Managing Director - Risk Advisory

About the role

We are an advisory firm dedicated to Core Values of collaboration, enthusiasm, generosity, and perseverance. Our services span accounting and risk, technology-enabled transformation, and transactions. We partner with clients to solve challenges and deliver value.

Responsibilities

• Expand CrossCountry’s Risk Advisory presence in the Chicago market through strategic relationship development and targeted business development efforts
• Originate new client relationships leveraging existing local, Midwest, and national networks and introductions from leadership
• Develop and execute go-to-market activities and shape our Chicago risk growth strategy aligned to priority industries and buyer needs
• Lead complex risk transformation, operational risk, and enterprise risk engagements for commercial and private equity/growth-oriented organizations
• Design and implement operating models, governance structures, and internal control frameworks that support business objectives
• Provide senior-level advisory across risk domains, balancing risk management, operational effectiveness, and strategic enablement
• Contribute to developing and implementing firm-approved, AI-enabled solutions for clients, in accordance with company policies on data protection, intellectual property, and professional standards
• Stay informed about emerging AI tools and techniques and collaborate with firm leadership to identify and champion compliant opportunities to enhance client solutions and internal processes
• Oversee client accounts and engagements, serving as an escalation point for complex delivery, commercial, and team matters
• Proactively identify and resolve risks, issues, and dependencies across client engagements
• Coach and develop teams by setting clear objectives, providing feedback, and fostering a culture of continuous improvement and innovation
• Contribute to the evolution of Risk Advisory offerings, methodologies, and talent strategy

Requirements

• Proven ability to originate and close advisory work with portable Chicago relationships and a measurable track record of revenue generation
• Extensive experience in Risk Consulting, Operational Risk, and Risk Transformation, including enterprise risk management (ERM), operational resilience, and internal control design
• 15+ years in advisory roles with team leadership experience and a track record of leading large complex programs/transformation efforts and multi-disciplinary teams
• Ability to advise and influence at the C-suite level and collaborate across risk, technology, governance, and transformation domains
• Comfort with AI: Demonstrated ability to responsibly explore and adopt firm-approved AI tools to enhance productivity and innovation
• A continuous learning mindset and openness to evolving methodologies, technologies, and client needs
• An entrepreneurial approach with the ability to build offerings, teams, and long-term client relationships in a growth-oriented environment

Qualifications

• Bachelor’s degree in Accounting, Finance, Business, Engineering or related field
• Certifications such as CIA, CISA, CCSA, CPA, CRMP, and CRISC preferred
• Willingness to travel up to 30% (varies by client)
• Ability to work a hybrid schedule out of our Chicago office

Benefits

Our benefits package includes comprehensive healthcare options, including medical, dental, and vision coverage; flexible spending accounts; and a 401(k) with company matching. Additionally, employees can take advantage of generous parental and maternity leave policies, technology stipends, and wellness reimbursement programs, all designed to support both professional growth and personal well-being.

For detailed information about benefits at CrossCountry, please visit our dedicated benefits site: here.