Head Risk Management Jobs in Chicago, IL (NOW HIRING)

About Us
DriveWealth is on a mission to make investing easier. We believe that everyone should have the ability to control their financial future, and that access to financial markets should not be limited by geography, wealth, or legacy systems. We are a global B2B financial technology organization dedicated to democratizing access to financial independence around the world. Our mission is realized through an API-based platform, empowering our partners to offer seamless investing and trading experiences to clients worldwide, all from their mobile devices. Our technology provides partners with a modern, extensible toolkit, enabling traditional investment workflows and innovative techniques like fractional share ownership. DriveWealth has evolved into a global platform offering trading of US equities, mutual funds, ETFs, fixed income, and options.
There's never been a better time to build a category-defining business and there has rarely been a team better positioned for this opportunity. Our culture blends the pace and agility of a fintech start-up with the impact, stability, and discipline of Wall Street. We encourage creativity and experimentation while ensuring institutional-grade execution and regulatory compliance in everything we do. Join us and help build the future of global investing!
About The Role
Reporting to the Head of Risk Management, the Lead of Operational & Technology Risk owns the enterprise operational and resiliency risk program across a regulated, globally distributed brokerage platform.
This is a builder's role. You will design the operational risk framework, including the enterprise risk taxonomy and appetite structure, stand up risk assessment and control assurance programs, own issue and risk event management, and build AI-native tooling that makes risk management faster, sharper, and practical for the people who actually own it.
Success requires someone who thrives with autonomy, builds risk practices that hold up under scale and regulatory scrutiny while still letting the business move quickly, and can translate operational risk into decisions the business, executives, and the Board will act on. You will partner closely with Engineering, Product, Operations, Treasury, Security, Legal, and Compliance, which separately owns programs that integrate with the firm-wide operational risk framework.
What You'll Do
Build and Own the Operational Risk Framework

• Build the enterprise operational risk taxonomy, risk appetite statements, and supporting policy architecture.
• Establish and lead the operational risk and resiliency forum, driving genuine challenge and alignment rather than status review.
• Produce reporting to the Global Risk Committee and the Board that carries a clear point of view and prompts decisions.
• Establish decision frameworks, escalation thresholds, and exception governance that hold under regulatory and partner scrutiny.

Get Ahead of Change, New Products, and New Markets

• Own risk assessment for new products, partners, markets, and platform capabilities, including emerging asset classes, tokenized securities, and international market entry.
• Build a change risk process that accelerates safe launches rather than create unnecessary friction.
• Establish and run the RCSA program across a global, partner-dependent operating model.
• Serve as a risk advisor to Operations, Product, Security, and Engineering leaders throughout the product development lifecycle.

Set the Enterprise Standard and Assure Controls

• Own the enterprise methodology every risk program conforms to, including taxonomy, rating scale, assessment approach, defense in depth control framework, and KRI design conventions.
• Build the operational control testing program covering ICOC and key operational controls, including methodology, sampling, deficiency classification, and remediation tracking to closure.
• Aggregate output from programs executed by other assurance functions into a single enterprise risk picture, and challenge results that do not reconcile.
• Own operational resiliency, business continuity, and disaster recovery, recognizing DriveWealth is itself critical infrastructure to its partners.

Close the Loop on Issues, Risk Events, and Indicators

• Own enterprise issue management end to end, including methodology, intake, classification, corrective action, aging thresholds, and escalation.
• Build the risk event and loss database, lead root cause analysis on material events, and ensure learnings feed back into risk assessments and control design.
• Design a KRI framework tied to how the platform actually runs, including trade and settlement volume, availability, partner onboarding, and operational capacity.

Build AI-Native Tooling and Enablement for Risk Practices

• Use automation and AI to move control testing from sample-based toward full-population where the data supports it, and to automate evidence collection and exception triage.
• Build risk tooling first-line owners genuinely want to use, and treat low adoption as a design failure rather than a compliance problem.
• Scale the program through tooling leverage rather than headcount.

Lead, Scale, and Develop the Team

• Hire, coach, and develop a team of technically fluent risk professionals, setting a high bar for ownership, judgment, and execution.
• Build a risk champion network across first-line functions so the program scales through the business.
• Build a culture of bias for action, technical curiosity, and pragmatic risk decision-making.
• Represent Risk Management with regulators, auditors, and enterprise partners.

