Freelance Operational Risk Manager Jobs in Naperville, IL

Chief Risk Officer

CFTC-Regulated Business Unit

Location: Chicago, IL. Fully remote to start, transitioning to 3 days/week in office.

About Smarkets

Smarkets is a prediction market exchange for sports and political trading that has handled over $50 billion in volume since 2010. We are upending the sports betting industry by growing a platform that offers the best value for traders, with not only the fairest prices but also the best technology, alongside a superior customer experience.

We believe the foundation to our success is attracting the best people to our organisation and creating a high-performance environment where they can thrive. We are searching for an atypical candidate with a wealth of regulated business experience to support the development of our CFTC business.

This is a senior leadership role sitting within our CFTC-regulated business unit, with responsibility for the enterprise risk management function across our Designated Contract Market (DCM) and Derivatives Clearing Organization (DCO). You will be the most senior risk voice in the business, owning the identification, assessment, and mitigation of every risk facing the entity. This is a founding build: our licensing applications are in‑flight and you will stand up the risk management framework from the ground up through to go‑live, then operate and mature it as the business scales. You will work directly with the CEO and board, with the support of the Smarkets UK team behind you.

• Senior risk leader with 7+ years of senior experience in risk management, ideally within derivatives markets, exchanges, clearinghouses, or other financial infrastructure providers.

• 4+ years of hands‑on experience owning enterprise or operational risk within a DCM, DCO, or comparable regulated market infrastructure in the United States, with direct responsibility for risk and system safeguards, not advisory or supporting experience.

• Entrepreneurial mindset with a proven track record working in a small scale fast‑paced creative work environment.

• Deep understanding of the CFTC's risk and system safeguards expectations, including Core Principle 20 (System Safeguards), stress testing, and operational resilience requirements.

• Strong background identifying and analysing technology risk, counterparty exposures, and internal control weaknesses, and translating them into a defensible, audit‑ready risk framework.

• Proficiency with established risk assessment frameworks (COSO ERM, ISO 31000) and control testing, applied across financial, operational, and systemic risk. CFA or FRM certification is desirable.

• Experience partnering with the CEO and board on risk strategy, board‑level governance, and risk reporting, including engagement with regulators at an institutional level.

• Own the end-to-end enterprise risk management programme for Smarkets Board of Trade (DCM): policies, controls, monitoring, stress testing and reporting, ready for go‑live.

• Establish and maintain risk assessment processes across market volatility and trading disruptions, technology failures and cyber threats, vendor and third‑party dependencies, and compliance and internal control weaknesses.

• Own Core Principle 20 (System Safeguards): embed system safeguards testing, cyber resilience, business continuity and recovery planning into day‑to‑day operations.

• Oversee or conduct stress testing and backtesting relevant to market and technology risk, and maintain the risk register with clear escalation of significant events to the CEO and regulatory authorities.

• Develop risk mitigation strategies and monitor risk indicators across all business units, including those operating across jurisdictions (for example, engineering in the UK).

• Work in coordination with the CISO and Compliance to ensure regulatory and operational risk is fully embedded across the business.

• Report on risk exposures and mitigation plans to the CEO, board, and designated risk committees, ensuring documentation, dashboards and controls are audit‑ready and CFTC‑compliant.

• Contribute to incident response and recovery planning, with a focus on risk impact analysis and controls testing.

• Personal interest in sports, exchanges, or trading

• Experience with system safeguards testing, cybersecurity risk, and business continuity and disaster recovery planning in a regulated trading environment.

• Experience engaging with self‑regulatory organisations (SROs) such as the NFA, and participating in industry working groups.

• Prior experience at the CFTC as a staff member or examiner, subsequently transitioning to industry, this background is highly valued.

• Familiarity with event contracts, prediction markets, or similar novel futures products and their treatment under the CFTC framework.

• Push to win

• Make others better

• Give a shit

• Be a pro

• Bring the energy

Our values are at the heart of everything that we do. We believe these are the fundamentals to ensure we are delivering what's expected of us in the best way possible for ourselves and for those around us.

We offer a competitive salary package and benefits, along with a dynamic and collaborative work environment. Your work with us will make an impact and your voice will be heard. We are a diverse team with a strong work ethic and plenty of hunger to win. We have designed our benefits offering around Health, Wealth, Lifestyle and Development.