Sedgwick logo

Deputy General Counsel, Global Head of Legal Enablement & Strategic Transactions

Sedgwick

Naperville, ILJob$240–300K/yrSeen todaySeen in employer's feed today

Most applications go out cold — see where you stand first. No sign-up to start.

You apply on the employer's site, with no Olive account needed.

Watch jobs like this.

Don't just apply. Show up ready.

Olive works from this exact posting.

At a glance

Compensation
$240–300K/yr
Location
Naperville, IL
Work Authorization
Not specified

Olive lists jobs from US employers, including remote roles you can work from the United States.

Requirements

Credentials this posting asks for.

Active U.S. State Bar LicenseDoctorate

Job overview

The Deputy General Counsel leads Sedgwick’s Legal and Compliance Organization’s enablement and strategic transactions function. The role modernizes legal and compliance operations and embeds strategic counsel within business units, advising leaders on commercial, technology, and transactional matters. It partners closely with the Global Chief Legal Officer to anticipate risk, inform business decisions, and create value across the enterprise and for clients.

Skills & qualifications

RequiredNice to have

Skills

Oral CommunicationWritten CommunicationPresentation SkillsBusiness AcumenLegal Risk TranslationLegal TechnologyLegal OperationsCommercial Agreement NegotiationM&a TransactionsAI LawPrivacy LawData Governance LawAI GovernanceDigital EthicsAnalytical SkillsInterpretive SkillsOrganizational SkillsProject ManagementInterpersonal SkillsNegotiationManagementLeadershipTeam BuildingGlobal CollaborationTransformation ManagementChange ManagementArtificial IntelligencePrivacyData Governance

Qualifications

J.D. From Accredited Law SchoolActive U.S. State Bar License15+ Years Legal ExperienceLegal Team Leadership ExperienceSenior Executive Advisory ExperienceComplex Regulated Organization ExperienceMultinational Organization ExperienceAI ExperiencePrivacy ExperienceData Governance ExperienceLegal Technology Experience

Benefits

Medical Insurance
Dental Insurance
Vision Insurance
401(k) Match
Paid Time Off

Full job description

Naperville, IL

R80345

By joining Sedgwick, you'll be part of something truly meaningful. It’s what our 33,000 colleagues do every day for people around the world who are facing the unexpected. We invite you to grow your career with us, experience our caring culture, and enjoy work-life balance. Here, there’s no limit to what you can achieve.

Newsweek Recognizes Sedgwick as America’s Greatest Workplaces National Top Companies

Certified as a Great Place to Work®

Fortune Best Workplaces in Financial Services & Insurance

Deputy General Counsel, Global Head of Legal Enablement & Strategic Transactions

PRIMARY PURPOSE : The Deputy General Counsel, Global Head of Legal Enablement & Strategic Transactions leads the Legal and Compliance Organization's Enablement and Strategic Transactions function, with a dual mandate. The first is modernizing and running legal and compliance operations, meaning the processes, technology, metrics, and workflows that allow the legal and compliance department to operate efficiently at scale. The second is embedding strategic legal counsel directly into the business to identify, structure, and create value for Sedgwick and its clients. This role serves as a trusted advisor to business leaders across Sedgwick's claims and risk administration operations, translating complex commercial, technology, and transactional matters into practical guidance. Partners closely with the Global Chief Legal Officer to advance the legal and compliance department as an enterprise intelligence center, serving as a function that anticipates risk, informs business decisions, and creates value across the enterprise and for its clients.

ESSENTIAL FUNCTIONS and RESPONSIBILITIES

Legal and Compliance Operations Leadership

  • Ensures legal and compliance functions operate as generators of enterprise intelligence, with enhanced feedback loops, agile processes, and execution focus.

  • Designs, builds, and runs the legal and compliance department's operating infrastructure, including budgeting, outside counsel management, matter management, legal technology, workflow design, and performance metrics, to support a modern, efficient, and scalable legal and compliance function.

  • Identifies and leads adoption of legal and compliance technology, including AI enabled tools, to improve efficiency, consistency, and visibility across the department.

  • Develops and tracks department-wide metrics and reporting to demonstrate the legal and compliance function's impact and support data-driven decision-making by the Global Chief Legal Officer and executive leadership team.

  • Manages outside counsel relationships, budgets, and alternative fee arrangements to control cost and ensure value.

  • Oversees knowledge management, contract templates and playbooks, and training to standardize and scale legal and compliance support across the enterprise.

  • Strategic Transactions & Commercial Counsel

  • Embeds as a strategic partner within key business units, advising on commercial transactions, strategic partnerships, and new business and product initiatives.

  • Structures, drafts, reviews, and negotiates complex commercial agreements, including client, vendor, technology, and strategic partnership agreements, to protect the company while enabling growth and new revenue opportunities.

  • Partners with business leaders to identify legal and structural opportunities to create value for Sedgwick's clients, including through new service offerings, contract structures, and commercial models.

  • Advises on mergers, acquisitions, and other strategic transactions as needed, coordinating with outside counsel and internal stakeholders.

  • Anticipates legal and regulatory risk in new and evolving business lines and proposes creative, business-minded solutions.