You Bring
10+ years in operational, technology, or enterprise risk management, with significant time in a regulated financial services environment and prior ownership of a risk program.
Demonstrated experience building a risk function from an early stage, not only operating an established one.
Deep working knowledge of RCSA, control testing, issue management, KRI design, and risk event management.
Practical fluency with agentic AI applied to risk work, with real examples of what you have built or deployed. Hands-on coding is not required, but technical depth is.
Strong, practical understanding of broker-dealer operations and regulatory expectations across SEC, FINRA, CFTC, and NFA.
Experience setting enterprise risk methodology that specialist programs, such as AML, cyber, privacy, or vendor risk, execute against.
Proven ability to lead cross-functional initiatives and influence engineering and product organizations without formal authority.
Excellent written and verbal communication, including the ability to write for a Board audience and hold a room with senior leadership.
Special Knowledge (Nice To Have, Not Required)

• Experience at a broker-dealer, clearing firm, fintech, or embedded-finance / brokerage-as-a-service platform
• Exposure to digital assets, tokenization, event contracts, or emerging market structure
• Experience in a B2B or platform business where clients depend directly on your operational resiliency
• Multi-jurisdiction or cross-border regulatory experience
• Hands-on experience with GRC/IRM platforms, BI and visualization tooling, or agentic AI frameworks.
• Relevant certifications: FRM, CRMA, CISA, CRISC, or comparable
• Advanced degree in a business, technical, or quantitative field

Location
This role is open to candidates in the following locations: New York City, NY or Chicago, IL - Hybrid

• This role is expected to come into the office on a cadence set by the Hiring Manager/Team.
• If you're not based in one of the locations listed above, this role is not a fit, and we cannot accommodate remote work outside these locations.
• Applicants must be authorized to work for any employer in the U.S. DriveWealth does not sponsor or take over sponsorship of an employment visa at this time.

Pay Range: $200,000 - $215,000 USD
Working at DriveWealth
We do our best work when we're in the same room. To maintain the speed our partners expect, our New York, Chicago, and Lithuania teams work in office on a hybrid schedule. We've found that being physically side-by-side is the only way to solve complex problems in real-time and stay truly accountable to the products we ship. When you're here, you're working directly with the people making the decisions.
To support that work, we provide competitive compensation, equity, and a 401(k) match. We also offer Medical insurance, Dental insurance, Vision insurance, Disability insurance, and Paid Parental Leave, along with a wellness reimbursement, a company-provided phone, and a personal development allowance. Finally, we value the time you spend away from the office with generous Paid Time Off (PTO) and observed holidays.
Work Authorization
Applicants must possess the legal right to work in the country where the position is located at the time of application. DriveWealth requires all employees to provide original documentation verifying their work authorization on or before their first day of employment.
For US-based roles: Applicants must be currently authorized to work in the United States on a full-time basis without the need for current or future visa sponsorship. DriveWealth does not provide visa sponsorship or support for employment authorization, including transfers, at this time. Offers of employment are strictly contingent upon an individual's ability to secure and maintain the legal right to work at the Company.
How We Think About AI
We leverage AI to work smarter and move faster. We seek AI-curious talent who are proactive about using emerging tools to increase signal quality, reduce friction, and improve outcomes to deliver products faster, provide better service to our partners, and to streamline processes. Your ability to leverage our internal tools and technology to drive results is as important to us as your core domain expertise.
Compensation
Pay is generally based on the level, complexity, responsibility, location, and job duties/requirements of the specific position. We then source candidates with the requisite skills, expertise, education, training, and experience. If you are selected for an interview, please feel welcome to speak to a recruiter about our compensation philosophy and other available benefits. This role is eligible for base, bonus, equity, 401(k) match, and heavily subsidized benefits and perks.
Equal Employment Opportunity
To build technology and products that are used and loved by people and solve real-world problems, we need to build a team with many different perspectives and experiences. We are an equal opportunity employer. We do not discriminate based on race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We encourage candidates from all backgrounds to apply.
Agency Disclaimer
DriveWealth does not accept agency resumes. Do not forward resumes to our jobs alias, employees, or any other organization location. DriveWealth is not responsible for any fees related to unsolicited resumes.