology

  • Lead a team responsible for driving the successful implementation and integration of endpoint technologies within the firm.
  • Define and execute the global endpoint computing strategy, including device management, operating systems, and application delivery.
  • Engage with attorneys and business professionals to assess their workflows, challenges, and technology needs.
  • Provide support for existing and new endpoint technology platforms, including laptop/desktop design, build and rollouts, as well as remote access platforms, establishing industry standard best practices and support level agreements.
  • Provide structured support, coaching, and change management strategies to ensure high user engagement and effectiveness.
  • Work with IT and business units to maintain a roadmap for currency and innovative edge in use of new endpoint platforms and methodologies.

Workplace Experience

  • Develop and execute a strategic vision for the firm's digital workplace experience, ensuring alignment with overall firm goals.
  • Drive initiatives to enhance the digital workplace experience, aligning with business objectives and employee needs.
  • Partner with IS, administrative and firm leadership to identify opportunities for the workplace experience to improve client service, operational efficiency, and practice group workflows.
  • Serve as an executive thought leader in workplace experience, representing the firm in industry discussions and client engagements on the future of legal technology.
  • Foster a culture of innovation, collaboration, and continuous improvement across all digital experience teams.

Team Management and Development

  • Provide strategic direction, mentorship, and performance management to the Endpoint Technology and Workplace Experience teams.
  • Build and maintain high-performing teams, ensuring appropriate staffing, training, and professional development.
  • Promote collaboration and knowledge sharing across teams and with other departments.

Stakeholder Engagement

  • Serve as a trusted advisor to firm executive leadership, administrative leadership, and practice group leadership on legal endpoint technology and workplace experience matters.
  • Collaborate with attorneys and business professionals to understand their needs and challenges and identify solutions that address their requirements.
  • Build and maintain strong relationships with external vendors and technology partners.
  • Present to executive leadership and practice leadership on legal technology roadmaps, progress, and financial implications.

Financial and Resource Management

  • Develop and manage the budget for Endpoint Technology and Workplace Experience, ensuring efficient allocation of resources.
  • Evaluate the ROI of technology investments and make recommendations for future initiatives.
  • Negotiate contracts with vendors and manage vendor relationships.

Risk Management and Compliance

  • Ensure that all technology initiatives comply with relevant legal and regulatory requirements, including data privacy and security.
  • Identify and mitigate technology-related risks.
  • Maintain awareness of ethical considerations relating to the use of AI and other emerging technologies in the legal field.

BASIC QUALIFICATIONS:

  • Bachelor's degree in business, computer science, communications, legal studies, or a related field required; an advanced degree (J.D., MBA, or MS in Data Science/Technology) preferred.
  • 10+ years of experience in a leadership role within legal technology, digital transformation, or data science required, preferably within a law firm or professional services environment.
  • Must live within a commutable distance to the firm office with the ability to come into the office 3-4 days per week.

ADDITIONAL QUALIFICATIONS:

  • Proven experience leading large-scale technology implementation and support initiatives.
  • Proven track record of successfully leading technology initiatives and driving innovation.
  • Strong understanding of legal technology trends and best practices.
  • Excellent communication, presentation, and interpersonal skills.
  • Ability to build and maintain strong relationships with stakeholders at all levels.
  • Strong analytical and problem-solving skills.
  • Experience managing budgets and vendor relationships.
  • Experience leading change management initiatives.
  • Demonstrated knowledge of security best practices.

COMPETENCIES:

  • Strong knowledge of legal technology solutions, AI applications in law, data management and strategy, and application development.
  • Exceptional leadership, team management, and interpersonal skills.
  • Deep understanding of law firm operations, legal practice workflows, and client service needs.
  • Ability to translate business objectives into actionable technology and change management strategies.
  • Strong stakeholder management skills, with the ability to engage and influence senior leadership and attorneys.
  • Strong vendor management skills, with the ability to engage company leadership and influence roadmap decisions where applicable.
  • Excellent problem-solving, project management, and change management skills.
  • Demonstrated ability to manage budgets and allocate resources effectively.
  • Strong communication and presentation skills, with the ability to convey complex concepts to non-technical stakeholders.
BENEFITS

Winston offers comprehensive benefits that provide a full spectrum of coverage and support for our full-time employees and their families. Additional information about benefits and rewards can be found here.

SALARY

The target annual salary range for this role is currently $305,000 - $350,000 based on a regular, full-time schedule. The amount of compensation offered will be determined by several factors, including but not limited to experience, qualifications, market data and internal equity. Total compensation includes a comprehensive healthcare benefits package, yearly retirement contribution, and may include an annual discretionary merit bonus.

We are an equal opportunity employer and welcome applicants from all backgrounds and experiences.#LI-DC2

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