  • Leverages subject matter experts in critical areas such as AI, privacy, and cyber to quickly and creatively counsel the business on complex or fast-moving matters.

ADDITIONAL FUNCTIONS and RESPONSIBILITIES

  • Performs other duties as assigned.

  • Travels as required

SUPERVISORY RESPONSIBILITIES

  • Provides support, guidance, leadership and motivation to promote maximum performance.

  • Administers company personnel policies in all areas and follows company staffing standards and training recommendations.

  • Interviews, hires and establishes colleague performance development plans; conducts colleague performance discussions.

  • Builds and leads a team spanning legal and compliance operations professionals and commercial/transactional attorneys.

QUALIFICATIONS

Education & Licensing

J.D. from an accredited law school required. Active license to practice law and membership in good standing with at least one U.S. state bar required.

Experience

Fifteen (15) or more years of progressively responsible legal experience, including significant experience in legal and compliance operations, complex commercial transactions, mergers and acquisitions, and strategic business advisory, required. Demonstrated experience leading legal teams and advising senior executives within a complex, highly regulated and/or multinational organization required. Experience with artificial intelligence, privacy, data governance, and legal technology preferred.

Skills & Knowledge

  • Excellent oral, written, and presentation skills

  • Strong business acumen; translates legal and compliance risk into practical guidance

  • Experience with legal and compliance technology and operations best practices

  • Experience structuring and negotiating complex commercial agreements and M&A transactions

  • Working knowledge of AI, privacy, and data governance law, including AI governance and digital ethics

  • Analytical and interpretive skills

  • Strong organizational and project management skills

  • Excellent interpersonal and negotiating skills

  • Proven management/leadership skills, including building and scaling teams

  • Effective across a highly matrixed, global organization

  • Experience with transformation and change management

  • Ability to meet or exceed Performance Competencies

WORK ENVIRONMENT

When applicable and appropriate, consideration will be given to reasonable accommodations.

Mental : Clear and conceptual thinking ability; excellent judgment, troubleshooting, problem solving, analysis, and discretion; ability to handle work-related stress; ability to handle multiple priorities simultaneously; and ability to meet deadlines

Physical : Computer keyboarding, travel as required

Auditory/Visual : Hearing, vision and talking

The statements contained in this document are intended to describe the general nature and level of work being performed by a colleague assigned to this description. They are not intended to constitute a comprehensive list of functions, duties, or local variances. Management retains the discretion to add or to change the duties of the position at any time

PAY TRANSPARENCY

As required by law, Sedgwick provides a reasonable range of compensation for roles that may be hired in jurisdictions requiring pay transparency in job postings. Actual compensation is influenced by a wide range of factors including but not limited to skill set, level of experience, and cost of specific location. For the jurisdiction noted in this job posting only, the range of starting pay for this role is $240,000 - $300,000. A comprehensive benefits package is offered including but not limited to, medical, dental, vision, 401k and matching, PTO, disability and life insurance, employee assistance, flexible spending or health savings account, and other additional voluntary benefits.

Sedgwick is an Equal Opportunity Employer and a Drug-Free Workplace.

If you're excited about this role but your experience doesn't align perfectly with every qualification in the job description, consider applying for it anyway! Sedgwick is building a diverse, equitable, and inclusive workplace and recognizes that each person possesses a unique combination of skills, knowledge, and experience. You may be just the right candidate for this or other roles.

Sedgwick is the world’s leading risk and claims administration partner, which helps clients thrive by navigating the unexpected. The company’s expertise, combined with the most advanced AI-enabled technology available, sets the standard for solutions in claims administration, loss adjusting, benefits administration, and product recall. With over 33,000 colleagues and 10,000 clients across 80 countries, Sedgwick provides unmatched perspective, caring that counts, and solutions for the rapidly changing and complex risk landscape. For more, see sedgwick.com

How this job compares

Set against the 2,724 open Legal Counsel jobs on Olive Jobs, counted November 7, 2026.

Pay
  • This posting$240–300K/yr
  • Illinois median$170–228K/yr78 salary ranges
  • US median$155–231K/yr2,050 salary ranges

This range's midpoint, $270K, is 37% above the Illinois median midpoint ($196K) — in the top quarter of Legal Counsel salary ranges in Illinois.

Openings
Olive Jobs lists 95 open Legal Counsel jobs in Illinois and 2,724 across the US. 11% of them nationwide are listed as remote or flexible.
Hiring the most in Illinois
Experience
This posting asks for at least 15 years of experience — more than three in four Legal Counsel postings that state a minimum ask for (median 5 years, across 2,420 postings).
Education
This posting asks for a doctorate or professional degree; 1,967 of the 2,724 open Legal Counsel jobs (72%) ask for a doctorate or professional degree.

Counted across the open, public US postings on Olive Jobs on November 7, 2026. Pay medians are the middle values of the low ends and of the high ends of postings that list both ends of a range in the same cadence (a yearly salary or an hourly rate); a range's midpoint is halfway between its ends. Pay and experience figures resting on fewer than 20 postings are left out.

Prepare for this role

You've read the whole posting — now see how you match it.