Director Machine Learning Jobs in Chicago, IL (NOW HIRING)

At Allstate, great things happen when our people work together to protect families and their belongings from life's uncertainties. And for more than 90 years, our innovative drive has kept us a step ahead of our customers' evolving needs. From advocating for seat belts, air bags and graduated driving laws, to being an industry leader in pricing sophistication, telematics, and, more recently, device and identity protection.
Job Description
Why This Role
This is a signature seat within the enterprise P&C actuarial organization - a role designed for a senior reserving leader who wants direct line-of-sight to the top of the house. You will own the estimation of loss and expense reserves across Auto Injury and Business Insurance, and you'll do it with a rare combination of technical depth, executive influence, and enterprise reach.
You'll have opportunities to regularly present to senior and executive level leadership up to and including the CEO, along with coordinating with and supporting the external appointed actuary, auditors, and state departments of insurance. In short: your work will be seen, challenged, and acted upon at the highest levels of the company.
As a Director, you won't just deliver results - you'll shape culture, sharpen the craft, and set the standard for how modern reserving is done. We value in-person, connected experiences with your team and Allstaters across the enterprise, which will require travel within your local area or to one of our offices on a regular basis.
What You'll Do

• Own the reserve estimate. Develop, execute, and continuously improve highly complex actuarial reserving methodologies across multiple lines of business, ensuring data quality, methodology appropriateness, and documentation standards are best-in-class.
• Influence the enterprise. Present at Loss Reserve Committee meetings and translate complex actuarial results into clear, decision-ready insights for the CFO, Chief Accounting Officer, and CEO, as well as business unit presidents and finance leadership.
• Benchmark and modernize. Continuously benchmark reserving techniques against industry practice and bring forward the next generation of methods - from stochastic models to machine learning and AI-enabled reserving.
• Engage external stakeholders. Serve as a primary point of contact for auditors, the external appointed actuary, and state departments of insurance; represent the company with credibility and command.
• Lead reserving in dynamic environments. Review and challenge complex loss reserving techniques across multiple lines and provide expert consultation on the most difficult reserving questions.
• Build the team. Own end-to-end talent management for an expanded team - succession planning, compensation, development, bench strength, and organizational design - and coach the next generation of reserving leaders.
• Set strategy. Connect Allstate's vision and enterprise strategies to department initiatives; develop and lead multi-year plans that drive measurable corporate business results.
• Ensure control and compliance. Develop and adhere to internal and external compliance requirements, including GAAP, Statutory, and evolving regulatory expectations around model governance and AI.

Executive Exposure & Impact
This role sits close to the decision-making core of the company.
Your voice will shape how the company communicates reserve adequacy to the Board, the Street, and regulators.
What You'll Bring
Education & Credentials

• Bachelor's degree (preferred); equivalent combination of education and experience will be considered.
• Fellow of the Casualty Actuarial Society (FCAS) or equivalent actuarial designation(required).
• 12+ years of progressive P&C actuarial experience, with meaningful depth in reserving.

Technical & Analytical Skills

• Deep expertise in loss reserving methodologies (chain-ladder, Bornhuetter-Ferguson, Cape Cod, stochastic reserving, individual claim-level models) and advanced actuarial/statistical techniques.
• Strong knowledge of insurance reserving frameworks, ERM, capital, and regulatory requirements (GAAP, Statutory).
• Ability to quickly master and apply a broad range of analytical tools, data sources, and software applications.z

AI & Advanced Analytics Proficiency

• Working proficiency with AI, machine learning, and generative AI as applied to reserving and broader actuarial work - including automated assumption selection and LLM-assisted documentation, analysis, and communication.
• Familiarity with AI governance and model risk management frameworks (e.g.,CAS AI guidance) and the ability to responsibly deploy AI in a regulated environment.
• Comfort using AI/GenAI tools (e.g., Copilot, Python/R ML libraries) to accelerate model development, benchmarking, exhibits, and executive-ready reporting.

Executive Communication & Influence

• Exceptional communication skills - able to craft and deliver clear, compelling, executive-ready messages, and to translate highly technical concepts for CFO/CAO/CEO-level audiences.
• Proven ability to influence upward, downward, and laterally; builds alignment and drives outcomes without relying on positional authority.
• Coaches others on the proper use of technical and analytical language and serves as a subject-matter expert to internal partners.

Leadership & Management

• Proven leadership experience, including developing people leaders and building high-performing actuarial teams.
• Leads with empathy and clarity through organizational changes; builds trust and sustains engagement in an evolving company environment.

Project & Program Management

• Advanced program management capability, with a track record of independently leading multiple high-complexity, cross-functional initiatives on time and on quality.

Supervisory Responsibilities
This role has direct supervisory responsibility for a team of actuarial leaders and analysts across Auto Injury and Business Insurance.
Skills
Business Strategies, Data Analytics, Performance Management (PM), Strategic Leadership, Strategy Development
Compensation
Compensation
Compensation offered for this role is 190,000.00 - 250,000.00 annually and is based on experience and qualifications.
The candidate(s) offered this position will be required to submit to a background investigation.
Joining our team isn't just a job - it's an opportunity. One that takes your skills and pushes them to the next level. One that encourages you to challenge the status quo. One where you can shape the future of protection while supporting causes that mean the most to you. Joining our team means being part of something bigger - a winning team making a meaningful impact.
Allstate generally does not sponsor individuals for employment-based visas for this position.
Effective July 1, 2014, under Indiana House Enrolled Act (HEA) 1242, it is against public policy of the State of Indiana and a discriminatory practice for an employer to discriminate against a prospective employee on the basis of status as a veteran by refusing to employ an applicant on the basis that they are a veteran of the armed forces of the United States, a member of the Indiana National Guard or a member of a reserve component.
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Allstate provides a comprehensive technology setup, including a laptop, monitors, headset, keyboard, and mouse. Employees eligible to work from home also receive a monthly connectivity reimbursement to help offset internet costs.
When working from home, you must have a dedicated, private workspace free from distractions, along with appropriate desk and seating. Reliable internet is required, with minimum speeds of 50 MB download and 5 MB upload.