Job Details: Level: Management, Job Location: Chicago Office - Chicago, IL, Salary Range: $175000.00 - $200000.00Salary/year, About Cresset Cresset is a firm built by clients, for clients. As an independent, award-winning multi-family office and private investment firm, we are reimagining the way wealth is experienced. Our purpose is to help ensure that both wealth and life are fully optimized**—integrated, intentional, and aligned with each client’s vision of success.   We provide access to the caliber of talent, ideas, and investment opportunities typically available to the largest single-family offices and institutions. Our approach is personalized, entrepreneurial, and client-first.   Cresset was built to endure. We are creating a 100+ year firm—one focused on delivering an exceptional experience, not only for the families we serve but for the team that serves them. Recognized by Barron’s among the nation’s top multi-family offices,* Cresset is guided by long-term relationships, shared success, and a belief that wealth should serve a life well lived.     Job Description Cresset is seeking a highly execution-oriented Head of AI Engineering & Automation to lead the delivery, integration, and scaling of AI-powered solutions across the firm.   This role is responsible for operationalizing the firm’s AI strategy—translating prioritized initiatives into production-grade workflows, systems, and tools that are embedded into how teams work every day. Reporting to the Chief Technology Officer and working in close partnership with the Head of AI Strategy, this leader ensures that AI initiatives are effectively implemented, adopted, and optimized to deliver measurable business impact.   You will work closely with Technology, Data, and business teams across Advisory, Investments, Client Service, Operations, and Marketing to design, build, and scale AI-enabled capabilities that improve efficiency, enhance client experience, and drive firm-wide productivity.     Key Responsibilities AI Solution Delivery & Execution Own end-to-end delivery of AI initiatives, from requirements gathering through deployment, scaling, and ongoing optimization. Translate prioritized use cases and strategic objectives into actionable implementation plans, technical designs, and deliverables. Ensure AI solutions are production-ready, reliable, and aligned with enterprise architecture standards.   Workflow Automation & Process Transformation Analyze and redesign business processes to incorporate AI, automation, and intelligent workflows. Identify opportunities to reduce manual effort, increase speed, and improve accuracy across core functions. Build scalable frameworks and reusable components to accelerate automation across the organization.   Technology Integration & Architecture Partner with Technology and Data teams to integrate AI capabilities into enterprise systems. Oversee APIs, data pipelines, and system integrations required to support AI-enabled workflows. Ensure seamless interoperability across internally built systems and third-party platforms.   Vendor Implementation & Management Partner with the Head of AI Strategy on vendor selection, then lead implementation, configuration, and ongoing management of AI tools and platforms. Manage relationships with external vendors and development partners to ensure timely, high-quality delivery. Monitor vendor performance and optimize platform utilization to maximize value.   Adoption, Enablement & Change Management Drive firm-wide adoption of AI tools and workflows through training, onboarding, and embedded support. Ensure solutions are intuitive, accessible, and aligned with user needs to maximize engagement and usage. Partner with business leaders to embed AI into team workflows and performance expectations.   Program Delivery & Performance Management Own and maintain a clear, prioritized execution roadmap aligned with the firm’s AI strategy. Establish delivery standards, timelines, and governance for AI and automation initiatives. Track and report on adoption, performance, and ROI of deployed solutions, continuously improving outcomes.   Continuous Improvement & Innovation Stay current on emerging AI tools, automation platforms, and best practices. Rapidly test, iterate, and scale new capabilities to enhance the firm’s AI ecosystem. Support integration of new capabilities into existing systems, including those related to M&A activities.   Partnership with Head of AI Strategy The Head of AI Strategy defines the vision, priorities, and roadmap for AI across the firm. The Head of AI Automation & Enablement owns execution—ensuring those priorities are successfully delivered, adopted, and scaled.   This role serves as the critical bridge between strategy and implementation, providing feedback on feasibility, performance, and adoption to continuously refine the firm’s AI strategy. Qualifications: Qualifications 10+ years of experience in technology delivery, digital transformation, automation, or enterprise systems implementation. Proven track record of delivering and scaling workflow, automation, or AI-driven solutions in complex organizations. Strong hands-on experience with system integrations, APIs, workflow automation tools, and enterprise platforms. Familiarity with AI tools and capabilities, including large language models, copilots, and intelligent automation. Experience managing vendors, implementation partners, and cross-functional delivery teams. Strong program and project management skills, with the ability to execute across multiple concurrent initiatives. Ability to translate business requirements into technical solutions and deliver measurable outcomes.     Preferred Experience Experience in financial services, wealth management, or a regulated industry. Familiarity with enterprise platforms such as Salesforce, Snowflake, Box, and workflow automation tools. Experience with low-code/no-code platforms, RPA, or AI-enabled productivity tools. Background in process engineering, systems architecture, or enterprise integration.     What Success Looks Like AI-powered workflows embedded across core business functions High adoption and sustained usage of AI tools across teams Seamless integration of AI capabilities into enterprise systems Significant reduction in manual processes and operational inefficiencies Measurable improvements in productivity, scalability, and client experience     What We Offer: At Cresset, we focus on people first. As a service business, our people are our assets. Engaging our clients and employees is our highest priority.  Starting salary is $175,000 - $200,000.  Salary will be based on factors including, but not limited to, experience, licenses/certifications, industry knowledge, and geographic location. Cresset offers a competitive compensation package including an annual incentive and a benefits package to all full-time employees including medical, dental, vision, life insurance, 401(k) retirement plan, health savings accounts, short and long-term disability insurance, voluntary critical and accident insurance, and pre-tax parking and transportation programs.     Equal Employment Opportunity It is the policy of Cresset to ensure equal employment opportunity (EEO) for all employees and applicants for employment without regard to race, color, religion, sex, pregnancy (including childbirth, lactation, or related conditions), national origin or ancestry, age, disability, veteran status, uniformed servicemember status, sexual orientation, gender identity, status as a parent, genetic information (including testing and characteristics), or any other characteristic protected by applicable federal, state, or local law. It is Cresset’s policy to comply with applicable laws concerning the employment of persons with disabilities, including reasonable accommodation for applicants and employees with disabilities.     Everything Starts With Culture.   Our Vision We exist to optimize wealth and elevate life—giving clients the time, clarity, and trusted partnership to pursue what matters most.   Our Values                     *Disclosures related to awards, recognitions, and rankings available here.   *Barron's Top 100 RIA Firms (issued 09.2026). Based on data from July of the prior year through June of the award year. Rankings are determined using a proprietary methodology that considers qualitative and quantitative factors. Cresset paid a licensing fee to use the Barron's award logos.   **Wealth Optimized, Life Elevated refers to the firm’s philosophy and process in providing advisory and planning services and is not intended to convey a guarantee of results.   Cresset refers to Cresset Capital Management, LLC and its respective direct and indirect subsidiaries and controlled affiliates. For a full list of Cresset subsidiaries and controlled affiliates, please see cressetcapital.com/disclosures/.